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Chen, Gaoyum. "Lanthanide complexes of phthalimide and phthalamate containing ligands : synthesis, photophysical properties and their potential applications." Thesis, London Metropolitan University, 2012. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.571268.
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Molecular sensors and switches have made important contributions to biomedical devices and molecular computational operations. There are numerous molecular designs using a fluorophore linked through a spacer group to a receptor(s), with a wide dynamic range, directional precision, target specificity, and molecular logic capability. Tb(III) and Eu(III) metal ions have natural luminescence lifetimes in the order of milliseconds. As a result they have been used as probes that allow discrimination between probe emission and background fluorescence using time- resolved techniques. Unfortunately the free ions themselves absorb light poorly so cannot provide the sensitivity often required of a probe or a sensor. Their performance however can be improved dra.matically by the coordination of the metal ions to organic chelate ligands containing appropriate organic fluorophores. This project is based on the design and synthesis of Tb(lU) and Eu(III) complexes of phthalimide and phthalamate derivatives as responsive lanthanide complexes. Phthalimide and phthalamate compounds are organic chromophores. Four acyclic phthalimide derivatives, Ll, L3, LS and V, were prepared through condensation reaction of phthalic anhydride and the corresponding amine derivatives in glacial acetic acid. These phthalimide derivatives, Ll, L3, LS and V, were then hydrolysed under basic conditions to yield the desired phthalamate compounds, L2, L4, L6 and L8. The yields of these phthalamate derivatives (L2, L 4, L6 and L8) were 50%-70%. They are fully characterised by lH and 13C NMR spectroscopy, elemental analysis, mass spectrometer, IR and melting point analysis. A series of macrocycles with N-substituted phthalimide pendant arm(s) L9-12were synthesised. The macrocyclic phthalimide derivatives were prepared by incorporating N-bromoalkyl phthalimide onto tri-tert-butyl-1,4,7,10- tetraazacyclododecane-1,4,7 -triacetate, di-tert-butyl-1,4,7,10- tetraazacyclododecane-1,4-diacetate and mono-tert-butyl-1,4,7,10- tetraazacyclododecane-monoacetate through nucleophilic substitution reactions. Removal of t-butyl functions and retention of phthalimide was achieved in trifluoroacetic acid to yield the final products (6%-14%). 1,4,7,10- Tetraazacyclododecane was alkylated on its 4 nitrogen sites by phthalimide function with a propyl bridge to yield L13 (10%). L9-13 were fully characterized by lH and 13C NMR spectroscopy, elemental analysis, mass spectrometer, IR and melting point analysis. Apart from Ll, L3, L4, LS and LlO all the phthalimide and phthalamate derivatives synthesised in this thesis are new. The optimal metal-to-ligand ratio of 1:2 was established for acyclic phthalamate- based terbium complexes, whereby the best antennae effects on the luminescence properties of these complexes were observed. The highest luminescence level of [Tb(L2)2J-, [Tb(L4)2J-, [Tb(L6)2P- and [Tb(LB)2]- was observed at pH ea. 6, but it was quenched at pH> 7. These four terbium complexes exhibited long emission lifetimes of the order of sub-milliseconds. Luminescence features of [TbL9], [TbLlO], [J'bLll]+ and [TbLl2)2+ showed rather weak luminescence under acidic conditions. The luminescence was enhanced under basic conditions while phthalimide functions were hydrolysed to phthalamates. Their phthalamate-based macrocyclic terbium complexes ([TbL9H]-, [TbLlOH]-, [TbLllHJ-, [TbLl2H]-, and [TbL13H]-) exhibited high quantum yields (cp) and long lifetimes (T) of the order of milliseconds at pH ea. 6. The values of
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Zhao-Karger, Zhirong. "The first anionic thia-Fries rearrangement at arene tricarbonylchromium complexes and reactions of phthalimide tricarbonylchromium complexes." [S.l.] : [s.n.], 2006. http://deposit.ddb.de/cgi-bin/dokserv?idn=983769435.
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Wang, Zhengfang. "Thiol Protein/Peptide Modification by N-(Phenylseleno)phthalimide and Applications of Chemometrics in Organic Food Authentication." Ohio University / OhioLINK, 2014. http://rave.ohiolink.edu/etdc/view?acc_num=ohiou1395159533.
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Manley-King, Clarina Ilara. "The synthesis and evaluation of phthalimide analogues as inhibitors of monoamine oxidase B / Clarina Ilara Manley-King." Thesis, North-West University, 2011. http://hdl.handle.net/10394/8506.
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Parkinson’s disease (PD) is a multifactorial neurodegenerative disease believed to be caused
by a number of factors. This has made the successful treatment of the disease very difficult, as
the underlying cause of degeneration is still unknown. Monoamine oxidase (MAO-B) inhibitors
have been used in the treatment of PD. MAO-B is known to be involved in the catalytic oxidation
of biogenic amines, a reaction which produces aldehydes and hydrogen peroxide as byproducts.
Both these by-products can be toxic if not rapidly cleared. Inhibitors of MAO-B
conserve the depleted supply of dopamine and also stoichiometrically decreases the amount of
toxic by-products formed. Thus, MAO-B inhibitors may offer both symptomatic and
neuroprotective effects that can aid in the treatment of PD.
This study is part of the ongoing investigation into the development of new selective reversible
inhibitors of MAO-B. Literature reports that isatin, a small, reversible, endogenous MAO
inhibitor, found in the brain, can inhibit both MAO-A and MAO-B enzymes. Previous studies
have shown that (E)-5-styrylisatin and (E)-6-styrylisatin are reversible inhibitors of human MAOA
and -B. Both homologues are reported to exhibit selective binding to the MAO-B isoform with
(E)-5-styrylisatin being the most potent inhibitor. To further investigate these structure–activity
relationships (SAR), in the present study, additional C5- and C6-substituted isatin analogues
were synthesized and evaluated as inhibitors of recombinant human MAO-A and MAO-B. A
series of structurally related corresponding anilines, which are synthetic precursors in the
synthesis of isatin derivatives, were also evaluated as MAO inhibitors. This study is part of an
attempt to identify new inhibitors with enhanced potencies and specificities for both MAO-A or
MAO-B.
In general, C5- and C6-substitution of isatin leads to enhanced binding affinity to both MAO
isozymes, compared to isatin, and in most instances result in selective binding to the MAO-B
isoform. The most potent MAO-B inhibitor 5-(4-phenylbutyl)isatin, exhibited an IC50 value of 0.66
nM and the most potent MAO-A inhibitor was found to be 5-phenylisatin with an IC50 value of
562 nM. Crystallographic and modelling studies suggest that the isatin ring binds to the
substrate cavities of MAO-A and -B and is stabilized by hydrogen bond interactions between the
NH and the C2 carbonyl oxygen of the dioxoindolyl moiety and water molecules present in the
substrate cavities of MAO-A and -B. Based on these observations and the close structural resemblance between isatin and its
phthalimide isomer, a series of phthalimide analogues were synthesized and evaluated as MAO
inhibitors. The results showed that the C5 substituted phthalimides were very potent competitive
inhibitors with IC50 values ranging 0.007 to 2.5 μM for MAO-B and IC50 values ranging 0.22 to
9.0 μM for MAO-A. The 5-(4-benzyloxy)phthalimide was the most potent MAO-B inhibitor in the
phthalimide series, with an IC50 value of 0.007 μM. The results of modelling studies showed that
hydrogen-bond interactions between the phthalimide carbonyl oxygen and the enzyme amino
acid residues and the integral water molecules are important for the binding of phthalimide to
the active site of MAO-B.
The potent competitive inhibition and activities of the C5 substituted phthalimide analogues
towards MAO-B has led us to investigate a structurally similar series of C4-substituted
phthalonitriles. A series of C4-substituted phthalonitriles were prepared and evaluated as
inhibitors of MAO-B. In general, the phthalonitriles were very potent competitive inhibitors of
MAO-B with IC50 values ranging from 0.005–6.02 μM. 5-(4-benzyloxy)phthalonitrile was found to
be the most potent inhibitor for human MAO-B with an IC50 value of 0.005 μM.
To further investigate the effect of the nitrile group in this class of compounds, C3 and C4
substituted benzonitriles were prepared and evaluated for MAO inhibition. The results showed
that similar to the phthalonitriles, the benzonitriles were also potent inhibitors of human MAO-B,
with IC50 values ranging from 0.785-1.39 μM. The benzonitriles, however, were not as potent as
the corresponding phthalonitriles. These findings suggest that, although two nitrile groups are
more optimal for inhibition, the presence of a second nitrile group is not a necessity for potent
MAO-B inhibition. Placement of the nitrile group at C3 resulted in more potent MAO-B inhibition
compared to placement of the nitrile at C4.Thesis (Ph.D. (Pharmaceutical Chemistry))--North-West University, Potchefstroom Campus, 2012
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Molitor, Sabrina [Verfasser]. "Aromatische Carbonsäureimide und -diimide in Photoinduzierten Elektronentransfer-Prozessen: Photodecarboxylative Addition von Carboxylaten durch Phthalimide und Pyromellitdiimide / Sabrina Molitor." München : Verlag Dr. Hut, 2016. http://d-nb.info/1115550292/34.
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GOMES, Paulo André Teixeira de Moraes. "Planejamento estrutural, síntese e avaliação das propriedades farmacológicas de inéditas tiazolil-hidrazonas derivadas da ftalimida e da isatina." Universidade Federal de Pernambuco, 2016. https://repositorio.ufpe.br/handle/123456789/18462.
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FACEPE
A identificação e utilização de estruturas privilegiadas como base para a obtenção de novas moléculas, tem se destacado como estratégia para a descoberta de novos fármacos. Como exemplos de estruturas privilegiadas podem ser citados os heterociclos ftalimida e isatina. Ambos são importantes grupos farmacofóricos conhecidos pelo amplo espectro de atividades biológicas que apresentam. Outro importante grupo farmacofórico que vem sendo bastante explorado e que está presente em moléculas quimicamente diversas e ativas para uma grande variedade de doenças é o heterociclo tiazol. Fazendo uso da estratégia de hibridização molecular foram obtidos inéditos compostos tiazóis derivados da ftalimida e da isatina. O presente trabalho está dividido em dois capítulos e explora duas das muitas atividades farmacológicas apresentadas pelos grupos farmacofóricos, a atividade antichagásica e a anticâncer. O primeiro capítulo apresenta o planejamento, a síntese, a caracterização estrutural, a avaliação quanto às propriedades antichagásicas de tiazóis derivados da ftalimida. Alguns dos compostos obtidos nessa primeira parte apresentaram potente inibição sobre a forma tripomastigota do parasito com baixa toxicidade em células esplênicas, e as relações estrutura-atividade resultantes são discutidas. Também são apresentadas alterações ultraestruturais que ftalil-1,3-tiazóis induzem sobre a morfologia do parasito, como o encurtamento do flagelo, condensação da cromatina, inchaço das mitocôndrias, alteração de reservosomos e dilatação do retículo endoplasmático. Juntos, estes dados revelam, pela primeira vez, uma nova série de compostos contendo ftalimido-tiazóis como base estrutural com potentes efeitos contra o T. cruzi e características de líder-similar ("lead-like") contra a doença de Chagas. Os resultados apresentados no primeiro capítulo foram publicados na European Journal of Medicinal Chemistry. O segundo capítulo apresenta o planejamento, a síntese empregada, a caracterização estrutural para a obtenção das séries de tiazóis inéditos derivados da isatina, assim como alguns resultados prévios de suas propriedades antitumorais. Nessa segunda parte da tese são apresentadas 29 moléculas, sendo 9 tiossemicarbazonas e 20 tiazóis. Nenhum dos compostos apresentou citotoxicidade na dose de 100 μM para células normais humanas. Embora não sejam conclusivos, resultados prévios indicam que alguns compostos intermediários apresentam importante atividade antitumoral, o que pode indicar que a síntese de derivados de tais compostos pode ser promissora para a obtenção de novos agentes antitumorais. De modo geral, pode-se concluir que a estratégia de utilização de estruturas privilegiadas como bases estruturais para a obtenção de novos compostos biologicamente ativos permitiu identificar potentes agentes antichagásicos, bem como encontrar um prévio direcionamento para síntese de novos protótipos a fármacos antitumorais.
The identification and use of privileged structures as a basis for obtaining new molecules, has excelled as a strategy for drug discovery. Examples of privileged structures can be cited the phthalimide and isatin heterocycles. Both are important pharmacophore groups known by the broad spectrum of biological activities that present. Another important pharmacophore which has been extensively explored and is present in various chemically active molecules and for a wide variety of diseases is the thiazole heterocycle. Making use of molecular hybridization strategy were obtained unpublished thiazoles compounds derived from phthalimide and isatin. This work is divided into two chapters and explores two of the many pharmacological activities presented by pharmacophore groups, the antichagasic and anti-cancer activity. The first chapter presents the planning, synthesis, structural characterization, antichagasic properties evaluation of phthalimido-thiazoles derivatives. Some of the compounds obtained in this first part showed potent inhibition on parasite trypomastigotes with low toxicity in spleen cells and the resulting structure-activity relationships are discussed. Also ultrastructural changes appear that phthalyl-1,3-thiazoles induce on the morphology of the parasite, such as the shortening of the flagellum, chromatin condensation, swelling of mitochondria, reservosomes change and dilatation of the endoplasmic reticulum. Together, these data revealed, for the first time, a novel series of phthalimido-thiazoles-structure-based compounds with potential effects against T. cruzi and lead-like characteristics against Chagas disease. The results showed in the first chapter were published in the European Journal of Medicinal Chemistry. The second chapter presents the planning, the synthesis used, the structural characterization to obtain the derivatives unpublished thiazoles series of isatin, as well as some preliminary results of its anti-tumor properties. In this second part of the thesis are displayed 29 molecules, 9 thiosemicarbazone and 20 thiazoles. Neither compound showed cytotoxicity in a dose of 100 uM to normal human cells. Although not conclusive, preliminary results indicate that some intermediates have significant antitumor activity, which may indicate that the synthesis of derivatives of such compounds can be promising for obtaining novel anticancer agents. In general, it can be concluded that the strategy of use of privileged structures as structural basis for obtaining new biologically active compounds identified potent antichagasic agents and find a previous guidance for synthesis of new prototypes to antitumor drugs.
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Van, der Walt Mietha Magdalena. "Syntheses of sulfanylphthalimide and xanthine analogues and their evaluation as inhibitors of monoamine oxidase and as antagonists of adenosine receptors / Mietha Magdalena van der Walt." Thesis, North-West University, 2013. http://hdl.handle.net/10394/9537.
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Currently L-DOPA is the drug most commonly used for the treatment of Parkinson’s disease
(PD). However, the long-term use of L-DOPA is associated with the development of motor
fluctuations and dyskinesias. Treatment mainly addresses the dopaminergic features of the
disease and leaves its progressive course unaffected. An optimal treatment would be a
combination of both motor and non-motor symptom relief with neuroprotective properties. Two
drug targets have attracted the attention for PD treatment, namely monoamine oxidase B (MAOB)
and adenosine A2A receptors. MAO-B inhibitors enhance the elevation of dopamine levels
after L-DOPA treatment, improve motor functions and may also possess neuroprotective
properties. The antagonistic interaction between A2A and dopamine receptors in the
striatopallidal pathway, which modulates motor behaviour, has also become a potential strategy
for PD treatment. Blockade of the A2A receptor exerts both anti-symptomatic and
neuroprotective activities and offer benefit for motor symptoms and motor complications. This
thesis seeks to synthesize novel drug treatments for PD by exploring both MAO-B inhibitors and
adenosine A2A receptor antagonists and to assess the prospects for drug modification to
increase activity.
MAO-B inhibitors -
Based on a recent report that the phthalimide moiety may be a useful scaffold for the design of
potent MAO-B inhibitors, the present study examines a series of 5-sulfanylphthalimide
analogues as potential inhibitors of both human MAO isoforms. The results document that 5-
sulfanylphthalimides are highly potent and selective MAO-B inhibitors with all of the examined
compounds possessing IC50 values in the nanomolar range. The most potent inhibitor, 5-
(benzylsulfanyl)phthalimide, exhibits an IC50 value of 0.0045 μM for the inhibition of MAO-B with
a 427–fold selectivity for MAO-B compared to MAO-A. We conclude that 5-sulfanylphthalimides
represent an interesting class of MAO-B inhibitors and may serve as lead compounds for the
design of antiparkinsonian therapy.
It has recently been reported that nitrile containing compounds frequently act as potent MAO-B
inhibitors. In an attempt to identify additional potent and selective inhibitors of MAO-B and to
contribute to the known structure-activity relationships of MAO inhibition by nitrile containing
compounds, the present study examined the MAO inhibitory properties of series of novel
sulfanylphthalonitriles and sulfanylbenzonitriles. The results document that the evaluated
compounds are potent and selective MAO-B inhibitors with most homologues possessing IC50
values in the nanomolar range. In general, the sulfanylphthalonitriles exhibited higher binding
affinities for MAO-B than the corresponding sulfanylbenzonitrile homologues. Among the
compounds evaluated, 4-[(4-bromobenzyl)sulfanyl]phthalonitrile is a particularly promising inhibitor since it displayed a high degree of selectivity (8720-fold) for MAO-B over MAO-A, and
potent MAO-B inhibition (IC50 = 0.025 μM). Based on these observations, this structure may
serve as a lead for the development of therapies for neurodegenerative disorders such as
Parkinson’s disease.
Adenosine A2A receptor antagonism -
Most adenosine A2A receptor antagonists belong to two different chemical classes, the xanthine
derivatives and the amino-substituted heterocyclic compounds. In an attempt to discover high
affinity A2A receptor antagonists for PD and to further explore the structure-activity relationships
of A2A antagonism by the xanthine class of compounds, this study examines the A2A
antagonistic properties of series of (E)-8-styrylxanthine, 8-(phenoxymethyl)xanthine and 8-(3-
phenylpropyl)xanthine derivatives. The results document that among these series, the (E)-8-
styrylxanthines are the most potent antagonists with the most potent homologue, (E)-1,3-dietyl-
7-methyl-8-[(3-trifluoromethyl)styryl]xanthine, exhibiting a Ki value of 11.9 nM. This compound
was also effective in reversing haloperidol-induced catalepsy in rats. The importance of
substitution at C8 with the styryl moiety was demonstrated by the finding that none of the 8-
(phenoxymethyl)xanthines and 8-(3-phenylpropyl)xanthines exhibited high binding affinities for
the A2A receptor. It was also concluded that (E)-8-styrylxanthines are potent A2A antagonists
with particularly the 1,3-dietyl-7-methylxanthine substitution pattern being most appropriate for
high affinity binding.
Conclusion -
The results of these studies have established that all of the sulfanylphthalimides,
sulfanylphthalonitriles and sulfanylbenzonitriles examined display significant MAO-B inhibitory
properties in vitro with IC50 values in the low μM to nM range. Good A2A receptor affinity was
demonstrated by the xanthines containing a styryl moiety, while the phenoxymethyl and
phenylpropyl xanthines exhibited poor activity.Thesis (PhD (Pharmaceutical Chemistry))--North-West University, Potchefstroom Campus, 2013
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Chiba, Diego Eidy. "Planejamento, síntese e avaliação biológica de novos derivados da série LAPDESF FTD-AO com potencial atividade no tratamento da Doença de Alzheimer /." Araraquara, 2019. http://hdl.handle.net/11449/183180.
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Orientador: Man Chin ChungResumo: A doença de Alzheimer (DA) é a principal e mais comum causa de demência senil, contribuindo com 50-75% dos casos diagnosticados. Nos países desenvolvidos, a DA é quarta causa de morte, ficando atrás somente de doenças cardiovasculares, câncer e acidente vascular cerebral. A projeção da Organização Mundial de Saúde (OMS) é que até 2050 o número de idosos aumente 21% no mundo. A DA é uma doença neurodegenerativa progressiva, na qual os pacientes diagnosticados mostram uma extensa perda de sinapses e neurônios no hipocampo e nos córtex frontal e temporal, comprometendo de forma gradual suas funções cognitivas, como a memória, capacidade de aprendizado, raciocínio, assim como o comprometimento da comunicação e habilidade realização de atividades diárias. Atualmente não há tratamento capaz de curar ou modificar de maneira eficaz a doença, apenas medicamentos (donepezila, rivastigmina, galantamina e memantina) que melhoram alguns sintomas manifestados pelos pacientes. A redução do processo de neuroinflamação e estresse oxidativo associados ao envelhecimento e aos marcadores da DA, como a formação de placas senis e emaranhados neurofibrilares, contribui na plasticidade sináptica, cognição e memória e atenuando os efeitos associados à perda de neurônios dos pacientes acometidos pela DA. Neste trabalho foram planejados e obtidos oito compostos intermediários e nove compostos finais inéditos, planejados através da estratégia de hibridização molecular do ácido lipóico ou ácido ferúlico ... (Resumo completo, clicar acesso eletrônico abaixo)
Abstract: Alzheimer's disease (AD) is the main and most common cause of senile dementia, accounting for 50-75% of diagnosed cases. In developed countries, AD is the fourth leading cause of death, leading only to cardiovascular disease, cancer and stroke. The projection of the World Health Organization (WHO) is that by 2050 the number of elderly people increase by 21% in the world. AD is a progressive neurodegenerative disease, in which the diagnosed patients show an extensive loss of synapses and neurons in the hippocampus and in the frontal and temporal cortex, gradually impairing their cognitive functions, such as memory, learning ability, reasoning, and communication impairment and ability to perform daily activities. Currently there is no treatment capable of curing or effectively modifying the disease, only medications (tacrine, donepezil, rivastigmine, galantamine and memantine) that improve some of the symptoms manifested by the patients. The reduction of neuroinflammation and oxidative stress associated with aging and AD markers, such as the formation of senile plaques and neurofibrillary tangles, contribute to synaptic plasticity, cognition and memory and attenuate the effects associated with the loss of neurons in patients with AD. In this work, eight intermediate compounds and nine unpublished final compounds were obtained through the molecular hybridization strategy of lipoic acid or ferulic acid with phthalimide derivatives. All compounds were chemically characterized by 1... (Complete abstract click electronic access below)
Doutor
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Ragunathan, Ramanaranjinie. "Studies of certain benzimidazoles, phthalazines and phthalimides." Thesis, Brunel University, 1991. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.292494.
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Romagnoli, Elia. "Iridium-catalyzed asymmetric hydrogenation of N-allyl phthalimides." Master's thesis, Alma Mater Studiorum - Università di Bologna, 2019. http://amslaurea.unibo.it/17959/.
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The unprecedented iridium-catalyzed asymmetric hydrogenation of N-allyl phthalimides to afford enantioenriched chiral amines bearing a β-methyl is presented. Recently developed Ir-MaxPHOX are used as catalysts for this enantioselective transformation. The hydrogenation reaction has been studied in detail in order to find the optimal conditions. The mild reaction conditions and the feasibility of the removal of the phthalimido protecting group makes this process easily scalable and of interest for multiple synthetic applications.
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Habib, Osama Mahmoud Ali [Verfasser]. "Tricarbonylchrom(O)-Komplexe von Phthalimids Derivaten / Osama Mahmoud Ali Habib." Hannover : Technische Informationsbibliothek und Universitätsbibliothek Hannover, 2010. http://d-nb.info/1004016247/34.
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Oelgemöller, Michael. "Photochemie von Phthalimiden photodecarboxylative Addition von Carboxylaten und PET-induzierte Makrocyclisierungen /." [S.l. : s.n.], 1999. http://deposit.ddb.de/cgi-bin/dokserv?idn=95974973X.
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Zhang, Yu-Feng. "Selective Electrocatalytic reduction mediated by Sm(II) : Application to nitroarenes, sulfoxides and phthalimides." Thesis, Université Paris-Saclay (ComUE), 2017. http://www.theses.fr/2017SACLS596/document.
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Le SmI₂ en tant que réactif de transfert monoélectronique a été largement utilisé en chimie organique depuis les premiers travaux de Kagan. Cependant, la quantité stœchiométrique ou en excès de SmI₂ et d'additifs toxique tels que HMPA sont utilisés normalement pour améliorer la réactivité. De plus, à cause de sa sensibilité à l'oxygène, le stockage de la solution de SmI₂ dans le THF est difficile. Récemment, nous avons développé une nouvelle méthode électrocatalytique basée sur la régénération électrochimique de Sm²⁺. Par rapport à la réactivité du SmI₂ classique, notre approche utilise une quantité catalytique de Sm. Premièrement, pour la réduction de nitroarènes, la réaction a sélectivement fourni les composés aromatiques azoïques et les anilines en fonction du solvant choisi. Notamment, c'est la première fois que la réaction Sm²⁺ se produit dans le méthanol dans le cas des anilines. Deuxièmement, dans le cas de la réduction des sulfoxydes par SmI₂, en général, l'HMPA était nécessaire comme additif. Dans notre procédé électrocatalytique, les sulfoxydes ont été transformés en sulfures avec une chimiosélectivité élevée et des excellents rendements toujours à température ambiante sans besoin ni de HMPA ni d’atmosphère protectrice. Enfin, les dérivés d'isoindolinone sont des séries de produits importants en chimie organique, la réduction des phtalimides est l'approche la plus pratique pour les obtenir. Avec les alcools, l'alcoxylation réductrice de phtalimides a eu lieu pour la première fois avec le Sm²⁺ électrocatalytique dans nos conditions. Et si on ajoute d'autres sources de protons, ce procédé a fourni les ω-hydroxylactames et isoindolinones correspondants avec des rendements élevésThe SmI₂ as a single electron transfer reagent has been widely used in organic chemistry since the pioneering works by Kagan. However, the stoichiometric or excess amount of SmI₂ and harmful additives such as HMPA are used normally to enhance the reactivity, moreover, due to the oxygen sensitive, the storage of SmI₂ solution is difficult.Recently, we have developed a new electrocatalytic method based on the electrochemical regeneration of Sm²⁺. Compared to the classic SmI₂ reaction, our process occurred with a catalytic amount of Sm. In the reduction of nitroarenes, it selectively afforded the azo aromatic compounds and anilines depending on different solvents system. Notably, it’s the first time that the Sm²⁺ reaction occurred in the methanol. Normally, the HMPA was the additive in the reduction of sulfoxides by SmI₂. Under our electrocatalytic process, the sulfoxides were converted into sulfides in high chemoselectivity and yield at room temperature without HMPA and protecting atmosphere.The isoindolinone derivatives are series of important products in organic chemistry, the reduction of phthalimides is the most convenient approach to provide them. With alcohols, the unprecedented Sm²⁺ electrocatalyzed reductive alkoxylation of phthalimides was established. Moreover, adding other proton sources, this process afforded the corresponding ω-hydroxylactams and isoindolinones
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Hanft, Sebastian [Verfasser]. "Phthalimid-Harnstoff-Konjugate als Fluoreszenzsensoren und chirale Template für [4+4]-Cycloadditionen / Sebastian Hanft." München : Verlag Dr. Hut, 2014. http://d-nb.info/1060587572/34.
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Schulze, Wolfram [Verfasser]. "Synthese von Benzopyrrolizidinonderivaten durch intramolekulare Photodecarboxylierung und Studien zu Photodecarboxylierungen mit substituierten Phthalimiden / Wolfram Schulze." München : Verlag Dr. Hut, 2019. http://d-nb.info/1186453699/34.
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Reiffers, Anna [Verfasser], Peter [Gutachter] Gilch, and Axel [Gutachter] Griesbeck. "Zeitaufgelöste Spektroskopie zur Photophysik und Photochemie von Phthalimiden / Anna Reiffers ; Gutachter: Peter Gilch, Axel Griesbeck." Düsseldorf : Universitäts- und Landesbibliothek der Heinrich-Heine-Universität Düsseldorf, 2021. http://d-nb.info/1228147574/34.
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Heinrich, Thomas. "Photo-Elektronen-Transfer-induzierte Reaktionen von Phthalimiden, Succin- und Maleimiden Synthesen von Pyrrolizidinen und cyclischen Peptiden /." [S.l. : s.n.], 2002. http://deposit.ddb.de/cgi-bin/dokserv?idn=964919745.
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Vollmer, Moritz [Verfasser]. "Neue hocheffiziente Phthalimid- und Naphthalimid-basierte Fluoreszenzfarbstoffe: Synthese, photophysikalische Charakterisierung und Einsatz als optische Aufheller / Moritz Vollmer." München : Verlag Dr. Hut, 2019. http://d-nb.info/1198542691/34.
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Patil, Shradha Vasant. "Radical additions of hydrocarbons, ethers and acetals to alkenes via allyl transfer reaction: A new chain reaction for C-H bond functionalization." Diss., Virginia Tech, 2013. http://hdl.handle.net/10919/50658.
Full textAbstract:
Functionalization of hydrocarbons via a free-radical based allyl transfer reaction using various allyl bromide substrates has been previously studied. The work described in this dissertation focuses on the replacement of Br by phthalimido-N-oxyl (PINO ) which helps make this chemistry environmentally friendly. To replace Br with PINO , replacement of previously used allyl-bromide substrates with new allyl-PINO substrates were necessary. Various allyl- PINO compounds were synthesized and the use of these allyl-phthalimido-N-oxyl (allyl-PINO) compounds for the functionalization of various alkyl aromatic hydrocarbons is demonstrated.Kinetic studies were performed to observe the efficiency of the new chain reaction compared to the previously reported studies with allyl-bromides. We recently discovered that these allyl substrates are useful for the functionalization of ethers and acetals. The functionalization of various cyclic and acyclic ethers was performed using these allyl transfer reactions. This reaction was also performed in-solution, which allowed us to perform these reactions at low reagent concentrations. Kinetic chain lengths were measured for these reactions. High chain lengths were observed for all used ethers. Kinetic studies to investigate the rate of radical addition-elimination processes were performed using laser flash photolysis and competition kinetics. These experiments helped us to measure the reactivity and selectivity of PINO as a chain carrier in comparison with Br .
Additionally, a new competition experiment was designed to study the relative rate constant for
the -fragmentation process. For this experiment a novel substrate that contains two leaving
groups, Br and PINO , was synthesized, and the relative rates of elimination of Br vs PINO
were compared.
Ph. D.
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Öngel, Banu [Verfasser]. "Neuartige Photoschalter auf Basis von Phthalimid-basierten Azobenzolen und Chalkonen: Synthese und photophysikalische Untersuchung der reversiblen E/Z-Isomerisierung / Banu Öngel." München : Verlag Dr. Hut, 2020. http://d-nb.info/1220567590/34.
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ALIANÇA, Amanda Silva dos Santos. "Atividade biológico de compostos ftalimido-Tiazóis sobre Leishmania infantum (Nicolle, 1908)." Universidade Federal de Pernambuco, 2016. https://repositorio.ufpe.br/handle/123456789/17557.
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CAPEs
A leishmaniose é uma doença infecciosa, não contagiosa de caráter zoonótico, causada por vários tipos de protozoários do gênero Leishmania. Em humanos, a doença apresenta três principais formas clínicas, dependendo das espécies envolvidas de Leishmania: a cutânea, mucocutânea e visceral (LV), sendo esta última a forma mais grave que quando não tratada pode evoluir para óbito em mais de 90% dos casos. O agente etiológico da LV compreende Leishmania donovani na Índia e leste da África; Leishmania infantum na China, Ásia central, Europa, África, América do Sul e Central. Calcula-se que a prevalência mundial de leishmaniose esteja em torno de 12 milhões de pessoas, acometendo 80 países e com uma estimativa de 400.000 novos casos da doença por ano. O tratamento atual para a leishmaniose é baseado na utilização de antimoniais pentavalentes como o estibogluconato de sódio (Pentostan®) e o antimoniato de meglumina (Glucantime®), este apresenta várias dificuldades como toxicidade, via de administração intravenosa e tempo prolongado de tratamento, que levam a sua descontinuação. Diante deste cenário, os compostos sintéticos são de grande importância na terapêutica por representarem 85% dos fármacos disponíveis. As ftalimidas e os tiazóis são importantes classes de compostos sintéticos e apresentam amplo espectro de atividades biológicas, como ansiolítica, anti-Parkinson, anti-Alzheimer, analgésica, anti-inflamatória, imunomoduladora e antibacteriana. O presente trabalho teve como objetivo avaliar a atividade in vitro frente a L. infantum e a células de mamíferos de uma série de 15 derivados ftalimido-tiazóis. Os compostos foram avaliados frente a formas promastigotas e amastigotas de L. infantum, quanto à citotoxicidade frente a células vero, macrófagos J774 e macrófagos peritoneais, a produção de óxido nítrico e alterações sobre alvos intracelulares do parasito. Os resultados mostram que os compostos oriundos da hibridação da ftalimida com 1,3 tiazol apresentaram atividade leishmanicida contra formas promastigota de L. infantum, baixa citotoxicidade às células de mamíferos testadas e aumentaram a produção de ON em relação às células controles nos macrófagos não infectados. Os compostos 2j e 2m se mostraram como os mais potentes contra as formas promastigotas da série testada, estes foram testados frente as formas amastigotas, os compostos reduziram a sobrevivência de amastigotas intracelulares e apresentaram baixa citotoxicidade para os macrófagos peritoneais. Formas promastigotas tratadas com esses compostos apresentaram alterações ultraestruturais como: encolhimento do corpo celular, perda da integridade da membrana celular, vacuolização do citoplasma, perfis de membranas circundando organelas e inchaço da mitocôndria. Quando avaliada a marcação pelo iodeto de propídio e pela rodamina 123, formas promastigotas tratadas com os compostos 2j e 2m apresentaram aumento no número de células marcadas com o iodeto de propídio e induziram alterações significativas no potencial de membrana mitocondrial. Dessa maneira, os compostos ftalimido-tiazóis apresentam atividades leishmanicida e devem formar a base para futuros estudos experimentais.
Leishmaniasis is an infectious disease, non-contagious with zoonotic characteristic, caused by several types of protozoa of the genus Leishmania. In humans, the disease has three main clinical forms, depending on the species of Leishmania involved: cutaneous, mucocutaneous and visceral, the latter being the more severe if left untreated can lead to death in more than 90% of cases. The etiologic agent of LV comprises Leishmania donovani in India and East Africa; Leishmania infantum in China, Central Asia, Europe, Africa, South and Central America. It is estimated that the worldwide prevalence of leishmaniasis is around 12 million people in 80 countries and 400,000 new cases per year. The current treatment for leishmaniasis is based on the use of pentavalent antimonials such as stibogluconate sodium (Pentostan®) and meglumine antimonate (Glucantime®), this presents several problems such as difficulties such as toxicity, intravenous route of administration and prolonged treatment, which leads to its discontinuation of the treatment. The phthalimides and thiazoles are important classes of synthetic compounds and have a broad spectrum of biological activities such as anxiolytic, anti-Parkinsons, anti-Alzheimer, analgesic, antiinflammatory, immunomodulating and antibacterial. This study aimed to evaluate the in vitro activity against L. infantum and mammalian cells in a series of 15-phthalimido thiazoles derivatives. The present work report the in vitro activity of a phthalimido-thiazoles derivatives series. The activities were evaluated against promastigotes and amastigotes of Leishmania infantum, front of cytotoxicity to vero cells, J774 macrophages and peritoneal macrophages, the effect on production of nitric oxide (NO) and changes of intracellular targets on the parasite. The results show that the compounds arising from the hybridization of phthalimido 1, 3 thiazole showed leishmanicidal activity against promastigotes forms of L. infantum, low cytotoxicity to mammalian cells and increased the NO production compared to control cells in uninfected macrophages. The compounds 2j and 2m are shown as the most potent against promastigotes of the test series, these were tested against amastigote forms, the compounds reduced the survival of intracellular amastigotes and showed low cytotoxicity peritoneal macrophages. The promastigotes treated with these compounds exhibited ultrastructural changes such as cell body shrinkage, loss of cell membrane integrity, vacuolization of the cytoplasm membranes surrounding organelles profiles and swelling of mitochondria. The compounds 2j and 2m were the most potent of the series tested and the parasites treated with these compounds showed ultrastructural changes such as cell body shrinkage, loss of cellular membrane integrity, vacuolization of cytoplasm, membrane profiles surrounding organelles and swelling of mitochondria. When assessed by propidium iodide tag and the rhodamine 123 promastigotes treated with the compounds 2j and 2m showed an increase in the number of cells stained with propidium iodide and induced significant changes in mitochondrial membrane potential. Thus, the phthalimido-thiazoles compounds have leishmanicide activities and should form the basis for future experimental studies.
22
Vanel, Rémi. "Conception de catalyseurs d'oxydation non métalliques utilisant l'oxygène de l'air." Thesis, Grenoble, 2011. http://www.theses.fr/2011GRENV058/document.
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Le N-hydroxytétraphénylphtalimide (NHTPPI) présente une activité catalytique sensiblement supérieure à celle du N-hydroxyphtalimide (NHPI) dans l'oxydation aérobie de substrats organiques. Deux nouvelles voies d'accès à des analogues fonctionnalisés du NHTPPI ont été étudiées. La première implique une réaction de Diels-Alder entre des oxydes ou dioxydes de thiophènes polyaromatiques et le maléimide ou l'anhydride maléique. De nombreuses limitations rendent cette approche difficilement généralisable. Dans la deuxième voie, l'étape clé est une cycloaddition entre des tétracyclones ou des acécyclones et le 2-bromomaléimide qui conduit directement au motif phtalimide par décarbonylation et déshydrobromation de l'adduit de Diels-Alder. Cette méthodologie de synthèse très efficace et tolérante a permis d'introduire des groupements variés sur les cycles aromatiques portés par le noyau benzénique central et d'obtenir de nouveaux analogues du NHTPPI ainsi que des N-hydroxydiarylacénaphtophtalimides en seulement trois à cinq étapes. La chiralité axiale a été mise en évidence en série diarylacénaphtophtalimide et la séparation d'énantiomères a été réalisée dans un premier cas, ce qui ouvre la voie vers de nouveaux analogues chiraux du NHPI. Les nouveaux N-hydroxyimides obtenus ont montré d'excellentes performances en catalyse d'oxydation aérobie, dans tous les cas supérieurs à celles du NHPI et, dans certains cas, à celles du NHTPPIN-Hydroxytetraphenylphthalimide (NHTPPI) exhibits a better catalytic activity than N-hydroxyphtalimide (NHPI) in the aerobic oxidation of organic substrates. Two new routes to functionalized analogs of NHTPPI have been studied. The first one involves a Diels-Alder reaction between polyaromatic thiophene oxides or dioxides and maleimide or maleic anhydrid. Several limitations make this approach difficult to generalize. In the second approach, the key step is a cycloaddition between tetracyclones or acecyclones and 2-bromomaleimide to directly give the phthalimide framework by decarbonylation and deshydrobromation of the Diels-Alder adduct. This versatile and efficient methodology allowed us to introduce various functional groups on the aromatic cycles borne by the central ring, and thus, new NHTPPI analogs, along with N-hydroxydiarylacenaphthophtalimides, were obtained in only three to five steps. Axial chirality was underlined in the diarylacenaphtophtalimide family and resolution of enantiomers was carried out in one case, which opens a way to new chiral analogs of NHPI. The new N-hydroxyimides exhibit excellent performances as catalysts in aerobic oxidation, superior to NHPI and, in some cases, to NHTPPI
23
Peng, Kai-En, and 彭愷恩. "Introduction of NHC Moiety to Primary Amines Through Phthalimide Linkage." Thesis, 2016. http://ndltd.ncl.edu.tw/handle/81049513925345191202.
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碩士國立臺灣大學
化學研究所
104
N-heterocyclic carbenes (NHCs) have been widely studied recent years. However, the synthesis of NHC could sometimes be complicated, especially when non-chelating symmetrical poly-functional carbene ligands are anticipated. Therefore, we decided to develop a simple method to introduce NHC unit to various molecular backbones using a sole NHC precursor. In this research, a LEGO brick bifunctional ligand, which bears an imidazole moiety on one side of the molecule and phthalic anhydride functionality on the other side, was synthesized. While the imidazole part represents the NHC precursor, the phthalic anhydride group reacts with primary amine containing molecule to introduce the NHC moiety via phthalimide linkage. With this synthetic protocol, poly NHCs and the corresponding poly-nuclear nickel complexes with 1-D, 2-D, and 3-D molecular structure were synthesized. Catalytic performances of these poly-Ni complexes illustrated the negligible interactions between the nickel centers. Furthermore, the synthetic protocol was found to be applicable to various amino acids to give the amino acid tethered benzimidazolium salts and the corresponding metal complexes. The combination of amino acid and NHC ligand is anticipated to improve the bio-compatibility of NHC-metal complexes for selective drug delivery.
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Chang, Chiachen, and 張嘉臻. "Study on the synthesis and photoluminescence of tetra-phenyl or biphenyl N-substitute phthalimide." Thesis, 2012. http://ndltd.ncl.edu.tw/handle/94696744249076380310.
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碩士國立暨南國際大學
應用化學系
100
New aggregation induced emission materials have a wide range of applications and have been confirmed, but the AIE type of material has been published is still scarce. The material of pure organic compounds are particularly rare. Therefore, in this thesis, we have developed a series of new luminescent materials with AIE nature, that is tetra-phenyl or biphenyl N-substitute phthalimide, and used the simple route to do the synthesis. We also measure the fluorescence properties of the synthesized phthalimide compounds containing aromatic group, with the measure containing the absorption spectrum, emission spectrum and quantum yield. We also have compared the fluorescence properties in different substitute, containing various kinds of aromatic ring and the different functional groups. In this thesis, we try to explore the impact on the compounds properties in the polar and nonpolar solvents.
25
Wieghaus, Kristen Anne. "Phthalimide neovascular factor 1 (PNF1) for therapeutic neovascularization : an investigation of mechanism and controlled release /." 2008. http://wwwlib.umi.com/dissertations/fullcit/3312107.
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Huang, Tzu-Ping, and 黃梓萍. "Study on the Synthesis and Photoluminescence of Tetra-trifluoromethylphenyl or Tetra-thiophenyl N-Substituted Phthalimide." Thesis, 2013. http://ndltd.ncl.edu.tw/handle/68390198208886025270.
Full textAbstract:
碩士國立暨南國際大學
應用化學系
101
In this study, we designed and successful to synthesized two series of tetra – trifluoromethylphenyl or thiophenyl N – substituted phthalimides, and investigated there organic molecular characters and measured the UV – Vis and photoluminescence of this two series compounds in various ratio of ethanol / dichloromethane mixture. However, the experimental results showed that while the electron – donating units, like butyl, toluene, …… etc. functional groups of N – substituted phthalimide, the maximum quantum yield (Q.Y.) almost at the ethanol content of 0 %, and exhibited very low fluorescent (< 2 %) , and while the electron – accepting units, like benzylacetyl、 benzylnitrile etc. functional groups of N – substituted phthalimide, we could not get the compound that we expected. As the series of thiophenyl N – substituted pthalimide, although the maximum Quantum yield almost at the ethanol content of 60 – 90 % while the electron – donating units, like butyl, toluene, ……etc. functional groups of N – substituted phthalimide, the photoluminescence intensity were too weak (< 8 %). As well as the electron – accepting units, like benzylacetyl、 benzylnitrile etc. functional groups of N – substituted pthalimide, the yield of theses were too low to detect the photoluminescence, and the yield were 3.8 and 3.9 %, respectively. Thus, in this work, we have discussed against the two series of varies functional of compounds.
27
Díaz, Pérez Yrene Hortencia [Verfasser]. "New Phthalimide-based sensors for chiral and achiral anions and peroxides / vorgelegt von Yrene Hortencia Díaz Pérez." 2009. http://d-nb.info/1008304972/34.
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Zhao-Karger, Zhirong [Verfasser]. "The first anionic thia-Fries rearrangement at arene tricarbonylchromium complexes and reactions of phthalimide tricarbonylchromium complexes / von Zhirong Zhao-Karger." 2006. http://d-nb.info/983769435/34.
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Oelgemöller, Michael. "Photochemie von phthalimiden: photodecarboxylative addition von carboxylaten und PET–induzierte makrocyclisierungen." Thesis, 1999. http://kups.ub.uni-koeln.de/566/.
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[Extract] This PhD thesis describes the development of photodecarboxylative additions to phthalimides as a green alternative to Grignard reactions and photoinduced electron transfer cyclizations to macrocyclic products.
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Chen, Tsung-Ho, and 陳宗禾. "Polyphenylene Linked Multi-functional Phthalimides : Synthesis, Solid-State Structures, and Ring-Opening Metathesis Polymerization." Thesis, 2005. http://ndltd.ncl.edu.tw/handle/81319642172572533827.
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碩士國立中正大學
化學所
93
The anhydride 26 used as starting material was made from 2,3-dicyanohydroquinone via a series of treatments, such as oxidation, Diels-Alder cycloaddition, enolization, methylation, basic hydrolysis, and acidic dehydration. The condensations of anhydride 26 with conjugated amines were successfully achieved under specific concentration or equivalent conditions to give both [1+1] and [2+1] imide products. The conformational isomers of imide 40, 41, 44 were also detected in our characterizations. In dynamic NMR studies, the interconversions of the conformational isomers of each compound were obviously observed, because the increasing temperature technique overcame the steric hindrance of single bond rotations. The phenomena shown in NMR spectra provided us reasonable evidences for the isomers we found. Except compounds 40, 41, and 44 , we found that there exists enantiomers in equal ratio inside each unit cell, in the X-ray diffraction characterization for each imide product. In the solid-state structural analysis of each diimide compound, we observed the methylenes on the bridges were trans to one another, and the isoindole planes of either sides of the imide molecules were coplanar with one another. By these the crystalline packing pattern shown, we may estimate that the observed conformations of imides correspond to most steady energetic requirements for crystalline packings. Imide 37, 38, 40, and 45, were also reacted with ruthenium carbene catalyst to undergo ring-opening metathesis polymerization (ROMP) in our researches. The polymerization feature of the four polymers obtained was also analyzed to give respective PDI value. All of the PDI values are lower than 1.4, these ROMP was classified as typical active polymerization.
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Oelgemöller, Michael [Verfasser]. "Photochemie von Phthalimiden : photodecarboxylative Addition von Carboxylaten und PET-induzierte Makrocyclisierungen / vorgelegt von Michael Oelgemöller." 1999. http://d-nb.info/95974973X/34.
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Lee, Hsin-Jie, and 李欣潔. "Study on the synthesis and photoluminescence of the tetra (1-naphthyl) phenyl N-substituted phthalimides." Thesis, 2013. http://ndltd.ncl.edu.tw/handle/42715196092252847605.
Full textAbstract:
碩士國立暨南國際大學
應用化學系
102
Organic light-emitting materials have attracted considerable interest for recent years. In particular, aggregation induced emission (AIE) material have been focus of many recent studies, especially the effect of structural changes in organic light-emitting material. In this thesis, we introduce the AIE mechanism in detail. Based on the mechanistic understanding, we developed a series of new aggregation-induced emission compounds such as tetra (1-naphthyl) phenyl N-substituted phthalicamindes, which contain different substituents. Then, we explore the AIE effect of these compounds by measurement of fluorescence properties, absorption spectrum, emission spectrum and quantum yield. And we explore the solvent effect of these compounds.
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Heinrich, Thomas [Verfasser]. "Photo-Elektronen-Transfer-induzierte Reaktionen von Phthalimiden, Succin- und Maleimiden : Synthesen von Pyrrolizidinen und cyclischen Peptiden / vorgelegt von Thomas Heinrich." 2002. http://d-nb.info/964919745/34.
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WANG, YI-FU, and 王億富. "液相層析用衍生試劑2'-(N-Phthalimido)ethyl2-(N,N-dimethylamino)ethanesulfonate之合成及應用研究." Thesis, 1993. http://ndltd.ncl.edu.tw/handle/60450176728012131334.
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Φυτίλης, Ιωάννης. "Διφωτονική απορρόφηση νέων συμμετρικών οργανικών ενώσεων και διφωτονικός πολυμερισμός." Thesis, 2009. http://nemertes.lis.upatras.gr/jspui/handle/10889/2784.
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Η διφωτονική απορρόφηση (ΔΦΑ) είναι το μη γραμμικό-φαινόμενο κατά το
οποίο δύο φωτόνια απορροφούνται ταυτόχρονα σε ένα υλικό μέσο. Τα τελευταία 20
χρόνια το φαινόμενο αυτό έχει προσελκύσει ιδιαίτερα το ενδιαφέρον της
επιστημονικής κοινότητας για την ανακάλυψη νέων αποδοτικών ενώσεων λόγω και
των εφαρμογών που έχει βρεθεί ότι μπορεί να προσφέρει. Η διφωτονική
μικροσκοπία, ο διφωτονικός πολυμερισμός, η τρισδιάστατη αποθήκευση δεδομένων
είναι μερικές από τις σημαντικές εφαρμογές που εκμεταλλεύονται τα πλεονεκτήματα
της ΔΦΑ. Τη τελευταία δεκαετία η έρευνα επικεντρώνεται στη θεωρητική και
πειραματική μελέτη της ΔΦΑ οργανικών ενώσεων με σκοπό την διασύνδεσης των
χαρακτηριστικών της δομής των μορίων με την ΔΦΑ που παρέχουν και την εύρεση
στρατηγικών σύνθεσης οργανικών ενώσεων υψηλής ΔΦΑ. Επίσης πολλές είναι οι
επιστημονικές εργασίες που χρησιμοποιούν τις ενώσεις αυτές στην έρευνα για την
ανάπτυξη και βελτίωση των διφωτονικών εφαρμογών.
Στη διατριβή αυτή γίνεται μελέτη της ΔΦΑ συζυγιακών οργανικών ενώσεων
αποτελούμενες από ένα κεντρικό τμήμα συνδεδεμένο αντιδιαμετρικά με δυο ίδιους
υποκαταστάτες. Τα συμμετρικά αυτά μόρια έχουν ως κεντρικό τμήμα φλουορένιο ή
αλκόξυ-φαινυλένιο ή καρβοξύλιο και διάφορους υποκαταστάτες στα άκρα. Η τεχνική
μέτρησης διφωτονικά διεγερμένου φθορισμού με laser femtosecond χρησιμοποιήθηκε
για τον υπολογισμό των τιμών της ενεργούς διατομής ΔΦΑ των μορίων στη
φασματική περιοχή 750-840nm. Από τη συγκριτική μελέτη των ενώσεων προκύπτει
ότι ο υποκαταστάτης φθαλιμίδιο προσφέρει την μεγαλύτερη ΔΦΑ και για τα τρία
διαφορετικά κεντρικά τμήματα, ενώ όταν συνδέεται με το φλουορένιο έχει την
υψηλότερη ενεργό διατομή ΔΦΑ φθάνοντας την τιμή των 1650GM στη φασματική
περιοχή που μελετήθηκε. Επίσης παρατηρήθηκε ότι ο υποκαταστάτης ναφθαλιμίδιο
προκαλεί μετατόπιση του μεγίστου ΔΦΑ σε αρκετά μεγαλύτερα μήκη κύματος.
Παρόμοια μετατόπιση παρατηρείται και για τα μόρια με κεντρικό τμήμα το
καρβαζόλιο. Η μετατόπιση αυτή του φάσματος ΔΦΑ δεν αντιστοιχεί σε μετατόπιση
του φάσματος μονοφωτονικής απορρόφησης. Οφείλεται στην άρση της
κεντροσυμμετρίας του μορίου, λόγω της διαμόρφωσης της δομής του, η οποία κάνει
επιτρεπτή τη διφωτονική μετάβαση στην πρώτη μονοφωτονικά επιτρεπτή ενεργειακή
κατάσταση που ειδάλλως είναι απαγορευμένη.
Η επίδραση του διαλύτη στις διφωτονικές ιδιότητες των μορίων μελετάται
επίσης στη διατριβή αυτή. Για τις τέσσερις πιο αποδοτικές ενώσεις, ως προς το
διφωτονικά διεγερμένο φθορισμό, έγιναν μετρήσεις για τον υπολογισμό των
φασμάτων ΔΦΑ τους σε πέντε διαλύτες διαφορετικής πολικότητας (διηλεκτρικής
σταθεράς). Από τις μετρήσεις φάνηκε η σημαντική επίδραση του διαλύτη στη ΔΦΑ
των τεσσάρων χρωστικών η οποία μεγιστοποιείται σε διαλύτη μεσαίας πολικότητας,
ο τρεις στην ακετοφαινόνη και μια στο THF. Η χαμηλή κβαντική απόδοση
φθορισμού που παρατηρείται στα διαλύματα με ακετοφαινόνης μειώνει αρκετά το
διφωτονικά προκαλούμενο φθορισμό και κατατάσσει τo THF ως τον αποδοτικότερο
διαλύτη για διφωτονικές εφαρμογές που εκμεταλλεύονται το φθορισμό. Επίσης και ο
μη πολικός διαλύτης τολουόλιο προκαλεί έντονο φθορισμό λόγω της υψηλής
κβαντικής απόδοσης παρόλο που επιφέρει δραστική μείωση της ΔΦΑ σε σύγκριση με
τους άλλους διαλύτες που μελετήθηκαν.
Δύο από τις χρωστικές που μελετήθηκαν ως προς τη ΔΦΑ τους
χρησιμοποιήθηκαν ως φωτοεκκινητής πολυμερισμού ενός ακρυλικού μονομερούς και
την μελέτη του πολυμερισμού συναρτήσει διαφόρων παραμέτρων ακτινοβόλησης της
ρητίνης. Οι χρωστικές αυτές έχουν φλουορένιο ως κεντρικό τμήμα και
υποκαταστάτες στα άκρα φθαλιμίδιο ή τριφαινυλαμίνη. Και οι δύο χρωστικές δύναται
να προκαλέσουν τον πολυμερισμό του μονομερούς με ακτινοβόληση υπερβραχέων
παλμών στα 800nm, αλλά η προσθήκη αμίνης ως συνεκκινητή μειώνει το κατώφλι
ισχύος εκκίνησης του. Επίσης, σε υψηλές τιμές ισχύος ακτινοβόλησης στο ίδιο μήκος
κύματος παρατηρήθηκε αυτο-πολυμερισμός του μονομερούς γεγονός το οποίο έχει
επισημανθεί μία μόνο ακόμη φορά σε μια εργασία με ρητίνη μίξης τριών ακρυλικών
μονομερών.
Δύο ρητίνες που παρασκευάστηκαν στην παρούσα διατριβή αναμιγνύοντας το
μονομερές με τη κάθε χρωστική και με προσθήκη του συνεκκινητή μελετήθηκαν για
την εξάρτηση του πολυμερισμού από τον φακό εστίασης και από την ισχύ, την
ταχύτητα σάρωσης και τη διάμετρο της δέσμης. Για το σκοπό αυτό κατασκευάστηκαν
δοκίμια στα οποία εγγράφονταν πολυμερισμένες γραμμές μεταβάλλοντας κάποια από
τις παραπάνω παραμέτρους και μετρώντας το πάχος και το ύψος των γραμμών αυτών
από τις εικόνες μικροσκοπίου σάρωσης ηλεκτρονίων. Το γεγονός ότι ο μικρότερης
ισχύος φακός παρατηρηθηκε ότι προκαλεί λεπτότερη γραμμή εξηγείται από το
φαινόμενο κατωφλίου του πολυμερισμού. Ωστόσο η λεπτότερη γραμμή
επιτυγχάνεται με τον ισχυρότερο φακό καθώς μπορεί να μειωθεί περισσότερο η ισχύς
της δέσμης λόγω του χαμηλότερου κατωφλίου εκκίνησης του πολυμερισμού για το
φακό αυτό. Η αύξηση της ταχύτητας σάρωσης ή η μείωση της ισχύος της δέσμης
επιφέρουν μικρότερες διαστάσεις πάχους και ύψους της γραμμής που πολυμερίζεται.
Επίσης η κατανομή της ισχύος ακτινοβόλησης σε ολόκληρο το πίσω άνοιγμα του
φακού επιφέρει καλύτερη εστίαση και λεπτότερη πολυμερισμένη γραμμή. Ωστόσο η
κατάλληλη χωρική διαμόρφωση της δέσμης μπορεί να μειώσει τις διαστάσεις των
πολυμερισμένων δομών.-