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Journal articles on the topic 'Thiophene derivatives'

Author: Grafiati

Published: 4 June 2021

Last updated: 26 July 2025

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1

Clark, Peter D., Nicholas M. Irvine, and Pratibha Sarkar. "The synthesis of 3H-naphthol[1,8-bc]thiophene derivatives." Canadian Journal of Chemistry 69, no. 6 (1991): 1011–16. http://dx.doi.org/10.1139/v91-148.

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Methods for the synthesis of keto derivatives of the little studied naphtho[1,8-bc]thiophene system have been developed. Using the readily available benzothiophene derivative 6,7-dihydrobenzo[b]thiophen-4(5H)-one 4, a 3-keto-naphtho[1,8-bc]thiophene 14 was synthesized by a tin(IV) chloride catalyzed cyclization of the acid chloride derivative of the saturated acid 13b. The bicyclic ketone 4 was also used to prepare the keto-sulfoxide 7, which was cyclized to the 4-keto-naphtho[1,8-bc]thiophene system 9 in a Pummerer-type rearrangement. Key words: synthesis, organosulfur, naphtho[1,8-bc]thiophe

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2

Duc, Dau Xuan. "Recent Progress in the Synthesis of Benzo[b]thiophene." Current Organic Chemistry 24, no. 19 (2020): 2256–71. http://dx.doi.org/10.2174/1385272824999200820151545.

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: Benzo[b]thiophenes are aromatic heterocyclic compounds containing benzene and thiophene rings. This class of heterocycles is present in a large number of natural and non-natural compounds. Benzo[b]thiophene derivatives have a broad range of applications in medicinal chemistry such as antimicrobial, anticancer, antioxidant, anti-HIV and antiinflammatory activities. The use of benzo[b]thiophene derivatives in other fields has also been reported. Various benzo[b]thiophenes compounds have been employed as organic photoelectric materials, while several benzo[b]thiophenes have been used as organic

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3

Vu Quoc, Trung, Duong Tran Thi Thuy, Thuan Dang Thanh, et al. "Some chalcones derived from thiophene-3-carbaldehyde: synthesis and crystal structures." Acta Crystallographica Section E Crystallographic Communications 75, no. 7 (2019): 957–63. http://dx.doi.org/10.1107/s2056989019007503.

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The synthesis, spectroscopic data and crystal and molecular structures of four 3-(3-phenylprop-1-ene-3-one-1-yl)thiophene derivatives, namely 1-(4-hydroxyphenyl)-3-(thiophen-3-yl)prop-1-en-3-one, C13H10O2S, (1), 1-(4-methoxyphenyl)-3-(thiophen-3-yl)prop-1-en-3-one, C14H12O2S, (2), 1-(4-ethoxyphenyl)-3-(thiophen-3-yl)prop-1-en-3-one, C15H14O2S, (3), and 1-(4-bromophenyl)-3-(thiophen-3-yl)prop-1-en-3-one, C13H9BrOS, (4), are described. The four chalcones have been synthesized by reaction of thiophene-3-carbaldehyde with an acetophenone derivative in an absolute ethanol solution containing potass

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4

Sikha, Lahiri, and K. Sen P. "Cyclohepta[b]thiophene derivatives. Part-IV. Dehydrogenation of cyclohepta[b]thiophene and cyclohepta[c]thiophene derivatives." Journal of Indian Chemical Society Vol. 76, Apr 1999 (1999): 209–12. https://doi.org/10.5281/zenodo.5848369.

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Department of Chemistry, Presidency College, Calcutta-700 073, India <em>Manuscript received 23 March 1998, revised 26 October 1998, accepted 16 December 1998</em> Cyclohepta[<em>b</em>]thiophenes 3 and cyclohepta[<em>c</em>]thiophene 4 on dehydrogenation with selenium give a complex mixture of dehydrogenated products. The formation of the identified products is explained through the initial homolytic cleavage at more than one particular bond in the cycloheptane moiety of 3 and 4. In all these cases ring contraction of the seven-membered ring of the thiophenes 3 and 4 is observed.

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5

Arrousse, N., Y. Fernine, Nabil Al-Zaqri, et al. "Thiophene derivatives as corrosion inhibitors for 2024-T3 aluminum alloy in hydrochloric acid medium." RSC Advances 12, no. 17 (2022): 10321–35. http://dx.doi.org/10.1039/d2ra00185c.

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Thiophene derivatives: thiophene-2-carbaldehyde oxime (OXM) and 5-(thiophen-2-yl)-1H-tetrazole (TET), were synthesized and characterized. Furthermore, their inhibitory property for AA2024-T3 in 1 M HCl solution was investigated via electrochemical and with theoretical study.

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6

Margl, Lilla, Andreas Tei, István Gyurján, and Michael Wink. "GLC and GLC-MS Analysis of Thiophene Derivatives in Plants and in in vitro Cultures of Tagetes patula L. (Asteraceae)." Zeitschrift für Naturforschung C 57, no. 1-2 (2002): 63–71. http://dx.doi.org/10.1515/znc-2002-1-211.

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The occurrence of thiophenic compounds in diverse plant organs and in in vitro root-, callus- and cell suspension cultures of Tagetes patula cv. Carmen was investigated using capillary GLC and GLC-MS. The separation of thiophenes by capillary GLC and the group specific MS fragmentation with the typical sulfur isotope peaks allowed the unequivocal assignment of individual thiophenes in complex mixtures, even when occurring in traces and in the presence of different geometrical isomers. The extracts of Tagetes patula cv. Carmen contained the following 8 thiophene compounds: 5-(3-buten-1-ynyl)-2,

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7

Zhou, Yue, Jie Hao, and Dongbing Zhao. "Divergent synthesis of 3-substituted thieno[3,4-b]thiophene derivatives via hydroxy-based transformations." Materials Chemistry Frontiers 3, no. 7 (2019): 1422–26. http://dx.doi.org/10.1039/c9qm00128j.

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Modular assembly of 3-substituted thieno[3,4-b]thiophenes: we have developed the first Pd-catalytic method to access 3-hydroxythieno[3,4-b]thiophene-2-carboxylate, which can be widely utilized for modular assembly of structurally diverse 3-substituted thieno[3,4-b]thiophene derivatives.

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8

Ibrahim, Sabrin R. M., Abdelsattar M. Omar, Alaa A. Bagalagel, et al. "Thiophenes—Naturally Occurring Plant Metabolites: Biological Activities and In Silico Evaluation of Their Potential as Cathepsin D Inhibitors." Plants 11, no. 4 (2022): 539. http://dx.doi.org/10.3390/plants11040539.

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Naturally, thiophenes represent a small family of natural metabolites featured by one to five thiophene rings. Numerous plant species belonging to the family Asteraceae commonly produce thiophenes. These metabolites possessed remarkable bioactivities, including antimicrobial, antiviral, anti-inflammatory, larvicidal, antioxidant, insecticidal, cytotoxic, and nematicidal properties. The current review provides an update over the past seven years for the reported natural thiophene derivatives, including their sources, biosynthesis, spectral data, and bioactivities since the last review published

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9

Sereda, Grigoriy, Akash Mamon Sarkar, Anwar Hussain, and Nikolai Zefirov. "Solvent-Free and Liquid-Phase Iodination of Thiophene Derivatives with Potassium Dichloroiodate Monohydrate." Synthesis 52, no. 07 (2020): 1140–46. http://dx.doi.org/10.1055/s-0039-1690795.

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Iodination of a series of benzene and thiophene derivatives by potassium dichloroiodate monohydrate was studied with and without a solvent. The liquid substrates tend to be more reactive in water while the solid substrates afford better yields in dichloromethane or under the solvent-free conditions. The 2-substituted thiophenes show good to excellent yields whereas the yield for 3-substituted and 3,4- or 2,4-disubstituted thiophenes and benzene derivatives are significantly lower. The mechanochemical reaction of 5-carbaldehyde-2,2′-bithiophene shows excellent yields, while 2,2′-bithiophene giv

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10

Mahyavanshi, Jyotindra, Snehal Lokhandwala, Jayesh Pandya, and Jigar Patel. "Synthesis, Structural Determination, Docking Study and Bioactivity of Novel Thiophene Derivatives." Asian Journal of Chemistry 36, no. 6 (2024): 1321–26. http://dx.doi.org/10.14233/ajchem.2024.31509.

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The present study reveals 4-methyl-3-(propylamino)thiophene-2-carboxylic acid (Articaine acid) as precursor derivative to synthesize novel thiophene compounds to evaluate their biological activity. The synthesized compounds were subjected to comprehensive characterization techniques including mass spectra, NMR and IR spectroscopy, confirming their structural integrity. Their antimicrobial activity was assessed via minimum inhibitory concentration (MIC) assay against selected bacterial strains. The results emphasize the potential therapeutic applications of these thiophene analogues as efficaci

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11

Li, Yunchuan, Bohuai Xiao, Rongsheng Chen та ін. "Single-molecule conductance investigation of BDT derivatives: an additional pattern found to induce through-space channels beyond π–π stacking". Chemical Communications 55, № 57 (2019): 8325–28. http://dx.doi.org/10.1039/c9cc02998b.

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12

Bolduc, Andréanne, Stéphane Dufresne, Garry S. Hanan, and W. G. Skene. "Synthesis, photophysics, and electrochemistry of thiophene–pyridine and thiophene–pyrimidine dyad comonomers." Canadian Journal of Chemistry 88, no. 3 (2010): 236–46. http://dx.doi.org/10.1139/v09-166.

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A series of new π-conjugated donor (D) and acceptor (A) dyad comonomers were prepared using Suzuki coupling protocols. The D–A comonomers consisting of thiophene/bithiophene as donors and pyridine/pyrimidine as acceptors were prepared to investigate their photophysical and electrochemical properties. The dyads were spectroscopically confirmed to be highly conjugated. This was further supported by the X-ray crystal structure of the bithophene–pyridine dyad that showed all the heterocycles to be coplanar. It was further found that the fluorescence yields (Φfl) of the dyads were highly dependent

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13

Choi, Eunjin, Yuhyeon Jang, Dongil Ho, et al. "Development of Dithieno[3,2-b:2′,3′-d]thiophene (DTT) Derivatives as Solution-Processable Small Molecular Semiconductors for Organic Thin Film Transistors." Coatings 11, no. 10 (2021): 1222. http://dx.doi.org/10.3390/coatings11101222.

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Novel solution-processable dithieno[3,2-d:2′,3′-d]thiophene (DTT) derivatives with alkylated thiophene or alkyl chain substituents, 2,6-bis(5-octylthiophen-2-yl)dithieno[3,2-b:2′,3′-d]thiophene (compound 1), 2,6-bis(5-(2-ethylhexyl)thiophen-2-yl)dithieno[3,2-b:2′,3′-d]thiophene (compound 2), and 2,6-dioctyldithieno[3,2-b:2′,3′-d]thiophene (compound 3), have been synthesized and employed as small molecular organic semiconductors for organic field-effect transistors (OFETs). All compounds exhibited good thermal stability over 290 °C, while different side groups of DTT compounds afforded differen

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14

Hou, Shuai, Hanxiao Tian, Ruiyao Li, et al. "Role of Substitution Patterns in Four Regioisomeric Tetraphenylethylene–Thiophene Derivatives." Molecules 30, no. 14 (2025): 2953. https://doi.org/10.3390/molecules30142953.

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Tetraphenylethylene (TPE)–thiophene compounds are promising candidates for stimuli-responsive luminescent materials, yet systematic investigations into the influence of substitution patterns on their photophysical properties remain limited. Herein, four regioisomeric TPE–thiophene derivatives have been synthesized by systematically varying the number and positions of TPE substituents on the thiophene core. A comprehensive spectroscopic characterization reveals that substitution patterns critically modulate the photoluminescence quantum yields (PLQYs). The ortho-monosubstituted isomer exhibits

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15

Salbeck, Josef, and Erhard Günther. "Elektrochemische und spektroelektrochemische Untersuchungen neuer S-heterochinoider Elektronenakzeptoren, N-Cyanimin-substituierte Thieno[3,2-b]thiophen-2,5-dione / Electrochemical and Spectroelectrochemical Investigations of New S-Heteroquinoid Electron Acceptors, N-Cyanimine Substituted Thieno[3,2-b]thiophene-2,5-diones." Zeitschrift für Naturforschung B 46, no. 3 (1991): 353–60. http://dx.doi.org/10.1515/znb-1991-0315.

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16

Hernández-Téllez, Guadalupe, Sylvain Bernès, Angel Mendoza, et al. "Crystal structures of four chiral imine-substituted thiophene derivatives." Acta Crystallographica Section E Crystallographic Communications 72, no. 3 (2016): 350–54. http://dx.doi.org/10.1107/s2056989016002516.

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A series of thiophenes substituted in positions 2 and 5 by imine groups have been synthesized using a solvent-free approach, and their crystal structures determined. The substituents are chiral groups, and the expected absolute configuration for each molecule was confirmed by refinement of the Flack parameter. The compounds are 2,5-bis[(S)-(+)-(1,2,3,4-tetrahydronaphthalen-1-yl)imino]thiophene, C26H26N2S, (I), 2,5-bis{[(R)-(−)-1-(4-methoxyphenyl)ethyl]iminomethyl}thiophene, C24H26N2O2S, (II), 2,5-bis{[(R)-(−)-1-(4-fluorophenyl)ethyl]iminomethyl}thiophene, C22H20F2N2S, (III), and 2,5-bis{[(S)-(

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17

Sultan Alwan, Ensaf, and Rafat Milad Mohareb. "Synthesis of bioactive heterocyclic compounds using camphor." Bulletin of the Chemical Society of Ethiopia 38, no. 4 (2024): 1069–76. http://dx.doi.org/10.4314/bcse.v38i4.20.

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The aim of the work was to synthesize novel heterocyclic compounds derived from camphor with antibacterial activity. The pyridazine, xanthene, pyranothiazole, pyridinothiazole, thiophene and pyrazole derivatives were produced from 4,11,11-trimethyl-9-phenyl-7-(2-phenylhydrazono)-3,4,5,6,7,9-hexahydro-1H-1,4-methanoxanthen-8(2H)-one (1). Thiophene derivatives 6a,b were produced according to the Gewald’s reaction for thiophene synthesis. On the other hand, pyranothiazol derivatives 8a,b were synthesized by the multicomponent reactions between xanthene derivative 5, benzaldehyde and ethylcyanoace

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18

Lahsasni, Siham, Dunya A. M. Al-Hemyari, Hazem A. Ghabbour, et al. "Synthesis, Characterization, and Antibacterial and Anti-Inflammatory Activities of New Pyrimidine and Thiophene Derivatives." Journal of Chemistry 2018 (August 1, 2018): 1–11. http://dx.doi.org/10.1155/2018/8536063.

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Substituted[4,5]thieno[2,3-d]thiazolo[3,2-a]pyrimidin-5-one (3a–b) and pyrimidin-5(6H)-imine (3c–e) were synthesized via reaction of the starting compounds, ethyl 2-amino-substituted[b]thiophene-3-carboxylate (2a–c) and 2-amino-substituted [b]thiophene-3-carbonitrile (2d–f), respectively, with 2-bromothiazole. Synthesis of (bromo-substituted[b]thiophen-2-yl)alkanamide derivatives (4a–e) and thieno[2,3-d][1,3]oxazin-4-imine derivative (5) was accomplished via reaction of the starting compounds with bromoalkyl chloride through nucleophilic substitution; however, for the synthesis of compound 5,

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19

Damit, E. F., N. Nordin, A. Ariffin, and K. Sulaiman. "Synthesis of Novel Derivatives of Carbazole-Thiophene, Their Electronic Properties, and Computational Studies." Journal of Chemistry 2016 (2016): 1–14. http://dx.doi.org/10.1155/2016/9360230.

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A series of carbazole-thiophene dimers,P1–P9, were synthesized using Suzuki-Miyaura and Ullmann coupling reactions. InP1–P9, carbazole-thiophenes were linked at the N-9 position for different core groups via biphenyl, dimethylbiphenyl, and phenyl. Electronic properties were evaluated by UV-Vis, cyclic voltammogram, and theoretical calculations. Particularly, the effects of conjugation connectivity on photophysical and electrochemical properties, as well as the correlation between carbazole-thiophene and the core, were studied. Carbazole connecting with thiophenes at the 3,6-positions and the p

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20

Demina, Nadezhda S., Nikita A. Kazin, Nikolay A. Rasputin, Roman A. Irgashev, and Gennady L. Rusinov. "Synthesis of aryl-substituted thieno[3,2-b]thiophene derivatives and their use for N,S-heterotetracene construction." Beilstein Journal of Organic Chemistry 15 (November 12, 2019): 2678–83. http://dx.doi.org/10.3762/bjoc.15.261.

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Fiesselmann thiophene synthesis was applied for the convenient construction of thieno[3,2-b]thiophene derivatives. Thus, new 5- or 6-aryl-3-hydroxythieno[3,2-b]thiophene-2-carboxylates were obtained by condensation of 5- or 4-aryl-3-chlorothiophene-2-carboxylates, respectively, with methyl thioglycolate in the presence of potassium tert-butoxide. The saponification of the resulting esters, with decarboxylation of the intermediating acids, gave the corresponding thieno[3,2-b]thiophen-3(2H)-ones. The latter ketones were used to synthesize new N,S-heterotetracenes, namely 9H-thieno[2',3':4,5]thie

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21

Kim, Seongyun, Soomin Ryu, Jihae Ahn, et al. "Solution-Processable Benzo[b]thieno[2,3-d]thiophene Derivatives as Organic Semiconductors for Organic Thin-Film Transistors." Coatings 13, no. 8 (2023): 1417. http://dx.doi.org/10.3390/coatings13081417.

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Two new benzo[b]thieno[2,3-d]thiophene (BTT) derivatives, 2-(benzo[b]thiophen-5-yl)benzo[b]thieno[2,3-d]thiophene (compound 2), and 2-(benzo[b]thieno[2,3-d]thiophene-2yl)dibenzo[b,d]thiophene (compound 3) have been synthesized and utilized as solution-processable small molecular organic semiconductors for organic field-effect transistors (OFETs). The physicochemical characteristics of the recently created substances were analyzed using thermogravimetric analysis (TGA), differential scanning calorimeter (DSC), and UV-vis spectroscopy. Subsequently, the above-mentioned substances were employed a

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22

Geisberger, Thomas, Jessica Sobotta, Wolfgang Eisenreich, and Claudia Huber. "Formation of Thiophene under Simulated Volcanic Hydrothermal Conditions on Earth—Implications for Early Life on Extraterrestrial Planets?" Life 11, no. 2 (2021): 149. http://dx.doi.org/10.3390/life11020149.

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Thiophene was detected on Mars during the Curiosity mission in 2018. The compound was even suggested as a biomarker due to its possible origin from diagenesis or pyrolysis of biological material. In the laboratory, thiophene can be synthesized at 400 °C by reacting acetylene and hydrogen sulfide on alumina. We here show that thiophene and thiophene derivatives are also formed abiotically from acetylene and transition metal sulfides such as NiS, CoS and FeS under simulated volcanic, hydrothermal conditions on Early Earth. Exactly the same conditions were reported earlier to have yielded a pleth

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23

Safonov, A. A. "Study acute toxicity of 4-(R-amino)-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazole-3-thiol in vivo." Farmatsevtychnyi zhurnal, no. 2 (August 14, 2018): 98–101. http://dx.doi.org/10.32352/0367-3057.2.16.06.

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Typically, the system is already known are used as the core for a new substance, which have already proved themselves as potential drugs. So one of these is 1,2,4-triazole ring. The purpose was to study acute toxicity of 4-((R-iden)amino)-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazole-3-thiols and identify possible patterns acute toxicity of the chemical structure of indicators derivatives. In the study of acute contact toxicity was used spreadsheet rapid method for Prozorovsky V. B. Analysis of the results of studies acute toxicity of 1,2,4-triazole derivatives showed that all substanc

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24

Al-Refai, Mahmoud, Basem F. Ali, Ala'a B. Said, Armin Geyer, Michael Marsch, and Klaus Harms. "Synthesis, characterization, crystal structure and supramolecularity of ethyl (E)-2-cyano-3-(3-methylthiophen-2-yl)acrylate and a new polymorph of ethyl (E)-2-cyano-3-(thiophen-2-yl)acrylate." Acta Crystallographica Section E Crystallographic Communications 75, no. 9 (2019): 1357–61. http://dx.doi.org/10.1107/s2056989019011435.

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The synthesis, crystal structure and structural motif of two thiophene-based cyanoacrylate derivatives, namely, ethyl (E)-2-cyano-3-(3-methylthiophen-2-yl)acrylate (1), C11H11NO2S, and ethyl (E)-2-cyano-3-(thiophen-2-yl)acrylate (2), C10H9NO2S, are reported. Derivative 1 crystallized with two independent molecules in the asymmetric unit, and derivative 2 represents a new monoclinic (C2/m) polymorph. The molecular conformations of 1 and the two polymorphs of 2 are very similar, as all non-H atoms are planar except for the methyl of the ethyl groups. The intermolecular interactions and crystal p

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25

Jin, Rongwei, Charles Beromeo Bheeter, and Henri Doucet. "Hindered aryl bromides for regioselective palladium-catalysed direct arylation at less favourable C5-carbon of 3-substituted thiophenes." Beilstein Journal of Organic Chemistry 10 (May 27, 2014): 1239–45. http://dx.doi.org/10.3762/bjoc.10.123.

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The use of the congested aryl bromide 2-bromo-1,3-dichlorobenzene as coupling partner allows to modify the regioselectivity of the arylation of 3-substituted thiophene derivatives in favour of carbon C5. The coupling of this aryl bromide with a variety of 3-substituted thiophenes gave in all cases the desired 5-arylation products in moderate to good yields using only 0.5 mol % of a phosphine-free and air-stable palladium catalyst. Then, from these 5-arylthiophenes, a second palladium-catalysed C–H bond functionalization at C2 of the thiophene ring allows the synthesis of 2,5-diarylthiophenes w

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26

Batista, Rosa M. F., Susana P. G. Costa, Michael Belsley, and M. Manuela M. Raposo. "Synthesis and Characterization of Novel Donor-Acceptor Oligothiophenes as Efficient and Thermally Stable Second-Order Nonlinear Optical Chromophores." Materials Science Forum 636-637 (January 2010): 380–86. http://dx.doi.org/10.4028/www.scientific.net/msf.636-637.380.

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New push-pull thiobarbituric (oligo)thiophene derivatives 1 were synthesized, in good to excellent yields (60-98%), through Knoevenagel condensation of the corresponding formyl-(oligo)thiophenes 2 with 1,3-diethylthiobarbituric acid in dichloromethane, under basic conditions. Evaluation of the thermal and solvatochromic properties of these compounds was carried out and their NLO response was estimated. The values obtained suggest that these (oligo)thiophenes have good potential to be used as novel NLO materials.

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27

Di Maria, Francesca, Mattia Zangoli, and Giovanna Barbarella. "Supramolecular Thiophene-Based Materials: A Few Examples of the Interplay between Synthesis, Optoelectronic Properties and Applications." Organic Materials 03, no. 02 (2021): 321–36. http://dx.doi.org/10.1055/s-0041-1730934.

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Supramolecular nanostructured thiophene based materials with optoelectronic functions are of wide current interest and are playing a crucial role in different fields of nanoscience and nanotechnology. This short review gives a concise report of some particularly interesting examples from our own work concerning thiophene-based supramolecular architectures at multiple length scales, their function and application in devices. We start with some general considerations on the great chemical diversity of thiophene derivatives and their supramolecular architectures. Then we focus on how the supramol

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28

El-Sharkawy, Karam A., Mohammed Al Bratty, Hassan A. Alhazmi, and Asim Najmi. "Design, synthesis, and biological activities of novel thiophene, pyrimidine, pyrazole, pyridine, coumarin and isoxazole: Dydrogesterone derivatives as antitumor agents." Open Chemistry 19, no. 1 (2021): 322–37. http://dx.doi.org/10.1515/chem-2021-0028.

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Abstract On the basis of our consideration to design and to develop antitumor activities of heterocyclic compound derivatives, especially in fused ring system, we refer to the possibility of the heterocyclic extension of one of the most important steroid compounds used as a medicinal drug. The reaction of dydrogesterone with each of the malononitrile or ethylcyanoacetate containing elemental sulfur afforded thiophene derivatives 1a,b. Also, dydrogesterone was reacted with a mixture of ethylcyanoacetate–hydrazine, ethylcyanoacetae–urea, or ethylcyanoacetate–thiourea to produce pyrazole derivati

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29

Hien, Nguyen, and Duong Quoc Hoan. "Synthesis of some mono and dialkynyl derivatives containing thieno[3,2-b]thiophene ring via Sonogashira alkynylation reaction." Tạp chí Khoa học 14, no. 9 (2019): 85. http://dx.doi.org/10.54607/hcmue.js.14.9.2206(2017).

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The Sonogashira cross-coupling reactions were used to synthesize 5 new monoalkynyl derivatives (10a-e) and 2 dialkynyl derivatives (12a-b) containing thieno[3,2-b]thiophene from monoaryl thieno[3,2-b]thiophen in moderate yield. The procedure was optimized and triphenylphosphine (0.2 eq.), palladium diacetate (0.1 eq), copper (I) iodide (0.2 eq.), THF, iPr2NH were found to be the best in these cases. The structures of the (10a-e) and (12a-b) compounds were elucidated by 1H and 13C NMR and mass spectral analysis.

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30

Syed, Afreen* K. Chandra Sekhar. "A Review on Recent Advances of Pharmacological Diversification of Thiophene Derivatives." International Journal of Pharmaceutical Sciences 2, no. 12 (2024): 9–19. https://doi.org/10.5281/zenodo.14253213.

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The heterocyclic compounds have great importance in medicinal chemistry. One of the most important heterocycles in medicinal chemistry are thiophenes possessing wide spectrum of biological properties like anti-cancer, anti-inflammatory, anti-bacterial, anti-fungal, anti-tumor, anti-malarial, anti-microbial, anti-anxiety and many more activities. This skeleton is an important pharmacophore considered as a privileged structure. This review highlights the recent advances in the synthesis of thiophene derivatives with wide variety of pharmacological activities.

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31

Gaber, Hatem M., Mark C. Bagley, Sherif M. Sherif, and Mohsen A. Sayed. "Novel Phenylazo Derivatives of Condensed and Uncondensed Thiophene. Synthesis, Characterization, and Antimicrobial Studies." Zeitschrift für Naturforschung B 66, no. 6 (2011): 585–96. http://dx.doi.org/10.1515/znb-2011-0606.

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In the search for new therapeutic agents against microbial infections, two novel series of monocyclic and tricyclic 5-(phenylazo)thiophene systems were synthesized based on 3-amino-2-thioxopyrimidinone and 2-cyanoacetamidothiophene derivatives 4 and 6. Functionalization of the pyrimidine ring in precursor 4 resulted in the formation of the target tricyclic condensed thiophenes 7, 12, and 13a, b, by the application of a variety of addition, substitution, and condensation reactions. On the other hand, derivatization of the versatile cyanoacetylated compound 6 led to a second series of monocyclic

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Irgashev, Roman A., and Nikita A. Kazin. "Synthesis of Thieno[3,2-b]thiophenes from 2,5-Dicarbonyl 3-Nitrothiophenes via Nucleophilic Aromatic Substitution of the Nitro Group with Thiolates." Organics 5, no. 4 (2024): 507–19. http://dx.doi.org/10.3390/org5040027.

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In this study, we developed an efficient strategy for constructing thieno[3,2-b]thiophene molecules from 3-nitrothiophenes, containing carbonyl fragments at the C-2 and C-5 atoms, by nucleophilic aromatic substitution of the nitro group in these substrates. It was shown that the reaction of 3-nitrothiophene-2,5-dicarboxylates with thiophenols, thioglycolates and 2-mercaptoacetone in the presence of K2CO3 proceeds rapidly via nucleophilic displacement of the nitro group with the formation of 3-sulfenylthiophene-2,5-dicarboxylates. Further treatment of the resulting thiophene-2,5-dicarboxylates,

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Rajni Swamy, V., P. Gunasekaran, R. V. Krishnakumar, N. Srinivasan, and P. Müller. "Crystal structure of [4-(2-methoxyphenyl)-3-methyl-1-phenyl-6-trifluoromethyl-1H-pyrazolo[3,4-b]pyridin-5-yl](thiophen-2-yl)methanone." Acta Crystallographica Section E Structure Reports Online 70, no. 9 (2014): o974—o975. http://dx.doi.org/10.1107/s1600536814017437.

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The title compound, C26H18F3N3O2S, a 2-methoxy-substituted derivative, is closely related to its 4-methyl- and 4-chloro-substituted analogues and yet displays no structural relationships with them. The thiophene ring is disorder free and the –CF3group exhibits disorder, respectively, in contrast and similar to that observed in the 4-methyl- and 4-chloro-substituted derivatives. The torsion angle which defines the twist of the thiophene ring is −69.6 (2)° (gauche) in the title compound, whereas it is anticlinal in the 4-methyl- and 4-chloro-substituted derivatives, with respective values of 99.

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Tivari, Sunil, Siddhant V. Kokate, Uttam B. Shelar, and Yashwantsinh Jadeja. "THE DESIGN, SYNTHESIS AND BIOLOGICAL EVALUATION OF THE PEPTIDE DERIVATIVES CONTAINING GUANIDINE MOIETY WITH 5-CHLORO-THIOPHENE-2-CARBOXYLIC ACID CONJUGATES." RASAYAN Journal of Chemistry 15, no. 02 (2022): 875–84. http://dx.doi.org/10.31788/rjc.2022.1526907.

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A new series of dipeptide derivatives with 5-chloro-thiophene-2-carboxylic acid conjugates have been designed and synthesized using solid-phase peptide synthesis. The synthesized dipeptide derivatives were characterized by using spectroscopic tools, like 1H and 13C NMR, IR, and mass and elemental analysis. Additionally, the obtained target dipeptide derivatives were evaluated for in vitro antimicrobial activity. The antibacterial activity of the target compounds was evaluated against four bacteria (two Gram-positive; Streptococcus pyogenes and Staphylococcus aureus, two Gram-negative; Escheric

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35

Ryu, Seunghyup, Chaeyoung Yun, Soomin Ryu, Jihae Ahn, Choongik Kim, and Sungyong Seo. "Characterization of [1]Benzothieno[3,2-b]benzothiophene (BTBT) Derivatives with End-Capping Groups as Solution-Processable Organic Semiconductors for Organic Field-Effect Transistors." Coatings 13, no. 1 (2023): 181. http://dx.doi.org/10.3390/coatings13010181.

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Solution-processable [1]benzothieno[3,2-b]benzothiophene (BTBT) derivatives with various end-capping groups, 2-(phenylethynyl)benzo[b]benzo[4,5]thieno[2,3-d]thiophene (Compound 1), 2-octyl-7-(5-(phenylethynyl)thiophen-2-yl)benzo[b]benzo[4,5]thieno[2,3-d]thiophene (Compound 2), and triisopropyl((5-(7-octylbenzo[b]benzo[4,5]thieno[2,3-d]thiophen-2-yl)thiophen-2-yl)ethynyl)silane (Compound 3), have been synthesized and characterized as active layers for organic field-effect transistors (OFETs). Thermal, optical, and electrochemical properties of the newly synthesized compounds were characterized

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Miao, Kai, Mao Liang, Zhihui Wang, Chunyao Zhang, Zhe Sun, and Song Xue. "Organic sensitizers featuring thiophene derivative based donors with improved stability and photovoltaic performance." Physical Chemistry Chemical Physics 19, no. 3 (2017): 1927–36. http://dx.doi.org/10.1039/c6cp07335b.

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Thiophene derivatives, including thieno[3,2-b][1]benzothiophene (TBT), benzo[b]thiophene (BT), 2-phenylthieno[3,2-b]thiophene (PTT) and 2-phenylthiophene (PT), have been introduced as donor for construction triarylamine organic dyes.

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Kharizomenova, I. A., A. N. Grinev, N. V. Kaplina, et al. "Functional derivatives of thiophene." Pharmaceutical Chemistry Journal 19, no. 9 (1985): 621–22. http://dx.doi.org/10.1007/bf00766844.

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Mishra, Raghav, Nitin Kumar, Isha Mishra, and Neetu Sachan. "A Review on Anticancer Activities of Thiophene and Its Analogs." Mini-Reviews in Medicinal Chemistry 20, no. 19 (2020): 1944–65. http://dx.doi.org/10.2174/1389557520666200715104555.

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Cancer is the world's second-largest cause of mortality and one of the biggest global health concerns. The prevalence and mortality rates of cancer remain high despite significant progress in cancer therapy. The search for more effective, as well as less toxic treatment methods for cancer, is at the focus of current studies. Thiophene and its derivatives have surged as an influential scaffold, which, because of their appreciable diversity in biological activities, has drawn the concerned interest of the researchers in the field of medicinal chemistry. By the affluent introduction of its deriva

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Mohareb, Rafat M., Amira E. M. Abdallah, and Ebtsam A. Ahmed. "Synthesis and cytotoxicity evaluation of thiazole derivatives obtained from 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene- 3-carbonitrile." Acta Pharmaceutica 67, no. 4 (2017): 495–510. http://dx.doi.org/10.1515/acph-2017-0040.

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Abstract Reactivity of 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3- carbonitrile towards thioglycolic acid resulted in thiazole derivative 1. The latter reacted with different chemical reagents to give thiazole, pyrano[2,3-d]thiazole and thiazolo[ 4,5-d]thiazole derivatives. Cytotoxicity effects of the newly synthesized products against six cancer cell lines, namely, human gastric cancer (NUGC), human colon cancer (DLD- 1), human liver cancer (HA22T and HEPG-2), human breast cancer (MCF) and nasopharyngeal carcinoma (HONE-1) as well as against a normal fibroblast cell (WI-38) were evaluated.

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Li, Yibiao, Liang Cheng, Xiaohang Liu, Bin Li, and Ning Sun. "Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes." Beilstein Journal of Organic Chemistry 10 (December 4, 2014): 2886–91. http://dx.doi.org/10.3762/bjoc.10.305.

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An efficient copper-promoted hydration reaction and its application in the synthesis of benzo[b]furan and benzo[b]thiophene derivatives is presented starting from readily available 2-fluorophenylacetylene derivatives. The key annulation step involves the hydration of the C–F bond of 2-fluorophenylacetylene derivatives followed by an intramolecular annulation to afford benzo[b]furan and benzo[b]thiophene derivatives. Moreover, structurally important 2,2'-bisbenzofuran scaffolds are provided in good yields.

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Siutkina, Alena I., Ramiz R. Makhmudov, and Daria A. Shipilovskikh. "Synthesis and analgesic activity evaluation of derivatives of 2-[(1,4-dioxo-1-amino-4-arylbutyl-2-en-2-yl)amino]-4,5,6,7-tetrahydrobenzo[<i>b</i>]thiophene-3-carboxylic acid." Chimica Techno Acta 8, no. 4 (2021): 20218404. http://dx.doi.org/10.15826/chimtech.2021.8.4.04.

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The synthesis of new derivatives of 2-[(1,4-dioxo-1-amino-4-arylbutyl-2-en-2-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid is described. Starting 2-{[5-aryl-2-oxofuran-3(2H)-ylidene]amino}thiophene-3-carboxylic acids were obtained by intramolecular cyclisation of substituted 4-aryl-4-oxo-2-thienylaminobut-2-enoic acids in acetic anhydride. New derivatives of 2-[(1,4-dioxo-1-amino-4-arylbutyl-2-en-2-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acids were obtained via decyclization reaction of 2-{[5-aryl-2-oxofuran-3(2H)-ylidene]amino}thiophene-3-carboxylic acids.

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Souza, Beatriz, Tiago De Oliveira, Thiago Aquino, et al. "Preliminary antifungal and cytotoxic evaluation of synthetic cycloalkyl[b]thiophene derivatives with PLS-DA analysis." Acta Pharmaceutica 62, no. 2 (2012): 221–36. http://dx.doi.org/10.2478/v10007-012-0017-y.

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Preliminary antifungal and cytotoxic evaluation of synthetic cycloalkyl[b]thiophene derivatives with PLS-DA analysis A series of 2-[(arylidene)amino]-cycloalkyl[b]thiophene-3-carbonitriles (2a-x) was synthesized by incorporation of substituted aromatic aldehydes in Gewald adducts (1a-c). The title compounds were screened for their antifungal activity against Candida krusei and Criptococcus neoformans and for their antiproliferative activity against a panel of 3 human cancer cell lines (HT29, NCI H-292 and HEP). For antiproliferative activity, the partial least squares (PLS) methodology was app

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43

Wang, Qing Xiu, Li Jie Duan, Bo Yang Qu, Juan Wang, and Fu De Liu. "Synthesis and Optical/Electrochemical Properties of Conjugated Polymers with Diphenyl and Thiophene in Main Chain." Advanced Materials Research 1035 (October 2014): 497–501. http://dx.doi.org/10.4028/www.scientific.net/amr.1035.497.

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Two thiophene derivatives 4,4'-di (thiophen-2-yl) biphenyl and 4,4'-di (thiophen-2-yl) -2-nitrobiphenyl ,which were used as monomers for preparing poly (4,4'-di (thiophen-2-yl) biphenyl) (DPBT) and poly (4,4'-di (thiophen-2-yl)-2-nitrobiphenyl) (DPNT) by ferric chloride oxidation polymerization, were synthesized via Suzuki reaction with 4,4'-dibromobiphenyl as the raw material. UV-vis absorption spectra, fluorescence spectra, photoluminescence spectra and electrochemical properties of the polymers were recorded and used for calculating the band-gap (Eg), HOMO orbital energy (EHOMO) and LUMO or

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44

El-Metwally, Souad A., Ali K. Khalil, Abeer M. El-Naggar, and Wael M. El-Sayed. "Novel Tetrahydrobenzo [b] Thiophene Compounds Exhibit Anticancer Activity through Enhancing Apoptosis and Inhibiting Tyrosine Kinase." Anti-Cancer Agents in Medicinal Chemistry 18, no. 12 (2019): 1761–69. http://dx.doi.org/10.2174/1871520618666180813120558.

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Background: Developing new chemotherapeutic agents with molecular targets, larger margin of safety against normal cells and low cost is the target many scientists try to achieve. Objective: The present study was undertaken to investigate the anticancer activity of a novel series of thiophene compounds and the molecular mechanisms associated. Method: A series of novel heterocyclic compounds including pyrimidine derivatives (2, 3, 4, 5 8, 11, 12, 13, 14, and 15), thiophene derivatives (6, 7, and 10) and oxoisothiazolidine derivative (9) was synthesized from 4,5,6,7- tetrahydrobenzo[b] thiophene

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Abdo, Nadia Y. Megally, Rafat M. Mohareb, and Waleed N. Al-darkazali. "Heterocyclization of 2-Arylidenecyclohexan-1,3-dione: Synthesis of Thiophene, Thiazole, and Isoxazole Derivatives with Potential Antitumor Activities." Anti-Cancer Agents in Medicinal Chemistry 20, no. 3 (2020): 335–45. http://dx.doi.org/10.2174/1871520619666190730103425.

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Background: Thiophene, thiazole, and isoxazole derivatives are present in a wide range of natural and synthetic compounds with heterogeneous pharmacological activity. Due to their structural diversity, they are some of the most versatile classes of compounds for anticancer drug design and discovery. Objective: Thiophene, thiazole, and isoxazole derivatives were herein designed with a dual purpose: as antiproliferative agents and kinase inhibitors. Methods: The test compounds were synthesized in moderate to high yields through a simple methodology. Tetrahydrobenzo[b]thiophen-5-one derivatives 5

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Endo, T., M. Rikukawa, and K. Sanui. "Regiocontrolled synthesis of poly(thiophene) derivatives: EL devices utilizing chiral poly(thiophene) derivatives." Synthetic Metals 119, no. 1-3 (2001): 191–92. http://dx.doi.org/10.1016/s0379-6779(00)00687-1.

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Masih, Prerna J., Tanay Kesharwani, Elivet Rodriguez, et al. "Synthesis and Evaluation of 3-Halobenzo[b]thiophenes as Potential Antibacterial and Antifungal Agents." Pharmaceuticals 15, no. 1 (2021): 39. http://dx.doi.org/10.3390/ph15010039.

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The global health concern of antimicrobial resistance has harnessed research interest to find new classes of antibiotics to combat disease-causing pathogens. In our studies, 3-halobenzo[b]thiophene derivatives were synthesized and tested for their antimicrobial activities using the broth microdilution susceptibility method. The 3-halo substituted benzo[b]thiophenes were synthesized starting from 2-alkynyl thioanisoles using a convenient electrophilic cyclization methodology that utilizes sodium halides as the source of electrophilic halogens when reacted along with copper(II) sulfate. This env

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48

Shashidhara GS, Sahana KP, Shazia, Tejaswini, and Madavi Sunitha. "Synthesis, Characterization of thiophene derivatives and its biological applications." World Journal of Advanced Research and Reviews 26, no. 3 (2025): 687–701. https://doi.org/10.30574/wjarr.2025.26.3.2227.

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In this research work, titled “Synthesis, Characterization of thiophene derivatives and its biological activity” is related to studies towards the synthesis of Sulphur containing ligands that is thiophene derivatives. The newly synthesized compounds are characterized by FT-IR, 13C-NMR,1H NMR techniques. And all the compounds were tested for antibacterial activity. The complexes showed low antibacterial activity.

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49

Uozumi, Yasuhiro, Anggi Eka Purta, Shun Ichii, and Aya Tazawa. "C−H Arylation of Thiophenes with Aryl Bromides by a Parts-per-Million Loading of a Palladium NNC-Pincer Complex." Synlett 31, no. 16 (2020): 1634–38. http://dx.doi.org/10.1055/s-0040-1707213.

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A palladium NNC-pincer complex efficiently catalyzed the direct arylation of thiophene derivatives with extremely low palladium loadings of the order of parts per million. Thus, the reaction of various thiophenes with aryl bromides in the presence of 25–100 mol ppm of chlorido[(2-phenyl-κ-C 2)-9-phenyl-1,10-phenanthroline-κ2-N,N′]palladium(II) NNC-pincer complex, K2CO3, and pivalic acid in N,N-dimethylacetamide afforded the corresponding 2- or 5-arylated thiophenes in good to excellent yields. A combination of the present C–H arylation and Hiyama coupling with the same NNC-pincer complex prov

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Lahiri, Sikha, and P. K. Sen. "ChemInform Abstract: Cyclohepta[b]thiophene Derivatives. Part 4. Dehydrogenation of Cyclohepta[b]thiophene and Cyclohepta[c]thiophene Derivatives." ChemInform 31, no. 19 (2010): no. http://dx.doi.org/10.1002/chin.200019053.

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