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Journal articles on the topic 'Bis(2'-thienyl)pyrazine derivatives'

Author: Grafiati

Published: 4 June 2021

Last updated: 10 February 2022

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1

Keshtov, M. L., V. S. Kochurov, Ganesh Datt Sharma, and A. R. Khokhlov. "Synthesis of new conjugated copolymers containing 4,8-bis(dodecyloxy)benzo[1,2-b:4,5-b′]dithiophene/5,7-bis(3,4-diethylthien-2-yl)-2,3-diphenylthieno[3,4-b]pyrazine and 4,8-bis(dodecyloxy)benzo[1,2-b:4,5-b′]dithiophene/4,6-di(3,4-diethylthien-2-yl)-thieno[3,4-c][1,2,5]thiadiazole derivatives for photovoltaic applications." Polymer Science Series B 55, no. 5-6 (May 2013): 373–81. http://dx.doi.org/10.1134/s1560090413060067.

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2

Mørkved, Eva H., Nils K. Afseth, and Helge Kjøsen. "Zn(quinoline)2Cl2: an efficient reagent for synthesis of zinc azaphthalocyanines with thiomorpholine- or pyrazole substituents." Journal of Porphyrins and Phthalocyanines 10, no. 11 (November 2006): 1301–8. http://dx.doi.org/10.1142/s1088424606000673.

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The Zn ( quinoline )2 Cl 2 complex is found to be a convenient reagent for the direct synthesis of amino-substituted, zinc azaphthalocyanines. Octa(4-thiomorpholinyl)- and octa(1-pyrazolyl)- substituted zinc azaphthalocyanines were synthesized from pyrazines, 5,6-bis(4-thiomorpholinyl)pyrazine-2,3-dicarbonitrile and 5,6-bis(1-pyrazolyl)pyrazine-2,3-dicarbonitrile, respectively and dry Zn ( quinoline )2 Cl 2. Two zinc azaphthalocyanines, both mixtures of four constitutional isomers, were synthesized by the same method, from 6-(2-thienyl)-5-(4-thiomorpholinyl)pyrazine-2,3-dicarbonitrile and from 6-(2-thienyl)-5-(1-pyrazolyl)pyrazine-2,3-dicarbonitrile respectively. The octa(4-thiomorpholinyl)- and octa(1-pyrazolyl)-substituted zinc azaphthalocyanines and the zinc azaphthalocyanines with mixed substituents were characterized by elemental analyses, TOF-SIMS, 1 H and 13 C NMR, and UV-vis spectroscopic methods. Q-bands for octa(4-thiomorpholinyl)- and octa(1-pyrazolyl)-substituted zinc azaphthalocyanines and the zinc azaphthalocyanines with mixed substituents are found at respectively 655 and 670 nm (ɛ: 100 000-180 000 M-1.cm-1).

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3

Popek, Rafal, and Guy Crundwell. "Crystal structures of 2,3-bis(thiophen-2-yl)pyrido[2,3-b]pyrazine and 7-bromo-2,3-bis(thiophen-2-yl)pyrido[2,3-b]pyrazine." Acta Crystallographica Section E Crystallographic Communications 75, no. 1 (January 1, 2019): 89–93. http://dx.doi.org/10.1107/s2056989018016882.

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The crystal structures of 2,3-bis(thiophen-2-yl)pyrido[2,3-b]pyrazine, C15H9N3S2 (1), and 7-bromo-2,3-bis(thiophen-2-yl)pyrido[2,3-b]pyrazine, C15H8BrN3S2 (2), are discussed. Both molecules crystallize in space group P21/c. In 1, the thienyl rings are inclined to the mean plane of the pyridopyrazine moiety by 6.16 (7) and 86.66 (8)°, where as in 2 the corresponding dihedral angles are 33.29 (11) and 19.84 (9)°. The pyridopyrazine moiety is relatively planar in 1 with the two rings being inclined to each other by 1.33 (7)°. In 2, however, the pyridopyrazine moiety is buckled with the corresponding dihedral angle being larger at 8.78 (10)°. In the crystal of 1, the packing creates intersecting bilayers; the layering results from the pyridopyrazine moieties being engaged in offset π-stacking, where the interplanar distance is 3.431 (9) Å with an offset 1.14 Å. In the crystal of 2, the molecules pack head-to-head and are linked by a series of C—H...Br and C—H...N intermolecular interactions, forming layers parallel to the ab plane.

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4

Jurášek, Adolf, Vladimír Žvak, Jaroslav Kováč, Oľga Rajniaková, and Jarmila Štetinová. "Synthesis and reactions of β-substituted derivatives of furan." Collection of Czechoslovak Chemical Communications 50, no. 9 (1985): 2077–83. http://dx.doi.org/10.1135/cccc19852077.

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The 1,4-cycloaddition reaction of 4-phenyl-1,3-oxazole to 2-propinyl benzoate and dimethyl butinedioate afforded the respective 3-furylmethyl benzoate (I) and 3,4-bis(methoxycarbonyl)furan (II). These compounds served for the synthesis of 3-chloromethylfuran and 3,4-bis(chloromethyl)furan, which afforded via Wittig reaction 3-(β-arylvinyl)furans III (aryl = 5-nitro-2-furyl (IIIa), 5-nitro-2-thienyl (IIIb), 1-methyl-4-nitro-2-pyrrolyl (IIIc), and 4-nitrophenyl (IIIe)) and 3,4-bis(β-arylvinyl)furans IV (aryl = 5-nitrofuryl (IVa), 5-nitro-2-thienyl (IVc), and 4-nitrophenyl (IVd)). According to spectral evidence (1H NMR, IR, UV spectra), compound IIIa and IIIb originated as E isomers, whilst the remaining products are a mixture of E and Z isomers; some couples were succeded to separate.

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5

Pu, Shouzhi, Shengsheng Zhu, Yi Rao, Gang Liu, and Huizhen Wei. "Photochromism of 1,2-bis(2-n-alkyl-5-formyl-3-thienyl)perfluorocyclopentene derivatives." Journal of Molecular Structure 921, no. 1-3 (March 2009): 89–100. http://dx.doi.org/10.1016/j.molstruc.2008.12.039.

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6

Galindo, Miguel A., Jennifer Hannant, Ross W. Harrington, William Clegg, Benjamin R. Horrocks, Andrew R. Pike, and Andrew Houlton. "Pyrrolyl-, 2-(2-thienyl)pyrrolyl- and 2,5-bis(2-thienyl)pyrrolyl-nucleosides: synthesis, molecular and electronic structure, and redox behaviour of C5-thymidine derivatives." Organic & Biomolecular Chemistry 9, no. 5 (2011): 1555. http://dx.doi.org/10.1039/c0ob00466a.

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7

Kitamura, Chitoshi, Shoji Tanaka, and Yoshiro Yamashita. "Synthesis of new narrow bandgap polymers based on 5,7-di(2-thienyl)thieno[3,4-b]pyrazine and its derivatives." Journal of the Chemical Society, Chemical Communications, no. 13 (1994): 1585. http://dx.doi.org/10.1039/c39940001585.

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8

Tatsumi, Yuto, Jun-ichiro Kitai, Waka Uchida, Koji Ogata, Shinichiro Nakamura, and Kingo Uchida. "Photochromism of 1,2-Bis(2-thienyl)perfluorocyclopentene Derivatives: Substituent Effect on the Reactive Carbon Atoms." Journal of Physical Chemistry A 116, no. 45 (November 2012): 10973–79. http://dx.doi.org/10.1021/jp3092978.

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9

Toyota, Kozo, Hiroshi Katsuta, Takeaki Iwamoto, and Noboru Morita. "Preparation of 1,4-bis(2-ethynyl-3-thienyl) benzene derivatives linked by oligo(ethyleneglycol) chain." Heteroatom Chemistry 22, no. 3-4 (2011): 531–37. http://dx.doi.org/10.1002/hc.20718.

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10

Toyota, Kozo, Hiroshi Katsuta, Takeaki Iwamoto, and Noboru Morita. "Preparation of 1,4-bis(2-ethynyl-3-thienyl)benzene derivatives linked by oligo(ethyleneglycol) Chain." Heteroatom Chemistry 23, no. 1 (2012): 122. http://dx.doi.org/10.1002/hc.20757.

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11

Yang, Jongtae, M. V. Lakshmikantham, Michael P. Cava, Dominique Lorcy, and Joelle Rault Bethelot. "Synthesis and Characterization of 5,10-Bis(2-thienyl)indeno[2,1-a]indene Derivatives: The First Examples of Conducting Polymers Containing a Rigid Bis(thienyl)butadiene Core." Journal of Organic Chemistry 65, no. 20 (October 2000): 6739–42. http://dx.doi.org/10.1021/jo991140y.

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12

Blockhuys, F., R. Hoefnagels, C. Peten, C. Van Alsenoy, and H. J. Geise. "Cis / trans -isomerizations in 1,2-bis(2-thienyl)ethene derivatives: a joint experimental and computational approach." Journal of Molecular Structure 485-486 (August 1999): 87–96. http://dx.doi.org/10.1016/s0022-2860(99)00180-5.

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13

Dagley, IJ, and JL Flippenanderson. "Synthesis of Cyclic Nitramines From Products of the Cyclocondensation Reaction of Guanidine With 2,3,5,6-Tetrahydroxypiperazine-1,4-dicarbaldehyde." Australian Journal of Chemistry 47, no. 11 (1994): 2033. http://dx.doi.org/10.1071/ch9942033.

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The reaction of 2,3,5,6-tetrahydroxypiperazine-1,4-dicarbaldehyde (1) with guanidine hydrochloride in hydrochloric acid can be controlled to give 2,6-diiminododecahydrodiimidazo[4,5-b:4′,5′-e] pyrazine (2a) or the cis isomer of 4,5-diamino-2-iminoimidazolidine (4). Compound (4) reacts with formaldehyde, or formic acid followed by reduction, to give 2-iminooctahydroimidazo[4,5-d] imidazole (7). Treatment of (2a) or (7) with nitric acid gives dinitro derivatives that were isolated as nitric acid salts of the cyclic guanidines. Reaction of the dinitro derivatives with nitric acid/acetic anhydride in the presence of chloride ion gives 4,8-dinitro-2,6-bis( nitroimino ) dodecahydrodiimidazo -[4,5-b:4′,5′-e] pyrazine (3a) and 1,3-dinitro-5-( nitroimino ) octahydroimidazo [4,5-d] imidazole (9). The reaction of (7) with nitric acid/ trifluoroacetic anhydride was controlled to give either the tetranitro or a dinitro bis ( trifluoroacetyl ) derivative of the corresponding bicyclic urea.

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14

Jiang, Liang, Hu Gao, Lizhi Gai, and Zhen Shen. "J-Aggregation induced emission enhancement of a thienyl substituted bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine (BOPHY) dye." New Journal of Chemistry 42, no. 10 (2018): 8271–75. http://dx.doi.org/10.1039/c8nj00031j.

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15

Yang, Jongtae, M. V. Lakshmikantham, Michael P. Cava, Dominique Lorcy, and Joelle Rault Bethelot. "ChemInform Abstract: Synthesis and Characterization of 5,10-Bis(2-thienyl)indeno[2,1-a]indene Derivatives: The First Examples of Conducting Polymers Containing a Rigid Bis(thienyl)butadiene Core." ChemInform 32, no. 5 (January 30, 2001): no. http://dx.doi.org/10.1002/chin.200105095.

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16

Prousek, Josef, and Viktor Hayden. "Preparation and electron transfer-induced cis-trans isomerization reactions of 1-(5-nitro-2-furyl)-, 1-(5-nitro-2-thienyl)-, and 1-(4-nitrophenyl)-2-R ethylenes." Collection of Czechoslovak Chemical Communications 54, no. 6 (1989): 1675–82. http://dx.doi.org/10.1135/cccc19891675.

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Mixtures of E- and Z-isomers of 1,2-bis(5-nitro-2-furyl)ethylene (I), 1-(5-nitro-2-furyl)-2-(4-nitrophenyl)ethylene (II), 1,2-bis(4-nitrophenyl)ethylene (III), 1-(5-methoxycarbonyl-2-furyl)-2-(4-nitrophenyl)ethylene (IV), 1-(5-methoxycarbonyl-2-furyl)-2-(5-nitro-2-furyl)ethylene (V) and 1-(5-methoxycarbonyl-2-furyl)-2-(5-nitro-2-thienyl)ethylene (VI) were prepared by the Wittig reaction. These derivatives were isomerized by electron transfer-induced reactions via the radical anion in the CT-complex using aniline as electron donor at 25 °C in the light or at 80 °C in the dark. The starting as well as the final E:Z ratio was determined by 1H NMR spectroscopy. In all cases only the cis → trans isomerization was observed.

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17

Brown, Darren, Seema Muranjan, and Randolph P. Thummel. "The Preparation and Study of Bis(2-quinolyl) and Bis(2-[1,8]naphthyridyl) Derivatives of Pyrimidine and Pyrazine as Bridging Ligands for RuII." European Journal of Inorganic Chemistry 2003, no. 19 (October 2003): 3547–53. http://dx.doi.org/10.1002/ejic.200300185.

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18

Amr, Abdel-Galil E. "Synthesis of Some New Linear and Chiral Macrocyclic Pyridine Carbazides as Analgesic and Anticonvulsant Agents." Zeitschrift für Naturforschung B 60, no. 9 (September 1, 2005): 990–98. http://dx.doi.org/10.1515/znb-2005-0914.

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A series of 2,6-disubstituted pyridine derivatives were prepared from 2,6-diacetylpyridine or 2,6- dicarbonyl pyridine dichloride as starting materials. Reaction of 2,6-diacetylpyridine 1 with hydroxylamine hydrochloride or different aromatic aldehydes afforded the corresponding 2,6-diacetylpyridine dioxime and 2,6-bis-[β -(2-thienyl)acryloyl]pyridine derivatives 2 and 3, respectively. Additionally, N2,N2‘-(pyridine-2,6-dicarbonyl)-L-amino acid hydrazides 5 were prepared starting from 2,6- dicarbonyl pyridine dichloride via the corresponding esters 4. Compound 3 was reacted with hydroxylamine hydrochloride to afford the 2,6-bis-[β -(2-thienyl)acryloyl-oxime]-pyridine derivative 6. Treatment of compounds 2 or 6 with phenyl isocyanate or phenyl isothiocyanate in refluxing dioxane gave the corresponding semicarbazide or thiosemicarbazide derivatives 7 and 8, respectively. Their treatment with toluene-3,5-diisocyanate afforded the macrocyclic semicarbzides 9 and 10, respectively. The chiral thiosemicarbazides 11a,b were however, prepared by treating compounds 5a,b with phenyl isothiocyanate followed by cyclization with sodium hydroxide (2N) yielding the triazoles 12a,b. Finally, the hydrazides 5a,b were treated with toluene-3,5-diisocyanate to afford the chiral macrocyclic tetrapeptide semicarbazides 13a,b in reasonable yields, while the expected cyclic dipeptide 14 was not formed. The structure assignments of the new compounds were based on chemical and spectroscopic evidence. The pharmacological screening showed that many of these compounds have good analgesic and anticonvulsant activities comparable to Voltarine® and Carbamazapine® used as reference drugs.

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19

Toyota, Kozo, Yasutomo Tsuji, and Noboru Morita. "Chemistry of bis(2-ethynyl-3-thienyl)arene and related systems. Part 6: preparation of 1,4-bis(2-ethynyl-3-thienyl)benzene derivatives containing fluorine atoms at the 2,3- or 2,5-positions of the benzene ring." Journal of Sulfur Chemistry 30, no. 3-4 (June 29, 2009): 351–59. http://dx.doi.org/10.1080/17415990902913370.

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20

Laduree, Daniel, Jean Charles Lancelot, Max Robba, E. Chenu, and G. Mathe. "Synthesis and evaluation of antileukemic activity of 5-thienyl- or 5-(2-furyl)-2,3-dihydro-6,7-bis(hydroxymethyl)-1H-pyrrolizine bis(alkylcarbamates) and derivatives." Journal of Medicinal Chemistry 32, no. 2 (February 1989): 456–61. http://dx.doi.org/10.1021/jm00122a028.

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21

Outurquin, Francis, and Claude Paulmier. "Acid catalyzed α-alkylation of β-Aminothiophenes using aldehydes and selenophenol synthesis of bis(3-amino-2-thienyl)methane derivatives." Tetrahedron Letters 34, no. 36 (September 1993): 5715–18. http://dx.doi.org/10.1016/s0040-4039(00)73841-x.

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22

Pastor, Joaquín, Sonsoles Rodríguez-Arístegui, Ana Isabel Hernández, Carmen Varela, Antonio Salgado, and Sonia Martínez. "New use of bis(benzotriazolyl)-1,2-(dialkylamino)ethanes for the synthesis of 2-H-3-dialkylamino imidazo[1,2-a]pyrazine derivatives." Tetrahedron Letters 53, no. 9 (February 2012): 1082–84. http://dx.doi.org/10.1016/j.tetlet.2011.12.077.

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23

Gutiérrez, Angel, M. Felisa Perpiñán, Ana E. Sánchez, M. Carmen Torralba, M. Rosario Torres, and M. Pilar Pardo. "Influence of the counter anion and solvent in the structure of copper derivatives with the 2,3-bis(2-pyridyl)pyrazine ligand." Inorganica Chimica Acta 363, no. 11 (August 2010): 2443–51. http://dx.doi.org/10.1016/j.ica.2010.03.080.

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24

Semire, Banjo, and Olusegun Ayobami Odunola. "Density Functional Theory (DFT) Study on α,α-Bis(2-benzothiophen-1-yl)-4H-cyclopenta[2,1-b,3;4-b′]dithiophene Derivatives for Optoelectronic Devices." Journal of Pure and Applied Chemistry Research 8, no. 2 (August 1, 2019): 126–39. http://dx.doi.org/10.21776/ub.jpacr.2019.008.02.438.

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Bis(2-benzothiophen-1-yl)-4H-cyclopenta[2,1-b,3;4-b′]dithiophene derivatives comprised of three series; bis(2-thienyl)-4H-cyclopenta[2,1-b,3;4-b]dithiopene (BTDT), diphenyl4Hcyclopenta[2,1-b,3;4-b]dithiophene (DPDT) and bis(2-benzothiophen-1-yl)-4Hcyclopenta[2,1-b,3;4-b]dithiophene (BBDT) have been studied using Density Functional Theory (B3LYP/6-31G**). In each series, molecules with C=S bridge exhibited the lowest band gap; for instance in BBDT series, the energy band gap could be arranged as 2.29, 2.23 and 1.66 eV for CH2, C=O and C=S bridge respectively. The low band gaps calculated for BBDT-C=S (1.66 eV) and BTDT-C=S (1.82 eV) could facilitate photo-excited electron transfer as one the criteria for a molecule to be used in photovoltaic devices. Also, the results showed that longest UV-vis absorption wavelength was observed for molecules with C=S bridge, i.e. 1013.66, 874.75 and 1097.66 nm for BTDT, DPDT and BBDT respectively. The polarizability (α0) valves calculated for the molecules follow as -CH2 < C=O < C=S bridge in each series, indicating that the higher the polarizability (α0) valve the longer the λmax nm and the lower the energy band gap. The magnitude of the molecular hyperpolarizability β0 showed that molecular structures with -C=O bridge could be best NLO material in each series.

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25

OUTURQUIN, F., and C. PAULMIER. "ChemInform Abstract: Acid-Catalyzed α-Alkylation of β-Aminothiophenes Using Aldehydes and Selenophenol. Synthesis of Bis(3-amino-2-thienyl)methane Derivatives." ChemInform 24, no. 48 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199348145.

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26

Zhuang, Xiao Xiao, Xiao Long Lei, and Xiao Xia Sun. "The Synthesis of Novel Oligomer 4,8-Di(4-hexyl-2-thienyl)-2λ⁴δ²-Benzo[1,2-c;4,5-c’]bis[1,2,5]-Thiadiazole." Advanced Materials Research 602-604 (December 2012): 696–99. http://dx.doi.org/10.4028/www.scientific.net/amr.602-604.696.

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Heterocyclic oligomer based on BBT bearing solubilizing side chains have been synthesized in high yields over six steps from readily available starting materials. This approach offers a much milder, shorter, and more efficient route to BBT derivatives than current methods. This unit can then be used in the synthesis of low bandgap materials via palladium-catalyzed coupling reactions.

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27

Berkaoui, M'Hamed, Francis Outurquin, and Claude Paulmier. "Acid catalyzed α-alkylation of β-aminothiophenes with aldehydes. synthesis of 2-alkyl 3-thiophenamines, bis(3-amino-2-thienyl)-methane derivatives and dithieno[3,2-b:2′,3′-e]pyridines." Journal of Heterocyclic Chemistry 33, no. 1 (January 1996): 9–16. http://dx.doi.org/10.1002/jhet.5570330103.

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28

Turner, Scott S., Joanna Daniell, Hiroki Akutsu, Peter N. Horton, Simon J. Coles, and Volker Schünemann. "New Spin-Crossover Compounds Containing the [Ni(mnt)] Anion (mnt = Maleonitriledithiolate)." Magnetochemistry 7, no. 5 (May 19, 2021): 72. http://dx.doi.org/10.3390/magnetochemistry7050072.

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Two novel salts containing the anion [Ni(mnt)2]− (mnt = maleonitriledithiolate) have been synthesized. The counter-ions, [Fe(II)(L1 or L2)2], are cationic complexes where L1 and L2 are methylated derivatives of 2,6-bis(pyazolyl)pyridine or pyrazine, which are similar to ligands found in a series of spin-crossover (SCO) complexes. Both salts are characterized by variable temperature single crystal X-ray diffraction and bulk magnetization measurements. Compound 1, [Fe(II)(L1)2][Ni(mnt)2]2 displays an incomplete and gradual SCO up to 300 K, followed by a more rapid increase in the high-spin fraction between 300 and 350 K. Compound 2, [Fe(II)(L2)2][Ni(mnt)2]2.MeNO2, shows a gradual, but more complete SCO response centered at 250 K. For compound 2, the SCO is confirmed by variable temperature Mössbauer spectroscopy. In both cases, the anionic moieties are isolated from each other and so no electrical conductivity is observed.

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29

Ivanova, Yulia B., Svetlana G. Puhovskaya, Nugzar Zh Mamardashvili, and Oscar I. Koifman. "SPECTROPHOTOMETRIC STUDY OF ACID-BASE PROPERTIES OF SPATIAL-DISTORTED DERIVATIVES OF PORPHYRINS IN ACETONITRILE." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENIY KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 59, no. 6 (July 12, 2018): 49. http://dx.doi.org/10.6060/tcct.20165906.5340k.

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Spectrophotometric titration method was used to study the acidic properties of: 5,10,15,20-tetrakis(thienyl-2-yl)-2,3,7,8,12,13,17,18-octaethylporphyrin (I), 5,10,15,20-tetrakis(4’-t-butylphenyl)-2,3,7,8,12,13,17,18-octaethylporphyrin (II), 5,10,15,20-tetrakis(3,5-di-t-butylphe-nyl)-2,3,7,8,12,13,17,18-octaethylporphyrin (III), 5,10,15,20-tetraphenyl-2,3,7,8,12,13,17,18-octaethylporphyrin (IV), 5,15-bis(4’-methoxyphenyl)-10,20-bis(4-nitro-phenyl)-2,8,12,18-tetrame-thyl-3,7,13,17-tetraarylporphyrin (V), 5,15-bis(4’-methoxyphenyl)-10,20-diphenyl-2,3,7,8,12,13, 17,18-octaethylporphyrin (VI), 5,15-bis(4’-methoxyphenyl)-2,8,12,18-tetramethyl-3,7,10,13,17,20-hexaethylporphin (VII), 5,10,15,20-tetrakis(4’-methoxyphenyl)-2,3,7,8,12,13,17,18-octaethylpor-phyrin (VIII) in the presence of a deprotonated agent, 1,8-diazabicyclo[5.4.0] undec-7-ene, in acetonitrile. Under deprotonation two families of spectral curves in the absorption spectra, having its own system of isobestic points, are formed. Electron absorption spectrum of molecular form transforms gradually into the spectrum of the final form of dianion with titrant concentration increase. Determination of the coordinates of the inflection (and the corresponding concentration of DBU) on the titration curve allowed us to distinguish two areas in the electron absorption spectra of the reaction system, which are likely belong to the first and second steps of deprotonation, namely, to the formation of mono- and dianionic forms (HP– and P2–) of the compound. Spectral characteristics of the ionized forms and combined ionization constant for the first and second steps (lgКа1 and lgКа2) were revealed. At the first step in the order of decreasing acidic properties of the ligands the compounds form a series of: III< V< VIII< VI < VII< II< IV < I; at the second step in decreasing order of the acidic properties of the ligands the compounds form a series of:.III < V < VI < II <VIII< VII < IV < I. The effect of structural and electronic properties of substituents on acid-base properties of porphyrins is analyzed. Thus, chemical modification of the macrocycle can lead to direct changes in acid-base properties of supramolecular macroheterocyclic ligands and can be a powerful tool to control the reactivity of compounds of the porphyrins class.

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30

Field, John S., Raymond J. Haines, Elena I. Lakoba, and M. Hal Sosabowski. "ChemInform Abstract: Novel Diphenylphosphine Derivatives of 2,2′-Bithiophene, 2,2′:5′,2′′-Terthiophene, 2-(2′-thienyl)pyridine and 2,6-Di-2′-thienylpyridine. Crystal Structures of 5,5′-Bis(diphenylphosphino)-2,2′-bithiophene, Diphenyl{5-[6′-(diphenylphosp." ChemInform 33, no. 15 (May 22, 2010): no. http://dx.doi.org/10.1002/chin.200215180.

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BERKAOUI, M., F. OUTURQUIN, and C. PAULMIER. "ChemInform Abstract: Acid Catalyzed α-Alkylation of β-Aminothiophenes with Aldehydes. Synthesis of 2-Alkyl-3-thiophenamines, Bis(3-amino-2- thienyl)methane Derivatives and Dithieno(3,2-b:2′,3′-e)pyridines." ChemInform 27, no. 30 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.199630090.

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Li, Jianmin, Xianping Deng, Zhiyong Zhang, Yafei Wang, Yu Liu, Keqi He, Ying Huang, Qiang Tao, Lixia Quan, and Weiguo Zhu. "Tuning photovoltaic performance of 9,9-dioctylfluorene-alt-5,7-bis(thiophen-2-yl)-2,3-biphenylthieno[3,4-b]pyrazine copolymeric derivatives by attaching additional donor units in pendant phenyl ring." Journal of Polymer Science Part A: Polymer Chemistry 50, no. 22 (August 17, 2012): 4686–94. http://dx.doi.org/10.1002/pola.26284.

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Li, Jianmin, Hua Tan, Fanyuan Meng, Wenhong Peng, Yafei Wang, Yu Liu, and Weiguo Zhu. "Synthesis and photovoltaic performance of N-dioctylmethyl-2,7-carbazole-alt-5,7-bis(thiophen-2-yl)-2,3-biphenylthieno[3,4-b] pyrazine copolymeric derivatives appending various donor units in phenyl moieties." Science China Chemistry 58, no. 2 (January 3, 2015): 301–8. http://dx.doi.org/10.1007/s11426-014-5284-7.

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Granifo, J. "Synthesis of mono- and binuclear triphenylphosphine complexes [{Mo(CO)3(PPh3)}n(dpp)] (n = 1,2; dpp = 2,3-bis(2-pyridyl)pyrazine) and the formation of heterobimetallic derivatives with Mo—dpp—M (M = Co, Ni) arrays." Polyhedron 13, no. 5 (January 1994): 713–16. http://dx.doi.org/10.1016/s0277-5387(00)81673-3.

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Diemer, Rolf, Uwe Dittes, Bernhard Nuber, Volker Seifried, Wolfgang Opferkuch, and Bernhard K. Keppler. "Synthesis, Characterization and Molecular Structures of some Bismuth(III) Complexes with Thiosemicarbazones and Dithiocarbazonic Acid Methylester Derivatives with Activity against Helicobacter Pylori." Metal-Based Drugs 2, no. 5 (January 1, 1995): 271–92. http://dx.doi.org/10.1155/mbd.1995.271.

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The reactions of bismuth(III) nitrate pentahydrate and bismuth(III) chloride with heterocyclic thiosemicarbazones and derivatives of dithiocarbazonic acid methylester were used to synthesize the respective bismuth(III) complexes, which could be divided into five groups D-H because of their stoichiometrical properties and their molecular structures. The molecular structure and the near coordination sphere of the bismuth(III) central atom of four representative compounds were determined by single-crystal X-ray studies. Bis[1-azepanyl-4-(2-pyridyl)-2,3-diazapenta-1,3-diene-1-thiolato-N′,N3,S]bismuth(III) nitrate (5) belongs to group D. The two tridentate ligands and the nitrate ion surround the bismuth atom. The best description of the coordination sphere appears to be that of a distorted trigonal dodecahedron with one position occupied by the lone pair of the bismuth atom. Bis[1-azepanyl-4-(2-thienyl)-2,3-diazapenta-1,3-diene-1-thiolato-N3,S]bismuth(III) nitrate (9) is assigned to complex type E. Here, two deprotonated ligand molecules are coordinated to the bismuth(III) central atom as bidentate ligands. The structure of this complex can best be described as a distorted trigonal antiprism with a five-coordinated central atom. The two triangular faces are formed by the atoms S(4), N(6), O(11) and S(3), N(4) and the lone pair of the central atom. The two chelate rings are almost perpendicular to each other. Complex molecules of group F form dimeric units with bichloro-bridged bismuth atoms. The structure of di-μ-chlorobis[1-azepanyl-4-(2-pyridyl)-2,3-diazapenta-1,3-diene-1-thiolato-N′,N3,S-chloro]dibismuth(III) (15) can be described as two six-coordinated bismuth atoms, which are bound together via two bridging chlorine atoms. The two bismuth atoms Bi(1) and Bi(1a) and the two bridging chlorine atoms Cl(2) and Cl(2a) form the Bi2Cl2 plane. The two tridentate ligand molecules coordinate via the same atoms as shown in complex 5. In addition, they form two parallel planes, which are perpendicular to the Bi2Cl2 plane. With regard to the center of the Bi(1)-Bi(2) axis they are central point symmetrical, i.e. one pyridine ring lies above and the other beneath the Bi2Cl2 plane. Bismuth(III) chloride and pyridine-2-carboxaldehydethiosemicarbazone 1 b or 2-acetylpyridine-thiosemicarbazone 1 c form complexes of group G. Three chlorine atoms and a bidentate ligand are coordinated to the bismuth(III) central atom. The bidentate ligand bound to the central atom through the N(3) atom and the sulfur atom of the thioketo group. The structure of 18 is completely different from the structures of the bismuth(III) complexes discussed so far and was therefore assigned to group H. The bismuth central atom is coordinated with two ligands, which are bound in different ways. One of them is deprotonated. This ligand is bound to the central atom via the sulfur atom S(3) of the thiolate group and the N(5) atom. An interaction between the sulfur atom of the thiophene ring and the bismuth atom is not possible.The other ligand molecule is not deprotonated. This ligand is bound to the bismuth(III) cation merely via the sulfur atom S(1) of the thioketo group. The best description of the coordination sphere of the bismuth atom is that of a distorted square bipyramidal polyhedron. The square face is formed by the atoms S(3), N(5), Cl(1), the lone pair and the bismuth atom within. The axial positions are occupied by the atoms S(1) and Cl(2). The bond angle between S(1), Bi(1) and Cl(2) differs by about eight degrees from the value determined for a regular square bipyramidal polyhedron of 180 degrees.Some of the newly synthesized bismuth complexes and three ligands have been tested against several strains of Helicobacter pylori bacteria in an agar dilution test. Almost all of the listed bismuth complexes show excellent inhibitory properties with regard to growth of H. pylori already at low concentrations.

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"Novel diphenylphosphine derivatives of 2,2′-bithiophene, 2,2′:5′,2″-terthiophene, 2-(2′-thienyl)pyridine and 2,6-di-2′-thienylpyridine. Crystal structures of 5,5′-bis(diphenylphosphino)-2,2′-bithiophene, diphenyl{5-[6′-(diphenylphosphino)-2′-pyridyl]-2-thienyl}phosphine and 2,6-bis[5′-(diphenylphosphino)-2′-thienyl]pyridine." Journal of the Chemical Society, Perkin Transactions 1, no. 24 (November 19, 2001): 3352–60. http://dx.doi.org/10.1039/b107389n.

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Reynolds, John R., Balasubramanian Sankaran, Gregory A. sotzing, David J. Irvin, Jennifer A. Irvin, Jerry L. Reddinger, and Shawn A. Sapp. "Electrochromic and Redox Electroactive Polymers Based on Ethylenedioxythiophene Derivatives." MRS Proceedings 413 (1995). http://dx.doi.org/10.1557/proc-413-373.

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ABSTRACTA family of electrically conductive polymers based on 3,4-ethylenedioxythiophene (EDOT) and its derivatives will be discussed as electrochromic and redox electroactive materials. Poly(alkylethylenedioxythiophenes), derivatized with octyl and tetradecyl pendant chains, exhibit significantly faster redox switching characteristics than the unsubstituted parent polymer. Bis(2-(3,4-ethylenedioxy)thienyl)arylene (BEDOT-Ar) and vinylene monomers electropolymerize at low potentials avoiding degradative side reactions. We outline the properties of EDOT polymers which exhibit low band gaps allowing for the formation of conductive complexes with a high degree of visible light transmission and show their electrochromic properties. The BEDOT-vinylene polymer, for example, has a band gap of 1.4 eV. A relatively high degree of electrochromic contrast is found at 600 nm as the polymers switch between insulating deep purple absorptive and conductive light blue states. Solid-state dual polymer electrochromic devices have been constructed using a combination of complementary anodically and cathodically coloring polymers based on the EDOT core.

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LADUREE, D., J. C. LANCELOT, M. ROBBA, E. CHENU, and G. MATHE. "ChemInform Abstract: Synthesis and Evaluation of Antileukemic Activity of 5-Thienyl- or 5-(2-Furyl)-2,3-dihydro-6,7-bis(hydroxymethyl)-1H-pyrrolizine Bis(alkylcarbamates) and Derivatives." ChemInform 20, no. 30 (July 25, 1989). http://dx.doi.org/10.1002/chin.198930174.

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