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Journal articles on the topic 'Thiophene synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 10 February 2022

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1

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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2

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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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

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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5

Irgashev, Roman A., Nadezhda S. Demina, and Gennady L. Rusinov. "Construction of 2,3-disubstituted benzo[b]thieno[2,3-d]thiophenes and benzo[4,5]selenopheno[3,2-b]thiophenes using the Fiesselmann thiophene synthesis." Organic & Biomolecular Chemistry 18, no. 16 (2020): 3164–68. http://dx.doi.org/10.1039/d0ob00300j.

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6

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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7

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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8

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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9

Madabhushi, Sridhar, Srinivas Kurva, Vinodkumar Sriramoju, Jagadeesh Babu Nanubolu та Suresh Reddy Cirandur. "Efficient synthesis of polyfunctionalized thiophene-2,3-diones and thiophen-3(2H)-ones using β-oxodithioesters". RSC Advances 5, № 79 (2015): 64797–801. http://dx.doi.org/10.1039/c5ra11629e.

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10

Ilhan, Koray T., Sebahat Topal, Mehmet S. Eroglu, and Turan Ozturk. "Concise synthesis of 3-alkylthieno[3,2-b]thiophenes; building blocks for organic electronic and optoelectronic materials." RSC Advances 9, no. 66 (2019): 38407–13. http://dx.doi.org/10.1039/c9ra08023f.

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Four step synthesis of 3-alkylthieno[3,2-b]thiophenes in the literature was reduced to two steps in good yields, through the preparation of the mono ketone, i.e. 1-(thiophene-3-ylthio)alkan-2-one, from 3-bromothiophene and ring formation reaction.

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11

Irgashev, Roman A., Nadezhda S. Demina, Polina E. Bayankina, Nikita A. Kazin, and Gennady L. Rusinov. "An Effective Route to Dithieno[3,2-b:2′,3′-d]thiophene-Based Hexaheteroacenes." Synlett 32, no. 10 (2021): 1009–13. http://dx.doi.org/10.1055/a-1398-7237.

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AbstractA series of 12H-[1]benzo[4′′,5′′]thieno[2′′,3′′:4′,5′]thieno[2′,3′:4,5]thieno[3,2-b]indoles were efficiently prepared in three steps starting from available benzo[b]thieno[2,3-d]thiophen-3(2H)-ones. These fused ketones were treated with the Vilsmeier reagent and hydroxylamine hydrochloride to give the corresponding 3-chlorobenzo[b]thieno[2,3-d]thiophene-2-carbonitriles, which then reacted with methyl sulfanylacetate to form methyl 3-aminobenzo[4′,5′]thieno[2′,3′:4,5]thieno[3,2-b]thiophene-2-carboxylates, in accordance with the Fiesselmann thiophene synthesis protocol. Finally, the desi

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12

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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13

Wang, Lin, Yu Jiao Xie, Xing Xing Zhang, and Jian She Hu. "Synthesis and Phase Behavior of a New Thiophene Monomer as Nematic Liquid Crystal." Advanced Materials Research 989-994 (July 2014): 185–88. http://dx.doi.org/10.4028/www.scientific.net/amr.989-994.185.

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The synthesis of a new liquid crystal thiophene monomer of (E)-4-(6-(3-(thiophen-3-yl)- acryloyloxy) hexyloxy) biphenyl-4’-ethylbenzoate (LC-M) is presented. The chemical structure of this monomer and intermediate compounds was characterized by FT-IR and1H-NMR. The phase behavior was investigated by polarizing optical microscopy and differential scanning calorimetry. LC-M showed nematic threaded and schlieren textures on heating and cooling cycles.

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14

Furuyama, Taniyuki, Daiki Noguchi, Yuta Suzuki, and Nagao Kobayashi. "Synthesis and characterization of aza-bridged thiophene–pyrrole dyads and their isomers." Canadian Journal of Chemistry 92, no. 8 (2014): 765–70. http://dx.doi.org/10.1139/cjc-2014-0039.

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Aza-bridged thiophene-pyrrole dyads were synthesized and characterized. Thiophenes substituted with electron-withdrawing groups (EWGs) were used as building blocks for the framework. However, an unprecedented cyclization occurred, and a thieno[2,3-d]pyrimidine derivative (4) was obtained in the reaction between 2,5-diamino-3,4-dicyanothiophene (1) and 3,5-diiminoisoindoline (3), whereas the reaction between 2,5-diamino-3,4-dicarboxylic acid ethyl ester (2) and 3 produced the desired dyad (5). The structures of 4 and 5 were unambiguously characterized by X-ray diffraction. Compound 5 is the fir

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15

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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16

Puciová, Monika, Peter Ertl, and Štefan Toma. "Synthesis of Ferrocenyl-Substituted Heterocycles: The Beneficial Effect of the Microwave Irradiation." Collection of Czechoslovak Chemical Communications 59, no. 1 (1994): 175–85. http://dx.doi.org/10.1135/cccc19940175.

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The synthesis of ferrocenyl-substituted thiophenes, furans, pyrroles, pyrimidine and pyrazole has been studied. 2-Ferrocenylpyrroles were prepared from ferrocenyl ketoximes and acetylene in DMSO - KOH mixture whereas 3-chloro-3-ferrocenylacrylaldehydes and thioglycolic or glycolic acids were the starting materials for the synthesis of the thiophene and furan derivatives. The yields were significantly enhanced when the reactions were carried out in a microwave oven. The lower stability of 2-ferrocenylfuran in comparison with 2-ferrocenylthiophene is discussed on the basis of semiempirical quant

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17

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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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

Lee, Sang Bok, and Jong-In Hong. "A facile and convenient synthesis of 2-(arylthio)thiophenes, 2-(alkylthio)thiophene, and 2-(thiophenylthio)thiophene." Tetrahedron Letters 36, no. 46 (1995): 8439–42. http://dx.doi.org/10.1016/0040-4039(95)01816-z.

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20

Wang, Dai Fu, Hui Gao, Xiao Hong Tan, et al. "Facile Synthesis and Crystal Structure of N-(3-Cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-2,2,2-trifluoroacetamide." Advanced Materials Research 887-888 (February 2014): 661–64. http://dx.doi.org/10.4028/www.scientific.net/amr.887-888.661.

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N-(3-Cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-2,2,2-trifluoroacetamide was synthesized by the acylation reaction of trifluoroacetic anhydride with 2-amino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carbonitrile, which was prepared via microwave-assisted Gewald reaction with K2CO3 as a heterogeneous solid base catalyst. This protocol presented such advantages as short reaction time, high yield, easy work-up and environmentally benign procedures. The structure of the title compound was confirmed by IR, 1H NMR, MS, elemental analysis and X-ray single-crystal diffraction method. X-Ray diffractio

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21

Gentle, T. M., C. T. Tsai, K. P. Walley, and A. J. Gellman. "Surface synthesis of thiophene." Catalysis Letters 2, no. 1 (1989): 19–26. http://dx.doi.org/10.1007/bf00765326.

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22

Kabirifard, Hassan, Pardis Hafez Taghva, Hossein Teimouri, et al. "Synthesis of Organic Ligands via Reactions of 4-Benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione with N-Nucleophiles." Heteroatom Chemistry 2020 (July 8, 2020): 1–9. http://dx.doi.org/10.1155/2020/5945796.

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The reaction of 4-benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione (1) with aminoheteroaryls, lamotrigine, 1,3-diaminoheteroaryls, dapsone, NH2R (hydroxylamine, DL-1-phenylethylamine, and metformin), and 4,4′-bipyridine in THF/H2O (1 : 1) at room temperature led to 3-N-phenylthiocarbamoyl-2-butenamides 2–5, while that with naphthylamines and 1,3-phenylenediamine in ethanol at high temperature led to 5-phenylamino-2,5-dihydrothiophene-2-ones 6–8 as organic ligands in the medium to good yields. These showed the nucleophilic attacks of N-nucleophiles, except primary aromatic amines, on thioes

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23

Xiao, Guo Yong, Xiao Li, Hai Jun Chi, Yun Hua Lu, Zhi Zhi Hu, and Jiang Long Yu. "Synthesis and Photophysical Properties of Red-Emitting Iridium （Ⅲ） Complex Bearing Benzothiazole." Advanced Materials Research 399-401 (November 2011): 1131–34. http://dx.doi.org/10.4028/www.scientific.net/amr.399-401.1131.

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New red phosphorescent material, (E)-2-(2-(thiophen-2-yl) vinyl)benzothiazole(2THSBT) iridium(III) acetylacetone(acac) complex [(2THSBT)2Ir(acac)] is synthesized from 2-methyl benzothiazole, thiophene-2-carbaldehyde and iridium trichloride anhydrate. The complex is characterized by MS and 1H-NMR. (2THSBT)2Ir(acac) gives a photoluminescence at 687nm, phosphorescent quantum yield: Φ(2THSBT)2Ir(acac)=0.2 and EHOMO = -4.8 eV, ELUMO = -2.6eV, respectively. The complex may be a promising electrophosphorescent material.

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24

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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25

Yilmaz, Fatih. "Synthesis and Characterisation of Some New Hybrid Molecules Containing Thiophene, Triazole and Coumarin Rings under Microwave Conditions." Journal of Chemical Research 42, no. 7 (2018): 361–65. http://dx.doi.org/10.3184/174751918x15314831778603.

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In this work, a new series of N‘-{[4-amino-5-oxo-3-(thiophen-2-yl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetyl}-2-oxo-2H-1-benzopyran-3-carbohydrazides (thiophene–triazole–coumarin hybrid molecules) was synthesised from the reaction of 2-[4-amino-5-oxo-3-(thiophen-2-yl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetohydrazide and 3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromen-2-ones by using microwave irradiation and conventional heating procedures and their results were compared. The reaction was performed using a very small amount of organic solvent and without using a catalyst.

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26

Joule, John A. "Thiophenes from Viktor Meyer to Poly(Thiophene) Some Reactions and Synthesis." Phosphorus, Sulfur, and Silicon and the Related Elements 188, no. 4 (2013): 287–316. http://dx.doi.org/10.1080/10426507.2012.736892.

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27

Cikotiene, I., R. Sazinas, R. Mazeikaite, and L. Labanauskas. "Synthesis of Fused Thiophene-Isoxazoles from 2-Alkynyl-3-Nitro-Thiophenes." Synfacts 2011, no. 02 (2011): 0140. http://dx.doi.org/10.1055/s-0030-1259381.

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28

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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29

Elgemeie, G. H., K. A. Ahmed, E. A. Ahmed, M. H. Helal, and D. M. Masoud. "Synthesis of novel tetrasubstituted thiophenes based dye using sodium a-cyanoketene dithiolates as starting materials." Pigment & Resin Technology 44, no. 6 (2015): 339–46. http://dx.doi.org/10.1108/prt-12-2014-0117.

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Purpose – The study aims to synthesise new thiophene-based dyes by an efficient method using sodium a-cyanoketene dithiolates as starting components for synthesis of tetra-substituted thiophenes, which act as a coupler for the synthesised dye. The synthesised dyes are applied for printing polyamide and polyester fabrics using the screen printing technique. Design/methodology/approach – Treatment of 1 with carbon disulfide in alkaline medium forming disodium salt 2, which act as starting point for heterocyclisation to prepare these dye stuff 7. Sodium a-cyanoketene dithiolates 2 react with two

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30

LEE, S. B., and J. I. HONG. "ChemInform Abstract: A Facile and Convenient Synthesis of 2-(Arylthio)thiophenes, 2-( Alkylthio)thiophene, and 2-(Thiophenylthio)thiophene." ChemInform 27, no. 9 (2010): no. http://dx.doi.org/10.1002/chin.199609120.

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31

Ateş, Esin, Nilgün Kizilcan, and Merve İstif. "New comonomer synthesis from thiophene-2-carbonyl chloride and cyclohexanone formaldehyde resin." Pigment & Resin Technology 44, no. 2 (2015): 79–86. http://dx.doi.org/10.1108/prt-10-2013-0091.

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Purpose – The purpose of this paper is to synthesise an electro-active monomer containing ketonic resins and then to investigate the redox reaction between Fe+3 and bound thiophene in comonomer. First, thiophene-functionalised ketonic resins were synthesised by esterification reaction of thiophene-2-carbonyl chloride (ThCCl) and hydroxyl groups of cyclohexanone formaldehyde resin (CFR). Thiophene-containing cyclohexanone formaldehyde resin (Th-CFR) was then polymerised by ferric salt. The structures of the specimens were characterised by means of Fourier transform infrared and Proton – Nuclear

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32

Martinez, F., R. Voelkel, D. Naegele, and H. Naarmann. "Thiophene Oligomers: Synthesis and Characterization." Molecular Crystals and Liquid Crystals Incorporating Nonlinear Optics 167, no. 1 (1989): 227–32. http://dx.doi.org/10.1080/00268948908037179.

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33

Elgemeie, Galal H., Wafaa A. Zaghary, Kamelia M. Amin, and Tamer M. Nasr. "First Synthesis of Thiophene Thioglycosides." Journal of Carbohydrate Chemistry 28, no. 3 (2009): 161–78. http://dx.doi.org/10.1080/07328300902789209.

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34

Eller, Christina, Gerald Kehr, Constantin G. Daniliuc, Douglas W. Stephan, and Gerhard Erker. "Thiophene synthesis via 1,1-carboboration." Chemical Communications 51, no. 33 (2015): 7226–29. http://dx.doi.org/10.1039/c5cc01806d.

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Reaction of bis(tert-butylethynyl)sulfide with the boron Lewis acid reagents X–B(C<sub>6</sub>F<sub>5</sub>)<sub>2</sub> (X = CH<sub>3</sub>, Cl, C<sub>6</sub>F<sub>5</sub>) in pentane at r.t. gave the respective borylated thiophenes in a sequence of 1,1-carboboration reactions.

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Li, Jing Tong, Ran Sheng Liu, Zeng Dian Zhao, and Ru Jun Yu. "Synthesis and Characterization of a Novel Diphenylamine-Thiophene Compound for Blue Organic Light-Emitting Diodes." Advanced Materials Research 893 (February 2014): 747–50. http://dx.doi.org/10.4028/www.scientific.net/amr.893.747.

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Diphenylamine and thiophene compounds are promising materials for organic light-emitting diodes (OLEDs). We report here, the synthesis and optical property of a novel small molecular weight derivative,N4.N4,N4'.N4'-tetrakis (4- (thiophen-2-yl) phenyl)-[1,1'-bipheny-4,4'-diamine (TPPA). The target molecule was synthesized using 4,4'-dibromobiphenyl as the starting material, and the proceeding reactions included bromination, Buchwald and Suzuki coupling reactions. According to the optical characterization of it, the absorption peak and excitation peak is at 351nm and 412 nm, respectively. The lu

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Wei, Cui Liu, Xiao Ping Zou, Jin Cheng, et al. "Carbon Nanotubes Grown by Ethanol Catalytic Combustion with an Additive of Thiophene." Advanced Materials Research 123-125 (August 2010): 627–30. http://dx.doi.org/10.4028/www.scientific.net/amr.123-125.627.

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Combustion method is a simple method to synthesize carbon nanotubes(CNTs), which employs flames of carbon-contained reactant to synthesize CNTs. It has been proved that combustion method is an effective method to synthesize carbon nanotubes and carbon nanofibers. In this paper, we reported the synthesis of CNTs by using ethanol catalytic combustion with an additive of thiophene, which employed ethanol as carbon source and fuel, nitrate as catalyst precursor, stainless steel as substrate, and thiophene as accelerant. Compared with previous reports on the synthesis of CNTs by ethanol catalytic c

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Vrábel, Viktor, Július Sivý, Peter Šafář, and Štefan Marchalín. "Electronic structure, novel synthesis, and O—H...O and C—H...O interactions in two 6-oxopiperidine-2-carboxylic acid derivatives." Acta Crystallographica Section C Structural Chemistry 70, no. 8 (2014): 817–22. http://dx.doi.org/10.1107/s2053229614016301.

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Molecules of (S)-6-oxo-1-(thiophen-2-ylmethyl)piperidine-2-carboxylic acid, C11H13NO3S, crystallize as single enantiomers in the space groupP21and the thiophene ring is disordered over two positions, while (S)-6-oxo-1-(thiophen-3-ylmethyl)piperidine-2-carboxylic acid, C11H13NO3S, crystallizes as a single enantiomer in the space groupP212121. Their absolute configurations were confirmed by anomalous dispersion effects in diffraction measurements on the crystals. The molecules of each compound are linked by a combination of strong O—H...O hydrogen bonds and weak C—H...O interactions, resulting i

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Seyler, Helga, Stefan Haid, Tae-Hyuk Kwon, et al. "Continuous Flow Synthesis of Organic Electronic Materials – Case Studies in Methodology Translation and Scale-up." Australian Journal of Chemistry 66, no. 2 (2013): 151. http://dx.doi.org/10.1071/ch12406.

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The continuous flow synthesis of functional thiophene derivatives was examined. Methodology for the lithiation of thiophene building blocks was developed using a commercial bench-top flow reactor. In addition, the advantages of flow processing were demonstrated in the synthesis of a high performance organic dye in gram scale.

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39

Wardakhan, Wagnat Wahba, El-Sayed Nahed Nasser Eid, and Rafat Milad Mohareb. "Synthesis and anti-tumor evaluation of novel hydrazide and hydrazide-hydrazone derivatives." Acta Pharmaceutica 63, no. 1 (2013): 45–57. http://dx.doi.org/10.2478/acph-2013-0004.

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The reaction of cyclopentanone with cyanoacetylhydrazine gave 2-cyano-2-cyclopentylideneacetohydrazide (1). Treatment of compound 1 with elemental sulphur in the presence of triethylamine afforded 2-amino-5,6-dihydro- -4H-cyclopenta[b]thiophene-3-carbohydrazide (2), which in-turn formed the corresponding intermediate diazonium salt. The latter was coupled with either ethyl cyanoacetate or ethyl acetoacetate to form 2-cyano-2-(3-(hydrazinecarbonyl)- 5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl)hydrazono) acetate (3) and ethyl 2-(2-(3-(hydrazinecarbonyl)-5,6-dihydro- 4H-cyclopenta[b]thiophen-2-yl)h

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40

Protiva, Jiří, Jaroslav Pecka, Jiří Urban, and Jiří Zima. "Synthesis of 20-iodoeicosanoic and 20-[125I]-iodoeicosanoic acids." Collection of Czechoslovak Chemical Communications 55, no. 6 (1990): 1546–54. http://dx.doi.org/10.1135/cccc19901546.

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20-Iodoeicosanoic acid (X) was prepared in 9 steps, its carbon chain being constructed from thiophene and ethyl ester chlorides of dodecanedioic and butanedioic acids. Isotope exchange afforded 20-[125I]-iodoeicosanoic acid required for scintigraphic studies of the myocardium. Desulfuration of the thiophene precursor VIII was accompanied by formation of side products XI-XIX arising by cleavage of the thiophene C-C bonds. Desulfuration of the model compounds XX and XXI has shown that the formation of these products is general.

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41

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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Osadnik, Andreas, and Arne Lützen. "Synthesis of functionalized thiophene/phenyl co-oligomers by direct arylation of thiophenes." Arkivoc 2015, no. 2 (2014): 40–51. http://dx.doi.org/10.3998/ark.5550190.p008.833.

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Bauer, Matthias, Maike Tünnermann, Pia Rehsies, and Ulrich Flörke. "A Straightforward Synthesis to Novel 1,10-Phenanthrolines with Fused Thiophene Structure." Synlett 29, no. 20 (2018): 2638–42. http://dx.doi.org/10.1055/s-0037-1611022.

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We report here a straightforward synthesis for a series of new structures with fused 1,10-phenanthroline-thiophene connection. They are synthesized with a modified Hinsberg thiophene procedure, followed by successive modification to yield several 5,7-disubstituted thieno[3,4-f][1,10]phenanthrolines, most notable thiophene-substituted compounds that could be potentially of use for organic electronics applications. For some selected examples, crystal structures were obtained, showing a nearly coplanar arrangement around the fused connection, also beneficial for an effective electron transfer i

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Casey, Abby, Yang Han, Mark F. Wyatt, Thomas D. Anthopoulos, and Martin Heeney. "Novel soluble thieno[3,2-b]thiophene fused porphyrazine." RSC Advances 5, no. 110 (2015): 90645–50. http://dx.doi.org/10.1039/c5ra17859b.

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Medvedev, Jury J., Ilya V. Efimov, Yuri M. Shafran, Vitaliy V. Suslonov, Vasiliy A. Bakulev та Valerij A. Nikolaev. "Rh(II)-mediated domino [4 + 1]-annulation of α-cyanothioacetamides using diazoesters: A new entry for the synthesis of multisubstituted thiophenes". Beilstein Journal of Organic Chemistry 13 (30 листопада 2017): 2569–76. http://dx.doi.org/10.3762/bjoc.13.253.

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A new approach towards the synthesis of multisubstituted thiophenes is elaborated based on Rh(II)-catalyzed domino reactions of acyclic diazoesters with α-cyanothioacetamides. It provides a way for the preparation of 5-amino-3-(alkoxycarbonylamino)thiophene-2-carboxylates, 2-(5-amino-2-methoxycarbonylthiophene-3-yl)aminomalonates and (2-cyano-5-aminothiophene-3-yl)carbamates with the preparative yields of up to 67%. It was also shown that α-cyanothioacetamides easily interact with dirhodium carboxylates to give rather stable 2:1 complexes, resulting in an evident decrease in the efficiency of

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46

Tovar, John, Reid Messersmith, and Maxime Siegler. "A Heptacyclic Heptacycle: A Doubly Naphtho[b]thiophene Fused Borepin." Synlett 29, no. 19 (2018): 2499–502. http://dx.doi.org/10.1055/s-0037-1610163.

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The synthesis and characterization of a doubly naphtho[b]thiophene fused borepin is reported herein, and the properties are compared to smaller benzo[b]thiophene and thiophene fused borepins. The synthesis involved the preparation of a symmetrical disubstituted alkyne that was reduced to a Z-olefin. This was followed by borepin formation from the alkene directly by way of thieno dilithiation. The electronic properties are consistent with extended benzannulation of the smaller analogues, and the enhancement of the brickwork type stacking is apparent as planar aromatic wings are extended from th

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47

Nedolya, Nina, Boris Trofimov, Olga Tarasova, and Alexander Albanov. "Expeditious Scalable Catalyst-Free One-Pot Synthesis of 4-Alkoxy-5-amino-3-methylthiophene-2-carbonitriles via Sequential Reactions of Lithiated Alkoxyallenes with Isothiocyanates and 2-Bromoacetonitrile." Synthesis 50, no. 09 (2018): 1891–900. http://dx.doi.org/10.1055/s-0036-1591905.

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A synthetically simple and convenient approach to tetrasubstituted thiophenes with rare combination of the alkoxy, amino, and cyano groups has been developed. The assembly of polyfunctionalized thiophene ring is implemented in one preparative step by sequential addition of isothiocyanate and 2-bromoacetonitrile to the lithiated (with n-BuLi) alkoxyallene. The reaction proceeds through in situ formation and intramolecular cyclization of cyanomethyl 2-alkoxy-N-buta-2,3-dienimidothioate (1-aza-1,3,4-triene).

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48

Abomelha, Hanna. "Synthesis of novel dyes based on thiophene analogues with antibacterial activity for dyeing polyester fabrics." Pigment & Resin Technology 48, no. 4 (2019): 337–47. http://dx.doi.org/10.1108/prt-02-2018-0012.

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Purpose This study aims to the synthesis of some novel 4-arylazo-3-hydroxythiophene analogues containing sulphapyridine and sulphathiazole dyestuffs and studying their application in dyeing polyester fabrics and rendering their antibacterial efficacy. Design/methodology/approach Simultaneous dyeing and antibacterial finishing for polyester fabric using a new antibacterial disperse dye having a modified chemical structure to thiophene dyes were studied. Construction of the thiophene dyes was carried out by diazo-coupling of diazotized sulphonamide-containing heterocyclic rings sulphapyridine an

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Xue, Li-Ping, Zhao-Hao Li, Lu-Fang Ma, and Li-Ya Wang. "Crystal engineering of cadmium coordination polymers decorated with nitro-functionalized thiophene-2,5-dicarboxylate and structurally related bis(imidazole) ligands with varying flexibility." CrystEngComm 17, no. 33 (2015): 6441–49. http://dx.doi.org/10.1039/c5ce01248a.

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Five bis(imidazole) ligand modulated cadmium coordination polymers based on a new nitro-functionalized thiophene-2,5-dicarboxylate ligand or 4-nitro-thiophene-2-carboxylic acid involving in situ ligand synthesis.

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Shono, Keisuke, Yugo Sumino, Shota Tanaka, Shunsuke Tamba, and Atsunori Mori. "Polythiophene synthesis via halogen dance." Org. Chem. Front. 1, no. 6 (2014): 678–82. http://dx.doi.org/10.1039/c4qo00109e.

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