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Journal articles on the topic 'Terthiophenes'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Vallan, Lorenzo, Emin Istif, I. Jénnifer Gómez, Nuria Alegret, and Daniele Mantione. "Thiophene-Based Trimers and Their Bioapplications: An Overview." Polymers 13, no. 12 (June 16, 2021): 1977. http://dx.doi.org/10.3390/polym13121977.

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Certainly, the success of polythiophenes is due in the first place to their outstanding electronic properties and superior processability. Nevertheless, there are additional reasons that contribute to arouse the scientific interest around these materials. Among these, the large variety of chemical modifications that is possible to perform on the thiophene ring is a precious aspect. In particular, a turning point was marked by the diffusion of synthetic strategies for the preparation of terthiophenes: the vast richness of approaches today available for the easy customization of these structures allows the finetuning of their chemical, physical, and optical properties. Therefore, terthiophene derivatives have become an extremely versatile class of compounds both for direct application or for the preparation of electronic functional polymers. Moreover, their biocompatibility and ease of functionalization make them appealing for biology and medical research, as it testifies to the blossoming of studies in these fields in which they are involved. It is thus with the willingness to guide the reader through all the possibilities offered by these structures that this review elucidates the synthetic methods and describes the full chemical variety of terthiophenes and their derivatives. In the final part, an in-depth presentation of their numerous bioapplications intends to provide a complete picture of the state of the art.

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2

Burrell, A. K., J. Chen, G. E. Collis, D. K. Grant, D. L. Officer, C. O. Too, and G. G. Wallace. "Functionalised poly(terthiophenes)." Synthetic Metals 135-136 (April 2003): 97–98. http://dx.doi.org/10.1016/s0379-6779(02)00865-2.

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3

Jayasuriya, Nimal, Jacques Kagan, John E. Owens, Eugene P. Kornak, and Daniel M. Perrine. "Photocyclization of terthiophenes." Journal of Organic Chemistry 54, no. 17 (August 1989): 4203–5. http://dx.doi.org/10.1021/jo00278a039.

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4

Nakayama, Juzo, Yoichi Nakamura, Takayuki Tajiri, and Masamatsu Hoshino. "Preparation of Naturally Occurring a-Terthiophenes (2,2':5',2''-Terthiophenes)." HETEROCYCLES 24, no. 3 (1986): 637. http://dx.doi.org/10.3987/r-1986-03-0637.

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5

Chen, J., G. Tsekouras, D. L. Officer, P. Wagner, C. Y. Wang, C. O. Too, and G. G. Wallace. "Novel fullerene-functionalised poly(terthiophenes)." Journal of Electroanalytical Chemistry 599, no. 1 (January 2007): 79–84. http://dx.doi.org/10.1016/j.jelechem.2006.09.007.

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6

Chahma, M'hamed, Christopher D. McTiernan, and Sara A. Abbas. "Characterization of phenomena occurring at the interface of chiral conducting surfaces." New J. Chem. 38, no. 8 (2014): 3379–85. http://dx.doi.org/10.1039/c4nj00489b.

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7

Wagner, Pawel, Ashton C. Partridge, Kenneth W. Jolley, and David L. Officer. "Facile synthesis of acetylene-substituted terthiophenes." Tetrahedron Letters 48, no. 36 (September 2007): 6245–48. http://dx.doi.org/10.1016/j.tetlet.2007.07.032.

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8

Chen, Li, Jian P. Gong, Yutaka Ohsedo, and Yoshihito Osada. "Water-Swollen Hydrogels with Pendant Terthiophenes." Macromolecular Chemistry and Physics 204, no. 4 (March 2003): 661–65. http://dx.doi.org/10.1002/macp.200390034.

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9

Stepp, Brian R., and SonBinh T. Nguyen. "Enhancement of the Physical Properties of Poly((2-terthiophenyl)norbornene) through Cross-Linking Pendant Terthiophenes." Macromolecules 37, no. 22 (November 2004): 8222–29. http://dx.doi.org/10.1021/ma035740h.

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10

Noh, Hui-Bog, and Yoon-Bo Shim. "Catalytic activity of polymerized self-assembled artificial enzyme nanoparticles: applications to microfluidic channel-glucose biofuel cells and sensors." Journal of Materials Chemistry A 4, no. 7 (2016): 2720–28. http://dx.doi.org/10.1039/c5ta08823b.

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11

Wurzbach, Iris, Christian Rothe, Kirsten Bruchlos, Sabine Ludwigs, and Frank Giesselmann. "Shear alignment and 2D charge transport of tilted smectic liquid crystalline phases – XRD and FET studies." Journal of Materials Chemistry C 7, no. 9 (2019): 2615–24. http://dx.doi.org/10.1039/c8tc04536d.

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In the tilted smectic phases of terthiophenes, shear alignment macroscopically aligns the tilt direction of the director leading to a substantial in-plane anisotropy of charge carrier mobility in organic field effect transistor (OFET) experiments.

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12

Inoue, Shinobu, Shoji Nishiguchi, Satoshi Murakami, Yoshio Aso, Tetsuo Otsubo, Volkmar Vill, Akira Mori, and Seiji Ujiie. "Hexakis(terthiophenylthio)benzene as a Mew Class Liquid Crystalline Molecule." Journal of Chemical Research 23, no. 10 (October 1999): 596–97. http://dx.doi.org/10.1177/174751989902301005.

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A disk-like molecule, in which six α-linked terthiophenes are connected to a central benzene core via a thioether linkage, shows a sequence of calamitic liquid crystalline mesomorphism involving smectic C, smectic A and nematic phases.

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13

DiCésare, Nicolas, Michel Belletête, Claudio Marrano, Mario Leclerc, and Gilles Durocher. "Intermolecular Interactions in Conjugated Oligothiophenes. 1. Optical Spectra of Terthiophene and Substituted Terthiophenes Recorded in Various Environments." Journal of Physical Chemistry A 103, no. 7 (February 1999): 795–802. http://dx.doi.org/10.1021/jp983186l.

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14

Gordon, K. C., T. M. Clarke, D. L. Officer, S. B. Hall, G. E. Collis, and A. K. Burrell. "Vibrational Spectra and Calculations on Substituted Terthiophenes." Synthetic Metals 137, no. 1-3 (April 2003): 1367–68. http://dx.doi.org/10.1016/s0379-6779(02)01066-4.

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15

Wagner, Pawel, and David L. Officer. "Structural and electronic properties of substituted terthiophenes." Synthetic Metals 154, no. 1-3 (September 2005): 325–28. http://dx.doi.org/10.1016/j.synthmet.2005.07.082.

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16

Mitsudo, Koichi, Hidehiko Sato, Arata Yamasaki, Natsuyo Kamimoto, Jun Goto, Hiroki Mandai, and Seiji Suga. "Synthesis and Properties of Ethene-Bridged Terthiophenes." Organic Letters 17, no. 19 (September 18, 2015): 4858–61. http://dx.doi.org/10.1021/acs.orglett.5b02417.

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17

Hudson, J. B., L. Harris, R. J. Marles, and J. T. Arnason. "THE ANTI-HIV ACTIVITIES OF PHOTOACTIVE TERTHIOPHENES." Photochemistry and Photobiology 58, no. 2 (August 1993): 246–50. http://dx.doi.org/10.1111/j.1751-1097.1993.tb09556.x.

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18

DiCésare, Nicolas, Michel Belletête, Mario Leclerc, and Gilles Durocher. "Intermolecular Interactions in Conjugated Oligothiophenes. 2. Quantum Chemical Calculations Performed on Crystalline Structures of Terthiophene and Substituted Terthiophenes." Journal of Physical Chemistry A 103, no. 7 (February 1999): 803–11. http://dx.doi.org/10.1021/jp983187d.

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19

Svedberg, Fredrik, Yury Alaverdyan, Patrik Johansson, and Mikael Käll. "Raman Spectroscopic Studies of Terthiophenes for Molecular Electronics." Journal of Physical Chemistry B 110, no. 51 (December 2006): 25671–77. http://dx.doi.org/10.1021/jp062577u.

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20

Areephong, Jetsuda, Tibor Kudernac, Jaap J. D. de Jong, Gregory T. Carroll, Davide Pantorott, Johan Hjelm, Wesley R. Browne, and Ben L. Feringa. "On/Off Photoswitching of the Electropolymerizability of Terthiophenes." Journal of the American Chemical Society 130, no. 39 (October 2008): 12850–51. http://dx.doi.org/10.1021/ja803714p.

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21

Liedberg, B., Z. Yang, I. Engquist, M. Wirde, U. Gelius, G. Götz, P. Bäuerle, R. M. Rummel, Ch Ziegler, and W. Göpel. "Self-Assembly of α-Functionalized Terthiophenes on Gold." Journal of Physical Chemistry B 101, no. 31 (July 1997): 5951–62. http://dx.doi.org/10.1021/jp970229+.

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22

Komatsu, K., D. Yamazaki, T. Nishinaga, and N. Tanino. "Bent Radical Cation Dimers from Bicyclooctene-Substituted Terthiophenes." Synfacts 2007, no. 1 (January 2007): 0041. http://dx.doi.org/10.1055/s-2006-955676.

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23

Zanardi, Chiara, Roberta Scanu, Laura Pigani, Maria I. Pilo, Gavino Sanna, Renato Seeber, Nadia Spano, Fabio Terzi, and Antonio Zucca. "Synthesis and electrochemical polymerisation of 3′-functionalised terthiophenes." Electrochimica Acta 51, no. 23 (June 2006): 4859–64. http://dx.doi.org/10.1016/j.electacta.2006.01.025.

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24

Vélez, J. H., F. R. Díaz, M. A. del Valle, J. C. Bernède, and G. A. East. "Synthesis of 3′,4′-disubstituted terthiophenes. Characterization and electropolymerization. I. 3′,4′-dibromo-2,2′:5′,2″-terthiophene in photovoltaic display." Journal of Applied Polymer Science 102, no. 6 (2006): 5314–21. http://dx.doi.org/10.1002/app.24865.

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25

Grant, D. K., D. L. Officer, and A. K. Burrell. "Synthesis and polymerisation of fully conjugated polyether-substituted terthiophenes." Synthetic Metals 135-136 (April 2003): 103–4. http://dx.doi.org/10.1016/s0379-6779(02)00873-1.

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26

Watson, Keith J., Patrick S. Wolfe, SonBinh T. Nguyen, Jin Zhu, and Chad A. Mirkin. "Norbornenyl-Substituted Thiophenes and Terthiophenes: Novel Doubly Polymerizable Monomers." Macromolecules 33, no. 13 (June 2000): 4628–33. http://dx.doi.org/10.1021/ma992035t.

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27

Hudson, J., E. Graham, R. Rossi, A. Carpita, D. Neri, and G. H. Towers. "Biological Activities of Terthiophenes and Polyynes from the Asteraceae." Planta Medica 59, no. 05 (October 1993): 447–50. http://dx.doi.org/10.1055/s-2006-959729.

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28

Stanforth, Stephen P. "Semi-empirical evaluation of substituted terthiophenes as polythiophene precursors." Journal of Heterocyclic Chemistry 36, no. 1 (January 1999): 137–40. http://dx.doi.org/10.1002/jhet.5570360120.

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29

Mitsudo, Koichi, Hidehiko Sato, Arata Yamasaki, Natsuyo Kamimoto, Jun Goto, Hiroki Mandai, and Seiji Suga. "ChemInform Abstract: Synthesis and Properties of Ethene-Bridged Terthiophenes." ChemInform 47, no. 7 (January 2016): no. http://dx.doi.org/10.1002/chin.201607133.

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30

Breuer, Natascha, and Thomas J. J. Müller. "Synthesis and electronic properties of 5,5″-diacceptor substituted terthiophenes." Dyes and Pigments 149 (February 2018): 676–85. http://dx.doi.org/10.1016/j.dyepig.2017.11.038.

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31

Nakayama, Juzo, Yo Ting, Yoshiaki Sugihara, and Akihiko Ishii. "Synthesis of Highly Congested BI- and Terthiophenes; 3,4,3',4'-Tetra-tert-butylbithiophene and 3',4'-Di-tert-butyl-2,2':5'2''-terthiophene." HETEROCYCLES 44, no. 1 (1997): 75. http://dx.doi.org/10.3987/com-96-s11.

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32

Okujima, Tetsuo, Akiko Toda, Yoko Miyashita, Ayumi Nonoshita, Hiroko Yamada, Noboru Ono, and Hidemitsu Uno. "SYNTHESIS AND PROPERTIES OF AZULENE-SUBSTITUTED THIOPHENES, TERTHIOPHENES AND DITHIENOTHIOPHENES." HETEROCYCLES 86, no. 1 (2012): 637. http://dx.doi.org/10.3987/com-12-s(n)63.

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33

Wagner, Paweł, David L. Officer, and Maciej Kubicki. "Flip-type disorder in 3-substituted 2,2′:5′,2′′-terthiophenes." Acta Crystallographica Section C Crystal Structure Communications 63, no. 7 (June 14, 2007): o400—o404. http://dx.doi.org/10.1107/s0108270107024699.

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34

Scheuble, Martin, Miriam Goll, and Sabine Ludwigs. "Branched Terthiophenes in Organic Electronics: From Small Molecules to Polymers." Macromolecular Rapid Communications 36, no. 2 (November 29, 2014): 115–37. http://dx.doi.org/10.1002/marc.201400525.

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35

Sears, Wendy A., Craig D. MacKinnon, Robert C. Mawhinney, Lauren C. Sinnemaki, Matthew J. Johnson, A. John Winter, and Craig M. Robertson. "Using the nitro group to induce π-stacking in terthiophenes." Canadian Journal of Chemistry 88, no. 4 (April 2010): 309–17. http://dx.doi.org/10.1139/v09-165.

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A new synthetic route to mononitrated oligothiophenes is described, as well as the preparation of halogenated derivatives (Br, I) thereof. An unusual deep red colour is observed and explained, with the aid of DFT calculations, as arising from a significant quinoidal contribution to the molecular structure. The crystal structures of two compounds, H(C4H2S)3NO2 and Br(C4H2S)3NO2, are presented. Both compounds have planar sheets held together by intermolecular short contacts (hydrogen bonds and, for the latter, NO2···Br interactions); the sheets do not directly superimpose, so the effect of the π-stacking is not maximized. Solid-state fluorescence and extended-Hückel band-structure calculations are also presented for these materials.

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36

Yah, Weng On, Atsushi Irie, Nattha Jiravanichanun, Hideyuki Otsuka, and Atsushi Takahara. "Molecular Aggregation State and Electrical Properties of Terthiophenes/Imogolite Nanohybrids." Bulletin of the Chemical Society of Japan 84, no. 9 (September 15, 2011): 893–902. http://dx.doi.org/10.1246/bcsj.20110080.

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37

Díaz, Fernando R., Ignacio Jessop, Christian Núñez, M. Angélica del Valle, Pedro Pablo Zamora, and Jean Christian Bernède. "Electrochemical synthesis of poly(3′-alkyl-terthiophenes). Characterization and applications." Polymer Bulletin 68, no. 7 (October 16, 2011): 1801–13. http://dx.doi.org/10.1007/s00289-011-0648-z.

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38

Chen, Li, Jian Ping Gong, Yutaka Ohsedo, and Yoshihito Osada. "Study on Doping Behaviors of Vinyl Hydrogels with Pendant Terthiophenes." Macromolecular Chemistry and Physics 204, no. 17 (November 2003): 2142–46. http://dx.doi.org/10.1002/macp.200350067.

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39

Vélez, J. H., F. R. Díaz, M. A. del Valle, J. C. Bernéde, and J. P. Soto. "Synthesis of 3′,4′-disubstituted terthiophenes—Characterization and electropolymerization. II. 3′-bromo-4′-thienyl-2,2′:5′,2′-terthiophene and 3′,4′-diphenyl-2,2′:5′,2′-terthiophene in photovoltaic displays." Journal of Applied Polymer Science 109, no. 3 (2008): 1722–29. http://dx.doi.org/10.1002/app.28313.

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40

Sordello, Fabrizio, Claudio Minero, Guido Viscardi, and Pierluigi Quagliotto. "Highly Photoactive Polythiophenes Obtained by Electrochemical Synthesis from Bipyridine-Containing Terthiophenes." Energies 12, no. 3 (January 22, 2019): 341. http://dx.doi.org/10.3390/en12030341.

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According to numerous previous reports, a Z-scheme with two photon absorbers is the most promising strategy to achieve artificial photosynthesis, but in addition to two efficient catalysts — one for oxygen evolution, the other for CO2 reduction — two different and complementary semiconducting sensitizers are required. Here we present the synthesis of two bipyridine-functionalized terthiophenes, which can be electropolymerized to give photoactive p-type semiconductors the capability to perform as photocathode in photoelectrochemical cells for water photosplitting or artificial photosynthesis. Indeed the bipyridine moiety in their structure allows the binding of transition metal carbonyl complexes employed in CO2 reduction, and their band-gap is suitable for the coupling with wide band-gap semiconductors, which have already found application as photoanodes. Finally, they are characterized by photogenerated charge carrier density between 1.1 and 1.4 × 1019 cm−3, with first-order recombination constant of 0.7–1.8 × 10−2 s−1. These figures are of the same order of magnitude of their inorganic counterparts and would therefore guarantee photoconductivity of the device and the activation of the organometallic catalysts with which they should be coupled to function as photocathodes for CO2 reduction.

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41

Chen, J., C. O. Too, A. K. Burrell, G. E. Collis, D. L. Officer, and G. G. Wallace. "Photovoltaic devices based on poly(bis-terthiophenes) and substituted poly(bisterthiophene)." Synthetic Metals 137, no. 1-3 (April 2003): 1373–74. http://dx.doi.org/10.1016/s0379-6779(02)01120-7.

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42

DiCésare, Nicolas, Michel Belletête, Mario Leclerc, and Gilles Durocher. "Temperature-dependent spectroscopy and photophysics of substituted terthiophenes in fluid solution." Synthetic Metals 98, no. 1 (November 1998): 31–40. http://dx.doi.org/10.1016/s0379-6779(98)00142-8.

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43

Engelmann, Gūnnar, Reinhard Stößer, Gerhard Koßmehl, Werner Jugelt, and Hans-Peter Welzel. "EPR investigations of β-deuteriated 5,5″-dimethyl-2,2′:5′,2″-terthiophenes." J. Chem. Soc., Perkin Trans. 2, no. 9 (1996): 2015–19. http://dx.doi.org/10.1039/p29960002015.

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44

Clarke, Tracey M., Keith C. Gordon, David L. Officer, Simon B. Hall, Gavin E. Collis, and Anthony K. Burrell. "Theoretical and Spectroscopic Study of a Series of Styryl-Substituted Terthiophenes." Journal of Physical Chemistry A 107, no. 51 (December 2003): 11505–16. http://dx.doi.org/10.1021/jp030619y.

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45

Santos, M. J. L., A. F. Rubira, R. M. Pontes, E. A. Basso, and E. M. Girotto. "Electrochromic properties of poly(alkoxy-terthiophenes): an experimental and theoretical investigation." Journal of Solid State Electrochemistry 10, no. 2 (May 20, 2005): 117–22. http://dx.doi.org/10.1007/s10008-005-0679-1.

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46

Chahma, M’hamed, and Somaiah Almubayedh. "Synthesis and characterization of terthiophene bearing stable radicals." Canadian Journal of Chemistry 99, no. 1 (January 2021): 24–30. http://dx.doi.org/10.1139/cjc-2020-0338.

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The synthesis and characterization of a new terthiophene bearing stable radical II is described. Through a cross coupling reaction between 2-tributylstannylthiophene and 6-(2,5-dibromo-thiophene-3-yl)pyridine-2-carboxaldehyde (2), 6-[2,2′:5′,2″]terthiophen-3′-ylpyridine-2-carboxaldehyde (3) was prepared. The condensation of 3 with 2, 4-diisopropylcarbonohydrazide bis-hydrochloride affords the heterocyclic tetrazane (4), which was oxidized with 1,4-benzoquinone to form the stable radical II. II characterized by IR, ESR, and cyclic voltammetry. Oxidative electropolymerization of II and its precursor 4 at oxidation peak potential of the terthiophene using cyclic voltammetric scans produces radical functionalized polyterthiophene on a platinum electrode (poly(II)-Pt).

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47

NAKAYAMA, J., Y. TING, Y. SUGIHARA, and A. ISHII. "ChemInform Abstract: Synthesis of Highly Congested Bi- and Terthiophenes; 3,4,3′,4′-Tetra- tert-butylbithiophene and 3′,4′-Di-tert-butyl-2,2′:5′,2′′-terthiophene." ChemInform 28, no. 21 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199721120.

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48

Zhao, Qun, Jianwei Wang, Jason L. Freeman, Makeba Murphy-Jolly, Ashley M. Wright, Debra J. Scardino, Nathan I. Hammer, Christopher M. Lawson, and Gary M. Gray. "Syntheses, and Optical, Fluorescence, and Nonlinear Optical Characterization of Phosphine-Substituted Terthiophenes." Inorganic Chemistry 50, no. 5 (March 7, 2011): 2015–27. http://dx.doi.org/10.1021/ic101624y.

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49

Grant, Daina K., Kenneth W. Jolley, David L. Officer, Keith C. Gordon, and Tracey M. Clarke. "Towards functionalized poly(terthiophenes): regioselective synthesis of oligoether-substituted bis(styryl)sexithiophenes." Organic & Biomolecular Chemistry 3, no. 10 (2005): 2008. http://dx.doi.org/10.1039/b502791h.

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50

Chen, Li, Tatsuo Kaneko, Jian Ping Gong, Yoshihito Osada, Yutaka Ohsedo, and Yasuhiko Shirota. "Crystalline Structure and Thermal Behavior of Water-Soluble Copolymers with Pendant Terthiophenes." Macromolecular Chemistry and Physics 203, no. 1 (January 1, 2002): 176–81. http://dx.doi.org/10.1002/1521-3935(20020101)203:1<176::aid-macp176>3.0.co;2-4.

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