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Collect. Czech. Chem. Commun. 2002, 67, 645-664
https://doi.org/10.1135/cccc20020645

Reactivity of [1]Benzothieno[3,2-b][1]benzothiophene - Electrophilic and Metallation Reactions

Bedřich Košata, Václav Kozmík and Jiří Svoboda*

Department of Organic Chemistry, Institute of Chemical Technology, Prague, 166 28 Prague 6, Czech Republic

Crossref Cited-by Linking

  • S. K. Nandana, P. Rahul, Ann Babu Sheba, John Jubi, Hopf Henning: A Review on the Synthetic Methods towards Benzothienobenzothiophenes. The Chemical Record 2024, 24. <https://doi.org/10.1002/tcr.202400019>
  • Fortunato Anna, Hensel Rafael Cintra, Casalini Stefano, Mba Miriam: Self-Assembly and Electrical Conductivity of a New [1]benzothieno[3,2-b][1]-benzothiophene (BTBT)-Peptide Hydrogel. Molecules 2023, 28, 2917. <https://doi.org/10.3390/molecules28072917>
  • Kadoya Tomofumi, Mano Shotaro, Hori Aoi, Tahara Keishiro, Sugimoto Kunihisa, Kubo Kazuya, Abe Masaaki, Tajima Hiroyuki, Yamada Jun-ichi: Steric effect of halogen substitution in an unsymmetrical benzothienobenzothiophene organic semiconductor. Organic Electronics 2020, 78, 105570. <https://doi.org/10.1016/j.orgel.2019.105570>
  • Kitamura Tsugio, Morita Kazuhiro, Nakamori Haruka, Oyamada Juzo: Synthesis of [1]Benzothieno[3,2-b][1]benzothiophene Derivatives via Successive Iodocyclization/Photocyclization of Alkynes. J. Org. Chem. 2019, 84, 4191. <https://doi.org/10.1021/acs.joc.9b00213>
  • Higashino Toshiki, Ueda Akira, Mori Hatsumi: Di- and tetramethoxy benzothienobenzothiophenes: substitution position effects on the intermolecular interactions, crystal packing and transistor properties. New J. Chem. 2019, 43, 884. <https://doi.org/10.1039/C8NJ04251A>
  • He Yu, Guo Shenghui, He Yaowu, Murtaza Imran, Li Aiyuan, Zeng Xianzhe, Guo Yitong, Zhao Yang, Chen Xiaolong, Meng Hong: Investigating the Thermal Stability of Organic Thin‐Film Transistors and Phototransistors Based on [1]‐Benzothieno‐[3,2‐b]‐[1]‐benzothiophene Dimeric Derivatives. Chemistry A European J 2018, 24, 16595. <https://doi.org/10.1002/chem.201803542>
  • Guo Shenghui, He Yaowu, Murtaza Imran, Tan Jiahui, Pan Junyou, Guo Yitong, Zhu Yanan, He Yu, Meng Hong: Alkoxy substituted [1]benzothieno[3,2-b][1]benzothiophene derivative with improved performance in organic thin film transistors. Organic Electronics 2018, 56, 68. <https://doi.org/10.1016/j.orgel.2018.02.003>
  • Reddy M. Rajeshkumar, Kim Hyungsug, Kim Choongik, Seo SungYong: 2-Thiopene[1]benzothieno[3,2-b]benzothiophene derivatives as solution-processable organic semiconductors for organic thin-film transistors. Synthetic Metals 2018, 235, 153. <https://doi.org/10.1016/j.synthmet.2017.12.012>
  • Chung Hyunjoong, Dudenko Dmytro, Zhang Fengjiao, D’Avino Gabriele, Ruzié Christian, Richard Audrey, Schweicher Guillaume, Cornil Jérôme, Beljonne David, Geerts Yves, Diao Ying: Rotator side chains trigger cooperative transition for shape and function memory effect in organic semiconductors. Nat Commun 2018, 9. <https://doi.org/10.1038/s41467-017-02607-9>
  • Borshchev O. V., Sizov A. S., Agina E. V., Bessonov A. A., Ponomarenko S. A.: Synthesis of organosilicon derivatives of [1]benzothieno[3,2-b][1]-benzothiophene for efficient monolayer Langmuir–Blodgett organic field effect transistors. Chem. Commun. 2017, 53, 885. <https://doi.org/10.1039/C6CC08654C>
  • Yao Chao, Chen Xiaolong, He Yaowu, Guo Yitong, Murtaza Imran, Meng Hong: Design and characterization of methoxy modified organic semiconductors based on phenyl[1]benzothieno[3,2-b][1]benzothiophene. RSC Adv. 2017, 7, 5514. <https://doi.org/10.1039/C6RA28074A>
  • Higashino Toshiki, Ueda Akira, Yoshida Junya, Mori Hatsumi: Improved stability of a metallic state in benzothienobenzothiophene-based molecular conductors: an effective increase of dimensionality with hydrogen bonds. Chem. Commun. 2017, 53, 3426. <https://doi.org/10.1039/C7CC00784A>
  • He Yaowu, Xu Wenjun, Murtaza Imran, Zhang Dongwei, He Chao, Zhu Yanan, Meng Hong: Molecular phase engineering of organic semiconductors based on a [1]benzothieno[3,2-b][1]benzothiophene core. RSC Adv. 2016, 6, 95149. <https://doi.org/10.1039/C6RA22999A>
  • Ruzié Christian, Karpinska Jolanta, Laurent Anne, Sanguinet Lionel, Hunter Simon, Anthopoulos Thomas D., Lemaur Vincent, Cornil Jérôme, Kennedy Alan R., Fenwick Oliver, Samorì Paolo, Schweicher Guillaume, Chattopadhyay Basab, Geerts Yves Henri: Design, synthesis, chemical stability, packing, cyclic voltammetry, ionisation potential, and charge transport of [1]benzothieno[3,2-b][1]benzothiophene derivatives. J. Mater. Chem. C 2016, 4, 4863. <https://doi.org/10.1039/C6TC01409G>
  • Roche Gilles H., Tsai Yu-Tang, Clevers Simon, Thuau Damien, Castet Frédéric, Geerts Yves H., Moreau Joël J. E., Wantz Guillaume, Dautel Olivier J.: The role of H-bonds in the solid state organization of [1]benzothieno[3,2-b][1]benzothiophene (BTBT) structures: bis(hydroxy-hexyl)-BTBT, as a functional derivative offering efficient air stable organic field effect transistors (OFETs). J. Mater. Chem. C 2016, 4, 6742. <https://doi.org/10.1039/C6TC01814A>
  • Konishi Tsubasa, Yamaguchi Kazuo: Fabrication of Bifunctional Surfaces from a Patterned Self-assembled Monolayer of 2-Nitrobenzyl Carbamate-bearing Silane Coupling Agent. Chem. Lett. 2016, 45, 469. <https://doi.org/10.1246/cl.160052>
  • Niebel Claude, Kim Yeongin, Ruzié Christian, Karpinska Jolanta, Chattopadhyay Basab, Schweicher Guillaume, Richard Audrey, Lemaur Vincent, Olivier Yoann, Cornil Jérôme, Kennedy Alan R., Diao Ying, Lee Wen-Ya, Mannsfeld Stefan, Bao Zhenan, Geerts Yves H.: Thienoacene dimers based on the thieno[3,2-b]thiophene moiety: synthesis, characterization and electronic properties. J. Mater. Chem. C 2015, 3, 674. <https://doi.org/10.1039/C4TC02158D>
  • Colella Silvia, Ruzié Christian, Schweicher Guillaume, Arlin Jean‐Baptiste, Karpinska Jolanta, Geerts Yves, Samorì Paolo: High Mobility in Solution‐Processed 2,7‐Dialkyl‐[1]benzothieno[3,2‐b][1]benzothiophene‐Based Field‐Effect Transistors Prepared with a Simplified Deposition Method. ChemPlusChem 2014, 79, 371. <https://doi.org/10.1002/cplu.201300414>
  • Minami Sojiro, Hirano Koji, Satoh Tetsuya, Miura Masahiro: Synthesis of [1]benzothieno[3,2-b][1]benzothiophene (BTBT) and its higher homologs through palladium-catalyzed intramolecular decarboxylative arylation. Tetrahedron Letters 2014, 55, 4175. <https://doi.org/10.1016/j.tetlet.2014.05.084>
  • Yu Han, Li Weili, Tian Hongkun, Wang Haibo, Yan Donghang, Zhang Jingping, Geng Yanhou, Wang Fosong: Benzothienobenzothiophene-Based Conjugated Oligomers as Semiconductors for Stable Organic Thin-Film Transistors. ACS Appl. Mater. Interfaces 2014, 6, 5255. <https://doi.org/10.1021/am500598f>
  • Takimiya Kazuo, Osaka Itaru, Mori Takamichi, Nakano Masahiro: Organic Semiconductors Based on [1]Benzothieno[3,2-b][1]benzothiophene Substructure. Acc. Chem. Res. 2014, 47, 1493. <https://doi.org/10.1021/ar400282g>
  • Grigoriadis Christos, Niebel Claude, Ruzié Christian, Geerts Yves H., Floudas George: Order, Viscoelastic, and Dielectric Properties of Symmetric and Asymmetric Alkyl[1]benzothieno[3,2-b][1]benzothiophenes. J. Phys. Chem. B 2014, 118, 1443. <https://doi.org/10.1021/jp412422e>
  • Vyas Vijay S., Gutzler Rico, Nuss Jürgen, Kern Klaus, Lotsch Bettina V.: Optical gap in herringbone and π-stacked crystals of [1]benzothieno[3,2-b]benzothiophene and its brominated derivative. CrystEngComm 2014, 16, 7389. <https://doi.org/10.1039/C4CE00752B>
  • Takimiya Kazuo, Nakano Masahiro, Kang Myeong Jin, Miyazaki Eigo, Osaka Itaru: Thienannulation: Efficient Synthesis of π‐Extended Thienoacenes Applicable to Organic Semiconductors. Eur J Org Chem 2013, 2013, 217. <https://doi.org/10.1002/ejoc.201201139>
  • Mori Takamichi, Nishimura Takeshi, Yamamoto Tatsuya, Doi Iori, Miyazaki Eigo, Osaka Itaru, Takimiya Kazuo: Consecutive Thiophene-Annulation Approach to π-Extended Thienoacene-Based Organic Semiconductors with [1]Benzothieno[3,2-b][1]benzothiophene (BTBT) Substructure. J. Am. Chem. Soc. 2013, 135, 13900. <https://doi.org/10.1021/ja406257u>
  • Ruzié Christian, Karpinska Jolanta, Kennedy Alan R., Geerts Yves H.: Synthesis of 1,6-, 2,7-, 3,8-, and 4,9-Isomers of Didodecyl[1]benzothieno[3,2-b][1]benzothiophenes. J. Org. Chem. 2013, 78, 7741. <https://doi.org/10.1021/jo401134c>
  • Amin Atefeh Y., Khassanov Artoem, Reuter Knud, Meyer-Friedrichsen Timo, Halik Marcus: Low-Voltage Organic Field Effect Transistors with a 2-Tridecyl[1]benzothieno[3,2-b][1]benzothiophene Semiconductor Layer. J. Am. Chem. Soc. 2012, 134, 16548. <https://doi.org/10.1021/ja307802q>
  • Takimiya Kazuo, Shinamura Shoji, Osaka Itaru, Miyazaki Eigo: Thienoacene‐Based Organic Semiconductors. Advanced Materials 2011, 23, 4347. <https://doi.org/10.1002/adma.201102007>
  • Chernichenko Konstantin, Emelyanov Nikolai, Gridnev Ilya, Nenajdenko Valentine G.: Unusual thiophilic ring-opening of fused oligothiophenes with organolithium reagents. Tetrahed 2011, 67, 6812. <https://doi.org/10.1016/j.tet.2011.06.082>
  • Saito Masahiko, Osaka Itaru, Miyazaki Eigo, Takimiya Kazuo, Kuwabara Hirokazu, Ikeda Masaaki: One-step synthesis of [1]benzothieno[3,2-b][1]benzothiophene from o-chlorobenzaldehyde. Tetrahedron Letters 2011, 52, 285. <https://doi.org/10.1016/j.tetlet.2010.11.021>
  • Amin Atefeh Y., Reuter Knud, Meyer-Friedrichsen Timo, Halik Marcus: Interface Engineering in High-Performance Low-Voltage Organic Thin-Film Transistors Based on 2,7-Dialkyl-[1]benzothieno[3,2-b][1]benzothiophenes. Langmuir 2011, 27, 15340. <https://doi.org/10.1021/la203041x>
  • Saito Masahiko, Yamamoto Tatsuya, Osaka Itaru, Miyazaki Eigo, Takimiya Kazuo, Kuwabara Hirokazu, Ikeda Masaaki: Facile synthesis of [1]benzothieno[3,2-b]benzothiophene from o-dihalostilbenes. Tetrahedron Letters 2010, 51, 5277. <https://doi.org/10.1016/j.tetlet.2010.07.152>
  • Machara Aleš, Kozmík Václav, Pojarová Michaela, Dvořáková Hana, Svoboda Jiří: Preparation and rearrangement study of novel thiophenium- and selenophenium-ylides. Collect. Czech. Chem. Commun. 2009, 74, 785. <https://doi.org/10.1135/cccc2009001>
  • Machara Aleš, Pojarová Michaela, Svoboda Jiří: Synthesis and Cycloaddition Reaction of 3-Vinylthieno[3,2-b][1]benzothiophene. Collect. Czech. Chem. Commun. 2007, 72, 952. <https://doi.org/10.1135/cccc20070952>
  • Lô Ch., Adenier A., Chane-Ching K.I., Maurel F., Aaron J.J., Kosata B., Svoboda J.: A novel fluorescent, conducting polymer: Poly[1-(thiophene-2-yl)benzothieno[3,2-b]benzothiophene] electrosynthesis, characterization and optical properties. Synthetic Metals 2006, 156, 256. <https://doi.org/10.1016/j.synthmet.2005.12.003>
  • Košata Bedřich, Svoboda Jiří, Novotná Vladimíra, Glogarová Milada: Synthesis and mesomorphic properties of liquid crystalline [1]benzothieno[3,2-b][1]benzothiophene derivatives. Liq Crist 2004, 31, 1367. <https://doi.org/10.1080/02678290412331282091>
  • Kosˇata Bedrˇich, Kozmik Václav, Svoboda Jirˇí, Novotná Vladimíra, Vaneˇk Prˇemysl, Glogarová Milada: Novel liquid crystals based on [1]benzothieno[3,2- b][1]benzothiophene. Liq Crist 2003, 30, 603. <https://doi.org/10.1080/0267829031000097484>
  • Kosata Bedrich, Kozmik Vaclav, Svoboda Jiri: Reactivity of [1]Benzothieno[3,2‐b][1]benzothiophene — Electrophilic and Metalation Reactions. ChemInform 2002, 33, 121. <https://doi.org/10.1002/chin.200240121>