ACS Publications. Most Trusted. Most Cited. Most Read
2,7-Diphenyl[1]benzothieno[3,2-b]benzothiophene, A New Organic Semiconductor for Air-Stable Organic Field-Effect Transistors with Mobilities up to 2.0 cm2 V-1 s-1
My Activity

Figure 1Loading Img
    Communication

    2,7-Diphenyl[1]benzothieno[3,2-b]benzothiophene, A New Organic Semiconductor for Air-Stable Organic Field-Effect Transistors with Mobilities up to 2.0 cm2 V-1 s-1
    Click to copy article linkArticle link copied!

    View Author Information
    Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan, Institute for Advanced Materials Research, Hiroshima University, Higashi-Hiroshima 739-8530, Japan, and Department of Applied Chemistry, Faculty of Engineering, Tokai University, 1117 Kitakaname, Hiratsuka 259-1292, Japan
    Other Access OptionsSupporting Information (1)

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2006, 128, 39, 12604–12605
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ja064052l
    Published September 8, 2006
    Copyright © 2006 American Chemical Society

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    Vapor-deposited thin films of a newly developed sulfur-containing heteroarene, 2,7-diphenyl[1]benzothieno[3,2-b][1]benzothiophene (DPh-BTBT), were used as an active layer of OFETs, which showed excellent FET characteristics in ambient conditions with mobilities of ∼2.0 cm2 V-1 s-1 and Ion/Ioff of 107.

    Copyright © 2006 American Chemical Society

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    *

    In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

     Graduate School of Engineering, Hiroshima University.

     Institute for Advanced Materials Research, Hiroshima University.

    §

     Tokai University.

    Supporting Information Available

    Click to copy section linkSection link copied!

    Experimental details for the synthesis and characterization of DPh-BTBT, device fabrication, XRDs, DFT calculations, AFM images of DPh-BTBT thin films, and FET characteristics of DPh-BSBS-based OFETs fabricated on silanized substrates. This material is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!

    This article is cited by 399 publications.

    1. Keishiro Tahara, Akihito Kobayashi, Mamoru Fujitsuka, Yasuko Osakada, Ken Tokunaga, Takashi Ikeda, Masaaki Abe. Cyclometalated Pt(II) Complex Appending a Pyridyl Ligand with a Benzothienobenzothiophene (BTBT) Unit: Synthesis, Photophysical Properties, and an Unusual Shift of Centered Ligands in Excited States. Organometallics 2024, 43 (8) , 840-848. https://doi.org/10.1021/acs.organomet.4c00019
    2. Kohei Sambe, Takashi Takeda, Norihisa Hoshino, Wakana Matsuda, Kazuki Shimada, Kanae Tsujita, Shingo Maruyama, Shunsuke Yamamoto, Shu Seki, Yuji Matsumoto, Tomoyuki Akutagawa. Carrier Transport Switching of Ferroelectric BTBT Derivative. Journal of the American Chemical Society 2024, 146 (12) , 8557-8566. https://doi.org/10.1021/jacs.4c00514
    3. Kohei Sambe, Takashi Takeda, Norihisa Hoshino, Wakana Matsuda, Riku Miura, Kanae Tsujita, Shingo Maruyama, Shunsuke Yamamoto, Shu Seki, Yuji Matsumoto, Tomoyuki Akutagawa. Ferroelectric Organic Semiconductor: [1]Benzothieno[3,2-b][1]benzothiophene-Bearing Hydrogen-Bonding −CONHC14H29 Chain. ACS Applied Materials & Interfaces 2023, 15 (50) , 58711-58722. https://doi.org/10.1021/acsami.3c14476
    4. Han Yan, Fen-Dou Wang, Min Wang, Liang Ye, Pinhua Li. Photoinduced Radical Cyclization of 2-Alkynylthioanisoles with Disulfides without an External Photocatalyst. The Journal of Organic Chemistry 2023, 88 (21) , 15288-15297. https://doi.org/10.1021/acs.joc.3c01776
    5. Nimrod Benshalom, Maor Asher, Rémy Jouclas, Roman Korobko, Guillaume Schweicher, Jie Liu, Yves Geerts, Olle Hellman, Omer Yaffe. Phonon–Phonon Interactions in the Polarization Dependence of Raman Scattering. The Journal of Physical Chemistry C 2023, 127 (36) , 18099-18106. https://doi.org/10.1021/acs.jpcc.3c03850
    6. Sheba Ann Babu, Varsha P. V, Susanna Poulose, Sunil Varughese, Jubi John. Copper-Catalyzed Annulation of Electrophilic Benzannulated Heterocycles with 2-Aminopyridine and 2-Aminoquinoline: Direct Access toward Polyring-Fused Imidazo[1,2-a]pyridines. The Journal of Organic Chemistry 2023, 88 (14) , 10027-10039. https://doi.org/10.1021/acs.joc.3c00849
    7. Zhongwei Liu, Ting Jiang, Yanru Li, Yunpeng Lou, Chan Zhang, Jie Li, Yajing Sun, Xing Chen, Liqiang Li, Hongkun Tian, Deyang Ji, Zhuping Fei. Modulating the Alkylation Position on Terminal Thiophene Ring of Naphtho[2,3-b:6,7-b′] Bithieno[2,3-d] Thiophene (NBTT) for High-Performance Organic Optoelectronic Devices. ACS Applied Materials & Interfaces 2023, 15 (13) , 16930-16941. https://doi.org/10.1021/acsami.3c02547
    8. Tatsuhito Ando, Naoto Shimizu, Norihisa Yamamoto, Nobuyuki N. Matsuzawa, Hiroyuki Maeshima, Hiromasa Kaneko. Design of Molecules with Low Hole and Electron Reorganization Energy Using DFT Calculations and Bayesian Optimization. The Journal of Physical Chemistry A 2022, 126 (36) , 6336-6347. https://doi.org/10.1021/acs.jpca.2c05229
    9. Jibin Sivanarayanan, Ebin Sebastian, Kavya Vinod, Frank Würthner, Mahesh Hariharan. Ultrafast Intersystem Crossing in Selenium-Annulated Perylene Bisimide. The Journal of Physical Chemistry C 2022, 126 (31) , 13319-13326. https://doi.org/10.1021/acs.jpcc.2c03847
    10. Sebastian Stecko, Daniel T. Gryko. Multifunctional Heteropentalenes: From Synthesis to Optoelectronic Applications. JACS Au 2022, 2 (6) , 1290-1305. https://doi.org/10.1021/jacsau.2c00147
    11. Akhil Krishnan R., Sheba Ann Babu, Nitha P. Ravi, Sreeja Thulasi, Jubi John. Base-Mediated Annulation of Electrophilic Benzothiophene with Naphthols and Phenols: Accessing Benzothiophene-Fused Heteroacenes. The Journal of Organic Chemistry 2022, 87 (12) , 8017-8027. https://doi.org/10.1021/acs.joc.2c00645
    12. Alexey A. Volkov, Dmitry I. Bugaenko, Alexey V. Bogdanov, Alexander V. Karchava. Visible-Light-Driven Thioesterification of Aryl Halides with Potassium Thiocarboxylates: Transition-Metal Catalyst-Free Incorporation of Sulfur Functionalities into an Aromatic Ring. The Journal of Organic Chemistry 2022, 87 (12) , 8170-8182. https://doi.org/10.1021/acs.joc.2c00913
    13. Christina J. Kousseff, Roman Halaksa, Zachary S. Parr, Christian B. Nielsen. Mixed Ionic and Electronic Conduction in Small-Molecule Semiconductors. Chemical Reviews 2022, 122 (4) , 4397-4419. https://doi.org/10.1021/acs.chemrev.1c00314
    14. Kohei Fuchibe, Ibuki Mukohara, Atsushi Yamada, Daisuke Miyazaki, Ryo Takayama, Junji Ichikawa. Construction of Thienothiophene and Thienofuran Ring Systems via Ring Expansion of Difluorothiiranes Generated from Dithioesters. Organic Letters 2022, 24 (1) , 169-174. https://doi.org/10.1021/acs.orglett.1c03805
    15. Toshiki Higashino, Satoru Inoue, Shunto Arai, Hiroyuki Matsui, Naoya Toda, Sachio Horiuchi, Reiko Azumi, Tatsuo Hasegawa. Architecting Layered Crystalline Organic Semiconductors Based on Unsymmetric π-Extended Thienoacenes. Chemistry of Materials 2021, 33 (18) , 7379-7385. https://doi.org/10.1021/acs.chemmater.1c01972
    16. Gabriel Marques, Karl Leswing, Tim Robertson, David Giesen, Mathew D. Halls, Alexander Goldberg, Kyle Marshall, Joshua Staker, Tsuguo Morisato, Hiroyuki Maeshima, Hideyuki Arai, Masaru Sasago, Eiji Fujii, Nobuyuki N. Matsuzawa. De Novo Design of Molecules with Low Hole Reorganization Energy Based on a Quarter-Million Molecule DFT Screen. The Journal of Physical Chemistry A 2021, 125 (33) , 7331-7343. https://doi.org/10.1021/acs.jpca.1c04587
    17. Jiangfeng Wang, Yaowu He, Shenghui Guo, Muhammad Umair Ali, Changbin Zhao, Yanan Zhu, Tao Wang, Yunrui Wang, Jingsheng Miao, Guodan Wei, Hong Meng. Multifunctional Benzo[4,5]thieno[3,2-b]benzofuran Derivative with High Mobility and Luminescent Properties. ACS Applied Materials & Interfaces 2021, 13 (10) , 12250-12258. https://doi.org/10.1021/acsami.0c21286
    18. Akhil Krishnan R., Sheba Ann Babu, Nitha P. R., Jagadeesh Krishnan, Jubi John. Synthesis of Benzothienobenzofurans via Annulation of Electrophilic Benzothiophenes with Phenols. Organic Letters 2021, 23 (5) , 1814-1819. https://doi.org/10.1021/acs.orglett.1c00219
    19. Adara Babuji, Francesco Silvestri, Linus Pithan, Audrey Richard, Yves H. Geerts, Nir Tessler, Olga Solomeshch, Carmen Ocal, Esther Barrena. Effect of the Organic Semiconductor Side Groups on the Structural and Electronic Properties of Their Interface with Dopants. ACS Applied Materials & Interfaces 2020, 12 (51) , 57578-57586. https://doi.org/10.1021/acsami.0c17273
    20. Keishiro Tahara, Yuya Ashihara, Takashi Ikeda, Tomofumi Kadoya, Jun-ichi Fujisawa, Yoshiki Ozawa, Hiroyuki Tajima, Noriaki Toyoda, Yuichi Haruyama, Masaaki Abe. Immobilizing a π-Conjugated Catecholato Framework on Surfaces of SiO2 Insulator Films via a One-Atom Anchor of a Platinum Metal Center to Modulate Organic Transistor Performance. Inorganic Chemistry 2020, 59 (24) , 17945-17957. https://doi.org/10.1021/acs.inorgchem.0c02163
    21. Erin Antono, Nobuyuki N. Matsuzawa, Julia Ling, James Edward Saal, Hideyuki Arai, Masaru Sasago, Eiji Fujii. Machine-Learning Guided Quantum Chemical and Molecular Dynamics Calculations to Design Novel Hole-Conducting Organic Materials. The Journal of Physical Chemistry A 2020, 124 (40) , 8330-8340. https://doi.org/10.1021/acs.jpca.0c05769
    22. Takashi Ikeda, Keishiro Tahara, Tomofumi Kadoya, Hiroyuki Tajima, Noriaki Toyoda, Satoshi Yasuno, Yoshiki Ozawa, Masaaki Abe. Ferrocene on Insulator: Silane Coupling to a SiO2 Surface and Influence on Electrical Transport at a Buried Interface with an Organic Semiconductor Layer. Langmuir 2020, 36 (21) , 5809-5819. https://doi.org/10.1021/acs.langmuir.0c00515
    23. Nobuyuki N. Matsuzawa, Hideyuki Arai, Masaru Sasago, Eiji Fujii, Alexander Goldberg, Thomas J. Mustard, H. Shaun Kwak, David J. Giesen, Fabio Ranalli, Mathew D. Halls. Massive Theoretical Screen of Hole Conducting Organic Materials in the Heteroacene Family by Using a Cloud-Computing Environment. The Journal of Physical Chemistry A 2020, 124 (10) , 1981-1992. https://doi.org/10.1021/acs.jpca.9b10998
    24. Hu Chen, Andrew Wadsworth, Chun Ma, Alice Nanni, Weimin Zhang, Mark Nikolka, Alexander M. T. Luci, Luís M. A. Perdigão, Karl J. Thorley, Camila Cendra, Bryon Larson, Garry Rumbles, Thomas D. Anthopoulos, Alberto Salleo, Giovanni Costantini, Henning Sirringhaus, Iain McCulloch. The Effect of Ring Expansion in Thienobenzo[b]indacenodithiophene Polymers for Organic Field-Effect Transistors. Journal of the American Chemical Society 2019, 141 (47) , 18806-18813. https://doi.org/10.1021/jacs.9b09367
    25. Rachana Acharya, Boyu Peng, Paddy K. L. Chan, Guido Schmitz, Hagen Klauk. Achieving Ultralow Turn-On Voltages in Organic Thin-Film Transistors: Investigating Fluoroalkylphosphonic Acid Self-Assembled Monolayer Hybrid Dielectrics. ACS Applied Materials & Interfaces 2019, 11 (30) , 27104-27111. https://doi.org/10.1021/acsami.9b04361
    26. Hakan Usta, Dojeon Kim, Resul Ozdemir, Yunus Zorlu, Sanghyo Kim, M. Carmen Ruiz Delgado, Alexandra Harbuzaru, Seonhyoung Kim, Gökhan Demirel, Jongin Hong, Young-Geun Ha, Kilwon Cho, Antonio Facchetti, Myung-Gil Kim. High Electron Mobility in [1]Benzothieno[3,2-b][1]benzothiophene-Based Field-Effect Transistors: Toward n-Type BTBTs. Chemistry of Materials 2019, 31 (14) , 5254-5263. https://doi.org/10.1021/acs.chemmater.9b01614
    27. Ayumi Kawasaki, Takashi Takeda, Norihisa Hoshino, Wakana Matsuda, Shu Seki, Tomoyuki Akutagawa. High Thermally Stable n-Type Semiconductor up to 850 K Based on Dianionic Naphthalenediimide Derivative. The Journal of Physical Chemistry C 2019, 123 (25) , 15451-15457. https://doi.org/10.1021/acs.jpcc.9b03023
    28. Patrick Federmann, Hannah K. Wagner, Patrick W. Antoni, Jean-Marc Mörsdorf, José Luis Pérez Lustres, Hubert Wadepohl, Marcus Motzkus, Joachim Ballmann. P-Protected Diphosphadibenzo[a,e]pentalenes and Their Mono- and Dicationic P-Bridged Ladder Stilbenes. Organic Letters 2019, 21 (7) , 2033-2038. https://doi.org/10.1021/acs.orglett.9b00161
    29. Tomofumi Kadoya, Ryouji Oki, Yasuhiro Kiyota, Yuta Koyama, Toshiki Higashino, Kazuya Kubo, Takehiko Mori, Jun-ichi Yamada. Transport Properties of Molecular Conductors (BSBS)2XF6 (X = As, Sb, and Ta): Investigation of Intermolecular Transfer Integrals in the Radical-Cationic State of Benzothienobenzothiophene-Type Semiconductors. The Journal of Physical Chemistry C 2019, 123 (9) , 5216-5221. https://doi.org/10.1021/acs.jpcc.8b10687
    30. Hung-Yang Chen, Guillaume Schweicher, Miquel Planells, Sean M. Ryno, Katharina Broch, Andrew J. P. White, Dimitrios Simatos, Mark Little, Cameron Jellett, Samuel J. Cryer, Adam Marks, Michael Hurhangee, Jean-Luc Brédas, Henning Sirringhaus, Iain McCulloch. Crystal Engineering of Dibenzothiophenothieno[3,2-b]thiophene (DBTTT) Isomers for Organic Field-Effect Transistors. Chemistry of Materials 2018, 30 (21) , 7587-7592. https://doi.org/10.1021/acs.chemmater.8b02757
    31. Hongzhuo Wu, Yang Wang, Xiaolan Qiao, Deliang Wang, Xiaodi Yang, Hongxiang Li. Pyrrolo[3,2-b]pyrrole-Based Quinoidal Compounds For High Performance n-Channel Organic Field-Effect Transistor. Chemistry of Materials 2018, 30 (20) , 6992-6997. https://doi.org/10.1021/acs.chemmater.8b01791
    32. Xiaoyuan Zhao, Qiao Li, Jun Xu, Donghua Wang, Daisy Zhang-Negrerie, Yunfei Du. Cascade Synthesis of Benzothieno[3,2-b]indoles under Oxidative Conditions Mediated by CuBr and tert-Butyl Hydroperoxide. Organic Letters 2018, 20 (18) , 5933-5937. https://doi.org/10.1021/acs.orglett.8b02614
    33. Kodai Iijima, Ryo Sanada, Dongho Yoo, Ryonosuke Sato, Tadashi Kawamoto, Takehiko Mori. Carrier Charge Polarity in Mixed-Stack Charge-Transfer Crystals Containing Dithienobenzodithiophene. ACS Applied Materials & Interfaces 2018, 10 (12) , 10262-10269. https://doi.org/10.1021/acsami.8b00416
    34. Attrimuni P. Dhondge, Jian-You Chen, Ta Lin, Feng-Ming Yen, Kan-Wei Li, Hsin-Chun Hsieh, and Ming-Yu Kuo . Di-2-(2-oxindolin-3-ylidene)malononitrile Derivatives for N-Type Air-Stable Organic Field-Effect Transistors. Organic Letters 2018, 20 (1) , 40-43. https://doi.org/10.1021/acs.orglett.7b03284
    35. Vishnu Sukumaran Nair, Jibin Sun, Penglin Qi, Sifen Yang, Zitong Liu, Deqing Zhang, and Ayyappanpillai Ajayaghosh . Conjugated Random Donor–Acceptor Copolymers of [1]Benzothieno[3,2-b]benzothiophene and Diketopyrrolopyrrole Units for High Performance Polymeric Semiconductor Applications. Macromolecules 2016, 49 (17) , 6334-6342. https://doi.org/10.1021/acs.macromol.6b00954
    36. Mariusz Tasior and Daniel T. Gryko . Synthesis and Properties of Ladder-Type BN-Heteroacenes and Diazabenzoindoles Built on a Pyrrolopyrrole Scaffold. The Journal of Organic Chemistry 2016, 81 (15) , 6580-6586. https://doi.org/10.1021/acs.joc.6b01209
    37. Atsushi Yamamoto, Yasunori Matsui, Toshio Asada, Motoki Kumeda, Kenichiro Takagi, Yu Suenaga, Kunihiko Nagae, Eisuke Ohta, Hiroyasu Sato, Shiro Koseki, Hiroyoshi Naito, and Hiroshi Ikeda . Amorphous Solid Simulation and Trial Fabrication of the Organic Field-Effect Transistor of Tetrathienonaphthalenes Prepared by Using Microflow Photochemical Reactions: A Theoretical Calculation-Inspired Investigation. The Journal of Organic Chemistry 2016, 81 (8) , 3168-3176. https://doi.org/10.1021/acs.joc.6b00117
    38. Agostina L. Capodilupo, Eduardo Fabiano, Luisa De Marco, Giuseppe Ciccarella, Giuseppe Gigli, Carmela Martinelli, and Antonio Cardone . [1]Benzothieno[3,2-b]benzothiophene-Based Organic Dyes for Dye-Sensitized Solar Cells. The Journal of Organic Chemistry 2016, 81 (8) , 3235-3245. https://doi.org/10.1021/acs.joc.6b00192
    39. Yasuhiro Kiyota, Tomofumi Kadoya, Kaoru Yamamoto, Kodai Iijima, Toshiki Higashino, Tadashi Kawamoto, Kazuo Takimiya, and Takehiko Mori . Benzothienobenzothiophene-Based Molecular Conductors: High Conductivity, Large Thermoelectric Power Factor, and One-Dimensional Instability. Journal of the American Chemical Society 2016, 138 (11) , 3920-3925. https://doi.org/10.1021/jacs.6b01213
    40. Christopher Sutton, Chad Risko, and Jean-Luc Brédas . Noncovalent Intermolecular Interactions in Organic Electronic Materials: Implications for the Molecular Packing vs Electronic Properties of Acenes. Chemistry of Materials 2016, 28 (1) , 3-16. https://doi.org/10.1021/acs.chemmater.5b03266
    41. Minh Anh Truong and Koji Nakano . Synthesis of Benzofuro- and Indolo[3,2-b]indoles via Palladium-Catalyzed Double N-Arylation and Their Physical Properties. The Journal of Organic Chemistry 2015, 80 (22) , 11566-11572. https://doi.org/10.1021/acs.joc.5b02086
    42. Motonori Watanabe, Yasutaka Doi, Hidehisa Hagiwara, Aleksandar Tsekov Staykov, Shintaro Ida, Taisuke Matsumoto, Teruo Shinmyozu, and Tatsumi Ishihara . Synthesis and Investigation of the Effect of Substitution on the Structure, Physical Properties, and Electrochemical Properties of Anthracenodifuran Derivatives. The Journal of Organic Chemistry 2015, 80 (18) , 9159-9166. https://doi.org/10.1021/acs.joc.5b01525
    43. Masahiro Abe, Takamichi Mori, Itaru Osaka, Kunihisa Sugimoto, and Kazuo Takimiya . Thermally, Operationally, and Environmentally Stable Organic Thin-Film Transistors Based on Bis[1]benzothieno[2,3-d:2′,3′-d′]naphtho[2,3-b:6,7-b′]dithiophene Derivatives: Effective Synthesis, Electronic Structures, and Structure–Property Relationship. Chemistry of Materials 2015, 27 (14) , 5049-5057. https://doi.org/10.1021/acs.chemmater.5b01608
    44. Mehmet Emin Cinar and Turan Ozturk . Thienothiophenes, Dithienothiophenes, and Thienoacenes: Syntheses, Oligomers, Polymers, and Properties. Chemical Reviews 2015, 115 (9) , 3036-3140. https://doi.org/10.1021/cr500271a
    45. Takashi Takeda and Tomoyuki Akutagawa . Preparation, Structure, and Redox Behavior of Bis(diarylmethylene)dihydrothiophene and Its π-Extended Analogues. The Journal of Organic Chemistry 2015, 80 (4) , 2455-2461. https://doi.org/10.1021/acs.joc.5b00021
    46. Hiroyuki Tanaka, Katsuyuki Shizu, Jiyoung Lee, and Chihaya Adachi . Effect of Atom Substitution in Chalcogenodiazole-Containing Thermally Activated Delayed Fluorescence Emitters on Radiationless Transition. The Journal of Physical Chemistry C 2015, 119 (6) , 2948-2955. https://doi.org/10.1021/jp510751n
    47. Jin-Dou Huang, Shuo Chai, Huipeng Ma, and Bin Dong . Impact of Edge-Core Structures and Substituent Effects on the Electronic and Charge-Transport Properties of Heteroaromatic Ring-Fused Oligomers. The Journal of Physical Chemistry C 2015, 119 (1) , 33-44. https://doi.org/10.1021/jp5086922
    48. Kazuo Takimiya, Itaru Osaka, Takamichi Mori, and Masahiro Nakano . Organic Semiconductors Based on [1]Benzothieno[3,2-b][1]benzothiophene Substructure. Accounts of Chemical Research 2014, 47 (5) , 1493-1502. https://doi.org/10.1021/ar400282g
    49. Han Yu, Weili Li, Hongkun Tian, Haibo Wang, Donghang Yan, Jingping Zhang, Yanhou Geng, and Fosong Wang . Benzothienobenzothiophene-Based Conjugated Oligomers as Semiconductors for Stable Organic Thin-Film Transistors. ACS Applied Materials & Interfaces 2014, 6 (7) , 5255-5262. https://doi.org/10.1021/am500598f
    50. Sabin-Lucian Suraru, Christian Burschka, and Frank Würthner . Diindole-Annulated Naphthalene Diimides: Synthesis and Optical and Electronic Properties of Syn- and Anti-Isomers. The Journal of Organic Chemistry 2014, 79 (1) , 128-139. https://doi.org/10.1021/jo402365s
    51. Qi Xiao, Tsuneaki Sakurai, Takahiro Fukino, Kouki Akaike, Yoshihito Honsho, Akinori Saeki, Shu Seki, Kenichi Kato, Masaki Takata, and Takuzo Aida . Propeller-Shaped Fused Oligothiophenes: A Remarkable Effect of the Topology of Sulfur Atoms on Columnar Stacking. Journal of the American Chemical Society 2013, 135 (49) , 18268-18271. https://doi.org/10.1021/ja4092769
    52. Takamichi Mori, Takeshi Nishimura, Tatsuya Yamamoto, Iori Doi, Eigo Miyazaki, Itaru Osaka, and Kazuo Takimiya . Consecutive Thiophene-Annulation Approach to π-Extended Thienoacene-Based Organic Semiconductors with [1]Benzothieno[3,2-b][1]benzothiophene (BTBT) Substructure. Journal of the American Chemical Society 2013, 135 (37) , 13900-13913. https://doi.org/10.1021/ja406257u
    53. Jian Zhao, Kazuaki Oniwa, Naoki Asao, Yoshinori Yamamoto, and Tienan Jin . Pd-Catalyzed Cascade Crossover Annulation of o-Alkynylarylhalides and Diarylacetylenes Leading to Dibenzo[a,e]pentalenes. Journal of the American Chemical Society 2013, 135 (28) , 10222-10225. https://doi.org/10.1021/ja403382d
    54. Manabu Ohtomo, Yuya Tsuchida, Naoki Muraya, Takashi Yanase, Seiji Sakai, Tetsu Yonezawa, Taro Nagahama, Tetsuya Hasegawa, and Toshihiro Shimada . In-Plane Orientation Control of 2,7-Diphenyl[1]benzothieno[3,2-b][1]benzothiophene Monolayer on Bismuth-Terminated Si(111) Vicinal Surfaces with Wettability Optimization. The Journal of Physical Chemistry C 2013, 117 (22) , 11555-11561. https://doi.org/10.1021/jp3117837
    55. Myeong Jin Kang, Eigo Miyazaki, Itaru Osaka, Kazuo Takimiya, and Akiko Nakao . Diphenyl Derivatives of Dinaphtho[2,3-b:2′,3′-f]thieno[3,2-b]thiophene: Organic Semiconductors for Thermally Stable Thin-Film Transistors. ACS Applied Materials & Interfaces 2013, 5 (7) , 2331-2336. https://doi.org/10.1021/am3026163
    56. Xiaoming He, Javier Borau-Garcia, Alva Y. Y. Woo, Simon Trudel, and Thomas Baumgartner . Dithieno[3,2-c:2′,3′-e]-2,7-diketophosphepin: A Unique Building Block for Multifunctional π-Conjugated Materials. Journal of the American Chemical Society 2013, 135 (3) , 1137-1147. https://doi.org/10.1021/ja310680x
    57. Peng-Yi Huang, Liang-Hsiang Chen, Choongik Kim, Hsiu-Chieh Chang, You-jhih Liang, Chieh-Yuan Feng, Chia-Ming Yeh, Jia-Chong Ho, Cheng-Chung Lee, and Ming-Chou Chen . High-Performance Bottom-Contact Organic Thin-Film Transistors Based on Benzo[d,d′]thieno[3,2-b;4,5-b′]dithiophenes (BTDTs) Derivatives. ACS Applied Materials & Interfaces 2012, 4 (12) , 6992-6998. https://doi.org/10.1021/am3022448
    58. Long Chen, Sreenivasa R. Puniredd, Yuan-Zhi Tan, Martin Baumgarten, Ute Zschieschang, Volker Enkelmann, Wojciech Pisula, Xinliang Feng, Hagen Klauk, and Klaus Müllen . Hexathienocoronenes: Synthesis and Self-Organization. Journal of the American Chemical Society 2012, 134 (43) , 17869-17872. https://doi.org/10.1021/ja3082395
    59. Tatsuya Yamamoto, Takeshi Nishimura, Takamichi Mori, Eigo Miyazaki, Itaru Osaka, and Kazuo Takimiya . Largely π-Extended Thienoacenes with Internal Thieno[3,2-b]thiophene Substructures: Synthesis, Characterization, and Organic Field-Effect Transistor Applications. Organic Letters 2012, 14 (18) , 4914-4917. https://doi.org/10.1021/ol302243t
    60. Weifeng Zhang, Xiangnan Sun, Pingfang Xia, Jianyao Huang, Gui Yu, Man Shing Wong, Yunqi Liu, and Daoben Zhu . Novel Butterfly-Shaped Fused Heteroacenes: Synthesis, Properties, and Device Performance of Solution-Processed Field-Effect Transistors. Organic Letters 2012, 14 (17) , 4382-4385. https://doi.org/10.1021/ol301852m
    61. Masashi Mamada, Tsukuru Minamiki, Hiroshi Katagiri, and Shizuo Tokito . Synthesis, Physical Properties, and Field-Effect Mobility of Isomerically Pure syn-/anti-Anthradithiophene Derivatives. Organic Letters 2012, 14 (16) , 4062-4065. https://doi.org/10.1021/ol301626u
    62. Jianyao Huang, Hao Luo, Liping Wang, Yunlong Guo, Weifeng Zhang, Huajie Chen, Minliang Zhu, Yunqi Liu, and Gui Yu . Dibenzoannelated Tetrathienoacene: Synthesis, Characterization, and Applications in Organic Field-Effect Transistors. Organic Letters 2012, 14 (13) , 3300-3303. https://doi.org/10.1021/ol3012748
    63. Xiao-Yu Zhang and Guang-Jiu Zhao . Anisotropic Charge Transport in Bisindenoanthrazoline-Based n-Type Organic Semiconductors. The Journal of Physical Chemistry C 2012, 116 (26) , 13858-13864. https://doi.org/10.1021/jp303235x
    64. Constanza Ruiz, Eva M. García-Frutos, Gunther Hennrich, and Berta Gómez-Lor . Organic Semiconductors toward Electronic Devices: High Mobility and Easy Processability. The Journal of Physical Chemistry Letters 2012, 3 (11) , 1428-1436. https://doi.org/10.1021/jz300251u
    65. Chengliang Wang, Huanli Dong, Wenping Hu, Yunqi Liu, and Daoben Zhu . Semiconducting π-Conjugated Systems in Field-Effect Transistors: A Material Odyssey of Organic Electronics. Chemical Reviews 2012, 112 (4) , 2208-2267. https://doi.org/10.1021/cr100380z
    66. Hayden T. Black, Shubin Liu, and Valerie Sheares Ashby . Synthesis, Crystal Structures, and Electronic Properties of Nonlinear Fused Thienoacene Semiconductors. Organic Letters 2011, 13 (24) , 6492-6495. https://doi.org/10.1021/ol202662s
    67. Stefan Durben and Thomas Baumgartner . Azadibenzophospholes: Functional Building Blocks with Pronounced Electron-Acceptor Character. Inorganic Chemistry 2011, 50 (14) , 6823-6836. https://doi.org/10.1021/ic200951x
    68. Takakazu Kimoto, Kenro Tanaka, Masatoshi Kawahata, Kentaro Yamaguchi, Saika Otsubo, Yoshimasa Sakai, Yuuki Ono, Akira Ohno, and Kenji Kobayashi . Bis(methylthio)tetracenes: Synthesis, Crystal-Packing Structures, and OFET Properties. The Journal of Organic Chemistry 2011, 76 (12) , 5018-5025. https://doi.org/10.1021/jo200696a
    69. Kazuki Niimi, Shoji Shinamura, Itaru Osaka, Eigo Miyazaki, and Kazuo Takimiya . Dianthra[2,3-b:2′,3′-f]thieno[3,2-b]thiophene (DATT): Synthesis, Characterization, and FET Characteristics of New π-Extended Heteroarene with Eight Fused Aromatic Rings. Journal of the American Chemical Society 2011, 133 (22) , 8732-8739. https://doi.org/10.1021/ja202377m
    70. Di Li, Yang Yuan, Hai Bi, Dandan Yao, Xingjia Zhao, Wenjing Tian, Yue Wang, and Hongyu Zhang . Boron-Bridged π-Conjugated Ladders as Efficient Electron-Transporting Emitters. Inorganic Chemistry 2011, 50 (11) , 4825-4831. https://doi.org/10.1021/ic102554j
    71. Tomoya Kashiki, Masahiro Kohara, Itaru Osaka, Eigo Miyazaki, and Kazuo Takimiya . Synthesis and Characterization of Benzo[1,2-b:3,4-b′:5,6-b′′]trithiophene (BTT) Oligomers. The Journal of Organic Chemistry 2011, 76 (10) , 4061-4070. https://doi.org/10.1021/jo2005044
    72. Itaru Osaka, Toru Abe, Shoji Shinamura, and Kazuo Takimiya . Impact of Isomeric Structures on Transistor Performances in Naphthodithiophene Semiconducting Polymers. Journal of the American Chemical Society 2011, 133 (17) , 6852-6860. https://doi.org/10.1021/ja201591a
    73. Shoji Shinamura, Itaru Osaka, Eigo Miyazaki, Akiko Nakao, Masakazu Yamagishi, Jun Takeya, and Kazuo Takimiya . Linear- and Angular-Shaped Naphthodithiophenes: Selective Synthesis, Properties, and Application to Organic Field-Effect Transistors. Journal of the American Chemical Society 2011, 133 (13) , 5024-5035. https://doi.org/10.1021/ja110973m
    74. Xiaodong Yin, Yongjun Li, Yulan Zhu, Yuhe Kan, Yuliang Li, and Daoben Zhu . Synthesis of a Pentalene Centered Polycyclic Fused System. Organic Letters 2011, 13 (6) , 1520-1523. https://doi.org/10.1021/ol200213h
    75. Antonio Facchetti. π-Conjugated Polymers for Organic Electronics and Photovoltaic Cell Applications. Chemistry of Materials 2011, 23 (3) , 733-758. https://doi.org/10.1021/cm102419z
    76. Chia-Chun Liu, Shih-Wei Mao, and Ming-Yu Kuo . Cyanated Pentaceno[2,3-c]chalcogenophenes for Potential Application in Air-Stable Ambipolar Organic Thin-Film Transistors. The Journal of Physical Chemistry C 2010, 114 (50) , 22316-22321. https://doi.org/10.1021/jp1099464
    77. Eilaf Ahmed, Taeshik Earmme, Guoqiang Ren, and Samson A. Jenekhe . Novel n-Type Conjugated Ladder Heteroarenes: Synthesis, Self-Assembly of Nanowires, Electron Transport, and Electroluminescence of Bisindenoanthrazolines. Chemistry of Materials 2010, 22 (20) , 5786-5796. https://doi.org/10.1021/cm102147n
    78. Ho Yong Lee, Xinli Song, Hyunsoo Park, Mu-Hyun Baik and Dongwhan Lee. Torsionally Responsive C3-Symmetric Azo Dyes: Azo−Hydrazone Tautomerism, Conformational Switching, and Application for Chemical Sensing. Journal of the American Chemical Society 2010, 132 (34) , 12133-12144. https://doi.org/10.1021/ja105121z
    79. Thorsten Vehoff, Björn Baumeier, Alessandro Troisi and Denis Andrienko. Charge Transport in Organic Crystals: Role of Disorder and Topological Connectivity. Journal of the American Chemical Society 2010, 132 (33) , 11702-11708. https://doi.org/10.1021/ja104380c
    80. Yuki Suzuki, Eigo Miyazaki and Kazuo Takimiya . ((Alkyloxy)carbonyl)cyanomethylene-Substituted Thienoquinoidal Compounds: a New Class of Soluble n-Channel Organic Semiconductors for Air-Stable Organic Field-Effect Transistors. Journal of the American Chemical Society 2010, 132 (30) , 10453-10466. https://doi.org/10.1021/ja103171y
    81. Thorsten Vehoff, Yeon Sook Chung, Karen Johnston, Alessandro Troisi, Do Y. Yoon and Denis Andrienko. Charge Transport in Self-Assembled Semiconducting Organic Layers: Role of Dynamic and Static Disorder. The Journal of Physical Chemistry C 2010, 114 (23) , 10592-10597. https://doi.org/10.1021/jp101738g
    82. Itaru Osaka, Toru Abe, Shoji Shinamura, Eigo Miyazaki and Kazuo Takimiya. High-Mobility Semiconducting Naphthodithiophene Copolymers. Journal of the American Chemical Society 2010, 132 (14) , 5000-5001. https://doi.org/10.1021/ja101125p
    83. Chuan Liu, Zhihong Liu, Henrik T. Lemke, Hoi Nok Tsao, Ronald C.G. Naber, Yun Li, Kulbinder Banger, Klaus Müllen, Martin M. Nielsen and Henning Sirringhaus . High-Performance Solution-Deposited Ambipolar Organic Transistors Based on Terrylene Diimides. Chemistry of Materials 2010, 22 (6) , 2120-2124. https://doi.org/10.1021/cm902925g
    84. Shoji Shinamura, Eigo Miyazaki and Kazuo Takimiya . Synthesis, Properties, Crystal Structures, and Semiconductor Characteristics of Naphtho[1,2-b:5,6-b′]dithiophene and -diselenophene Derivatives. The Journal of Organic Chemistry 2010, 75 (4) , 1228-1234. https://doi.org/10.1021/jo902545a
    85. Chunyan Du, Jianming Chen, Yunlong Guo, Kun Lu, Shanghui Ye, Jian Zheng, Yunqi Liu, Zhigang Shuai and Gui Yu . Dicyanovinyl Heterotetracenes: Synthesis, Solid-State Structures, and Photophysical Properties. The Journal of Organic Chemistry 2009, 74 (19) , 7322-7327. https://doi.org/10.1021/jo901381f
    86. Ganapathy Balaji and Suresh Valiyaveettil. Synthesis and Properties of Symmetric and Unsymmetric Dibenzothienopyrroles. Organic Letters 2009, 11 (15) , 3358-3361. https://doi.org/10.1021/ol901133m
    87. Zuolun Zhang, Hai Bi, Yu Zhang, Dandan Yao, Hongze Gao, Yan Fan, Hongyu Zhang, Yue Wang, Yanping Wang, Zhenyu Chen and Dongge Ma . Luminescent Boron-Contained Ladder-Type π-Conjugated Compounds. Inorganic Chemistry 2009, 48 (15) , 7230-7236. https://doi.org/10.1021/ic900673s
    88. Jie-Yu Wang, Yan Zhou, Jing Yan, Lin Ding, Yuguo Ma, Yong Cao, Jian Wang and Jian Pei . New Fused Heteroarenes for High-Performance Field-Effect Transistors. Chemistry of Materials 2009, 21 (13) , 2595-2597. https://doi.org/10.1021/cm900568k
    89. Tomoya Kashiki, Shoji Shinamura, Masahiro Kohara, Eigo Miyazaki, Kazuo Takimiya, Masaaki Ikeda and Hirokazu Kuwabara. One-pot Synthesis of Benzo[b]thiophenes and Benzo[b]selenophenes from o-Halo-Substituted Ethynylbenzenes: Convenient Approach to Mono-, Bis-, and Tris-Chalcogenophene-Annulated Benzenes. Organic Letters 2009, 11 (11) , 2473-2475. https://doi.org/10.1021/ol900809w
    90. Keiichiro Kanao, Yoshihiro Miyake and Yoshiaki Nishibayashi. Ruthenium-Catalyzed Enantioselective Intramolecular Propargylation of Thiophenes with Propargylic Alcohols. Organometallics 2009, 28 (9) , 2920-2926. https://doi.org/10.1021/om9001186
    91. Amaresh Mishra, Chang-Qi Ma and Peter Bäuerle. Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications. Chemical Reviews 2009, 109 (3) , 1141-1276. https://doi.org/10.1021/cr8004229
    92. Taegweon Lee, Chad A. Landis, Bal Mukund Dhar, Byung Jun Jung, Jia Sun, Amy Sarjeant, Ho-Jin Lee and Howard E. Katz . Synthesis, Structural Characterization, and Unusual Field-Effect Behavior of Organic Transistor Semiconductor Oligomers: Inferiority of Oxadiazole Compared with Other Electron-Withdrawing Subunits. Journal of the American Chemical Society 2009, 131 (5) , 1692-1705. https://doi.org/10.1021/ja807219x
    93. Byung Jun Jung, Jia Sun, Taegweon Lee, Amy Sarjeant and Howard E. Katz. Low-Temperature-Processible, Transparent, and Air-Operable n-Channel Fluorinated Phenylethylated Naphthalenetetracarboxylic Diimide Semiconductors Applied to Flexible Transistors. Chemistry of Materials 2009, 21 (1) , 94-101. https://doi.org/10.1021/cm802281k
    94. Yongfeng Wang, Sean R. Parkin and Mark D Watson. Benzodichalcogenophenes with Perfluoroarene Termini. Organic Letters 2008, 10 (20) , 4421-4424. https://doi.org/10.1021/ol801569m
    95. Yoshitake Suzuki, Toshihiro Okamoto, Atsushi Wakamiya and Shigehiro Yamaguchi. Electronic Modulation of Fused Oligothiophenes by Chemical Oxidation. Organic Letters 2008, 10 (16) , 3393-3396. https://doi.org/10.1021/ol801136k
    96. Liqiang Li, Qingxin Tang, Hongxiang Li and Wenping Hu. Molecular Orientation and Interface Compatibility for High Performance Organic Thin Film Transistor Based on Vanadyl Phthalocyanine. The Journal of Physical Chemistry B 2008, 112 (34) , 10405-10410. https://doi.org/10.1021/jp800879g
    97. Takanobu Sanji, Kentaro Shiraishi, Taigo Kashiwabara and Masato Tanaka. Base-Mediated Cyclization Reaction of 2-Alkynylphenylphosphine Oxides: Synthesis and Photophysical Properties of Benzo[b]phosphole Oxides. Organic Letters 2008, 10 (13) , 2689-2692. https://doi.org/10.1021/ol800841v
    98. Qifan Yan, Yan Zhou, Ben-Bo Ni, Yuguo Ma, Jian Wang, Jian Pei and Yong Cao. Organic Semiconducting Materials from Sulfur-Hetero Benzo[k]fluoranthene Derivatives: Synthesis, Photophysical Properties, and Thin Film Transistor Fabrication. The Journal of Organic Chemistry 2008, 73 (14) , 5328-5339. https://doi.org/10.1021/jo800606b
    99. Jaclyn L. Brusso, Oliver D. Hirst, Afshin Dadvand, Srinivasan Ganesan, Fabio Cicoira, Craig M. Robertson, Richard T. Oakley, Federico Rosei and Dmitrii F. Perepichka. Two-Dimensional Structural Motif in Thienoacene Semiconductors: Synthesis, Structure, and Properties of Tetrathienoanthracene Isomers. Chemistry of Materials 2008, 20 (7) , 2484-2494. https://doi.org/10.1021/cm7030653
    100. Aiko Fukazawa,, Masanao Hara,, Toshihiro Okamoto,, Eun-Cheol Son,, Caihong Xu,, Kohei Tamao, and, Shigehiro Yamaguchi. Bis-Phosphoryl-Bridged Stilbenes Synthesized by an Intramolecular Cascade Cyclization. Organic Letters 2008, 10 (5) , 913-916. https://doi.org/10.1021/ol7030608
    Load more citations

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2006, 128, 39, 12604–12605
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ja064052l
    Published September 8, 2006
    Copyright © 2006 American Chemical Society

    Article Views

    8798

    Altmetric

    -

    Citations

    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.