Literature DB >> 22717444

The synthesis, crystal structure and charge-transport properties of hexacene.

Motonori Watanabe1, Yuan Jay Chang, Shun-Wei Liu, Ting-Han Chao, Kenta Goto, Md Minarul Islam, Chih-Hsien Yuan, Yu-Tai Tao, Teruo Shinmyozu, Tahsin J Chow.   

Abstract

Acenes can be thought of as one-dimensional strips of graphene and they have the potential to be used in the next generation of electronic devices. However, because acenes larger than pentacene have been found to be unstable, it was generally accepted that they would not be particularly useful materials under normal conditions. Here, we show that, by using a physical vapour-transport method, platelet-shaped crystals of hexacene can be prepared from a monoketone precursor. These crystals are stable in the dark for a long period of time under ambient conditions. In the crystal, the molecules are arranged in herringbone arrays, quite similar to that observed for pentacene. A field-effect transistor made using a single crystal of hexacene displayed a hole mobility significantly higher than that of pentacene. This result suggests that it might be instructive to further explore the potential of other higher acenes.

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Year:  2012        PMID: 22717444     DOI: 10.1038/nchem.1381

Source DB:  PubMed          Journal:  Nat Chem        ISSN: 1755-4330            Impact factor:   24.427


  22 in total

1.  Control of carrier density by self-assembled monolayers in organic field-effect transistors.

Authors:  S Kobayashi; T Nishikawa; T Takenobu; S Mori; T Shimoda; T Mitani; H Shimotani; N Yoshimoto; S Ogawa; Y Iwasa
Journal:  Nat Mater       Date:  2004-04-04       Impact factor: 43.841

2.  Conducting AFM and 2D GIXD studies on pentacene thin films.

Authors:  Hoichang Yang; Tae Joo Shin; Mang-Mang Ling; Kilwon Cho; Chang Y Ryu; Zhenan Bao
Journal:  J Am Chem Soc       Date:  2005-08-24       Impact factor: 15.419

3.  Molecular motion in crystalline naphthalene: analysis of multi-temperature X-ray and neutron diffraction data.

Authors:  Silvia C Capelli; Alberto Albinati; Sax A Mason; Bertram T M Willis
Journal:  J Phys Chem A       Date:  2006-10-19       Impact factor: 2.781

4.  A new type of soluble pentacene precursor for organic thin-film transistors.

Authors:  Kew-Yu Chen; Hsing-Hung Hsieh; Chung-Chih Wu; Jiunn-Jye Hwang; Tahsin J Chow
Journal:  Chem Commun (Camb)       Date:  2006-12-14       Impact factor: 6.222

5.  Polymorphism in pentacene.

Authors:  C C Mattheus; A B Dros; J Baas; A Meetsma; J L de Boer; T T Palstra
Journal:  Acta Crystallogr C       Date:  2001-08-09       Impact factor: 1.172

6.  Design, synthesis, and characterization of a persistent nonacene derivative.

Authors:  Irvinder Kaur; Mikael Jazdzyk; Nathan N Stein; Polina Prusevich; Glen P Miller
Journal:  J Am Chem Soc       Date:  2010-02-03       Impact factor: 15.419

7.  Photodecarbonylation of alpha-diketones: a mechanistic study of reactions leading to acenes.

Authors:  Rajib Mondal; Albert N Okhrimenko; Bipin K Shah; Douglas C Neckers
Journal:  J Phys Chem B       Date:  2007-12-11       Impact factor: 2.991

8.  The larger acenes: versatile organic semiconductors.

Authors:  John E Anthony
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

9.  Exploiting substituent effects for the synthesis of a photooxidatively resistant heptacene derivative.

Authors:  Irvinder Kaur; Nathan N Stein; Ryan P Kopreski; Glen P Miller
Journal:  J Am Chem Soc       Date:  2009-03-18       Impact factor: 15.419

10.  Substituent effects in pentacenes: gaining control over HOMO-LUMO gaps and photooxidative resistances.

Authors:  Irvinder Kaur; Wenling Jia; Ryan P Kopreski; Selvapraba Selvarasah; Mehmet R Dokmeci; Chandrani Pramanik; Nicol E McGruer; Glen P Miller
Journal:  J Am Chem Soc       Date:  2008-12-03       Impact factor: 15.419

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  22 in total

1.  Conductance saturation in a series of highly transmitting molecular junctions.

Authors:  T Yelin; R Korytár; N Sukenik; R Vardimon; B Kumar; C Nuckolls; F Evers; O Tal
Journal:  Nat Mater       Date:  2016-02-01       Impact factor: 43.841

Review 2.  Synthesis of oligoacenes using precursors for evaluation of their electronic structures.

Authors:  Hiroko Yamada; Hironobu Hayashi
Journal:  Photochem Photobiol Sci       Date:  2022-06-07       Impact factor: 4.328

3.  Synthesis and physical properties of brominated hexacene and hole-transfer properties of thin-film transistors.

Authors:  Motonori Watanabe; Takaaki Miyazaki; Toshinori Matsushima; Junko Matsuda; Ching-Ting Chein; Masahiko Shibahara; Chihaya Adachi; Shih-Sheng Sun; Tahsin J Chow; Tatsumi Ishihara
Journal:  RSC Adv       Date:  2018-04-10       Impact factor: 4.036

4.  An Approach to the Synthesis of Functionalized Polycyclic Aromatic Hydrocarbons.

Authors:  Mark Little; He Lan; James Raftery; John J Morrison; Joseph J W McDouall; Stephen G Yeates; Peter Quayle
Journal:  European J Org Chem       Date:  2013-08-09

Review 5.  Strategies for the Synthesis of Higher Acenes.

Authors:  Ruth Dorel; Antonio M Echavarren
Journal:  European J Org Chem       Date:  2016-11-16

6.  Higher Acenes by On-Surface Dehydrogenation: From Heptacene to Undecacene.

Authors:  Rafal Zuzak; Ruth Dorel; Marek Kolmer; Marek Szymonski; Szymon Godlewski; Antonio M Echavarren
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-07       Impact factor: 15.336

7.  Synthesis, crystal structure and charge transport characteristics of stable peri-tetracene analogues.

Authors:  Masashi Mamada; Ryota Nakamura; Chihaya Adachi
Journal:  Chem Sci       Date:  2020-10-14       Impact factor: 9.825

8.  Crystal design using multipolar electrostatic interactions: A concept study for organic electronics.

Authors:  Peer Kirsch; Qiong Tong; Harald Untenecker
Journal:  Beilstein J Org Chem       Date:  2013-11-05       Impact factor: 2.883

9.  An extended phenacene-type molecule, [8]phenacene: synthesis and transistor application.

Authors:  Hideki Okamoto; Ritsuko Eguchi; Shino Hamao; Hidenori Goto; Kazuma Gotoh; Yusuke Sakai; Masanari Izumi; Yutaka Takaguchi; Shin Gohda; Yoshihiro Kubozono
Journal:  Sci Rep       Date:  2014-06-17       Impact factor: 4.379

10.  A method for controlling the synthesis of stable twisted two-dimensional conjugated molecules.

Authors:  Yongjun Li; Zhiyu Jia; Shengqiang Xiao; Huibiao Liu; Yuliang Li
Journal:  Nat Commun       Date:  2016-05-16       Impact factor: 14.919

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