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Hirayama S, Sakai H, Araki Y, et al. Systematic control of the excited-state dynamics and carrier-transport properties of functionalized benzo[ghi]perylene and coronene derivatives. Chemistry. 2014;20(29):9081-93doi: 10.1002/chem.201304679.
Hirayama, S., Sakai, H., Araki, Y., Tanaka, M., Imakawa, M., Wada, T., Takenobu, T., & Hasobe, T. (2014). Systematic control of the excited-state dynamics and carrier-transport properties of functionalized benzo[ghi]perylene and coronene derivatives. Chemistry (Weinheim an der Bergstrasse, Germany), 20(29), 9081-93. https://doi.org/10.1002/chem.201304679
Hirayama, Sunao, et al. "Systematic control of the excited-state dynamics and carrier-transport properties of functionalized benzo[ghi]perylene and coronene derivatives." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 20,29 (2014): 9081-93. doi: https://doi.org/10.1002/chem.201304679
Hirayama S, Sakai H, Araki Y, Tanaka M, Imakawa M, Wada T, Takenobu T, Hasobe T. Systematic control of the excited-state dynamics and carrier-transport properties of functionalized benzo[ghi]perylene and coronene derivatives. Chemistry. 2014 Jul 14;20(29):9081-93. doi: 10.1002/chem.201304679. Epub 2014 Jun 20. PMID: 24953934.
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Chemistry. 2014 Jul 14;20(29):9081-93. doi: 10.1002/chem.201304679. Epub 2014 Jun 20.

Systematic control of the excited-state dynamics and carrier-transport properties of functionalized benzo[ghi]perylene and coronene derivatives.

Chemistry (Weinheim an der Bergstrasse, Germany)

Sunao Hirayama, Hayato Sakai, Yasuyuki Araki, Minako Tanaka, Masaki Imakawa, Takehiko Wada, Taishi Takenobu, Taku Hasobe

Affiliations

  1. Department of Chemistry, Faculty of Science and Technology, Keio University, Yokohama, Kanagawa 223-8522 (Japan), Fax: (+81)?45-566-1697.

PMID: 24953934 DOI: 10.1002/chem.201304679

Abstract

A series of benzo[ghi]perylene (Bp) and coronene (Cor) derivatives substituted with electron-withdrawing methoxycarbonyl (COOMe) or electron-donating methoxyl (MeO) groups was synthesized. The electrochemical, spectroscopic, and photophysical properties of these compounds were investigated by cyclic voltammetry, steady-state and time-resolved spectroscopy, and quantum-yield measurements. Introduction of suitable substituents onto the aromatic rings enabled control of electrochemical and spectroscopic behavior. Examination of excited-state dynamics revealed that fluorescence quantum yields increased with increasing number of COOMe groups in both Bp and Cor derivatives, consistent with the findings of DFT calculations. Single-crystal analysis allowed the performance of field-effect transistors containing single crystals of the derivatives to be rationalized.

© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: device fabrication; electrochemistry; fluorescence; polycycles; solid-state structures

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