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Extended π-conjugated pyrene derivatives: structural, photophysical and electrochemical properties

Feng, Xing; Seto, Nobuyuki; Wang, Chuan-Zeng; Matsumoto, Taisuke; Tanaka, Junji; Wei, Xian-Fu; Elsegood, Mark R.J.; Horsburgh, Lynne; Redshaw, Carl; Yamato, Takehiko

Authors

Xing Feng

Nobuyuki Seto

Chuan-Zeng Wang

Taisuke Matsumoto

Junji Tanaka

Xian-Fu Wei

Mark R.J. Elsegood

Lynne Horsburgh

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Professor Carl Redshaw C.Redshaw@hull.ac.uk
Professor of Inorganic Materials Chemistry and REF Lead for Chemistry

Takehiko Yamato



Abstract

This article presents a set of extended π-conjugated pyrene derivatives, namely 1,3-di(arylethynyl)-7-tert-butylpyrenes, which were synthesized by a Pd-catalyzed Sonogashira coupling reaction of 1,3-dibromo-7-tert-butylpyrenes with the corresponding arylethynyl group in good yields. Despite the presence of the tert-butyl group located at the 7-position of pyrene, X-ray crystallographic analyses show that the planarity of the Y-shaped molecules still exhibits strong face-to-face π-π stacking in the solid state; all of the compounds exhibit blue or green emission with high quantum yields (QYs) in dichloromethane. DFT calculations and electrochemistry revealed that this category of compound possesses hole-transporting characteristics. In addition, with strong electron-donating (-N(CH₃)₂) or electron-withdrawing (-CHO) groups in 2 d or 2 f, these molecules displayed efficient intramolecular charge-transfer (ICT) emissions with solvatochromic shifts from blue to yellow (green) on increasing the solvent polarity. Furthermore, the compounds 2 d and 2 f possess strong CT characteristics.

Citation

Feng, X., Seto, N., Wang, C., Matsumoto, T., Tanaka, J., Wei, X., …Yamato, T. (2016). Extended π-conjugated pyrene derivatives: structural, photophysical and electrochemical properties. ChemistrySelect, 1(9), 1926-1932. https://doi.org/10.1002/slct.201600598

Journal Article Type Article
Acceptance Date May 25, 2016
Online Publication Date Jun 21, 2016
Publication Date Jun 16, 2016
Deposit Date Nov 17, 2016
Publicly Available Date Mar 28, 2024
Journal ChemistrySelect
Electronic ISSN 2365-6549
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 1
Issue 9
Pages 1926-1932
DOI https://doi.org/10.1002/slct.201600598
Keywords Pyrenes
Public URL https://hull-repository.worktribe.com/output/445352
Publisher URL http://onlinelibrary.wiley.com/doi/10.1002/slct.201600598/abstract;jsessionid=A65A3B19362925C2974E3D69883F7CD9.f04t01
Additional Information This is the peer reviewed version of the following article: X. Feng , N. Seto, C.-Z. Wang, T. Matsumoto, J. Tanaka, X.-F. Wei, M. R. J. Elsegood, L. Horsburgh, C. Redshaw, T. Yamato, ChemistrySelect 2016, 1, 1926, which has been published in final form at http://dx.doi.org/10.1002/slct.201600598 . This article may be used for non-commercial purposes in accordance With Wiley Terms and Conditions for self-archiving.

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