Xing Feng
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
Nobuyuki Seto
Chuan-Zeng Wang
Taisuke Matsumoto
Junji Tanaka
Xian-Fu Wei
Mark R.J. Elsegood
Lynne Horsburgh
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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