Synthesis of fluoro- and cyano-aryl containing pyrene derivatives and their optical and electrochemical properties

Gong, Xiaojie; Heeran, Darren; Zhao, Qiang; Zheng, Chaoyue; Yufit, Dmitry S.; Sandford, Graham; Gao, Deqing

doi:10.1002/ajoc.201900018

Synthesis of fluoro- and cyano-aryl containing pyrene derivatives and their optical and electrochemical properties

Gong, Xiaojie; Heeran, Darren; Zhao, Qiang; Zheng, Chaoyue; Yufit, Dmitry S.; Sandford, Graham; Gao, Deqing

Authors

Xiaojie Gong

Darren Heeran

Qiang Zhao

Chaoyue Zheng

Dmitry S. Yufit

Graham Sandford

Deqing Gao

Abstract

Mono‐ and 1,6‐disubstituted pyrene derivatives bearing perfluorotoluene or perfluorobenzonitrile moieties were synthesized by nucleophilic substitution processes. The compounds were characterized by NMR, UV‐vis, photoluminescence (PL), thermal gravimetric analysis (TGA), differential scanning calorimetry (DSC), cyclic voltametry (CV) and density functional theory (DFT) calculations. We found that derivatives substituted with perfluorobenzonitrile showed better thermal stability, stronger electron with‐drawing ability and better fluorescence properties than the corresponding perfluorotoluyl‐pyrene systems

Citation

Gong, X., Heeran, D., Zhao, Q., Zheng, C., Yufit, D. S., Sandford, G., & Gao, D. (2019). Synthesis of fluoro- and cyano-aryl containing pyrene derivatives and their optical and electrochemical properties. Asian Journal of Organic Chemistry, 8(5), 722-730. https://doi.org/10.1002/ajoc.201900018

Journal Article Type	Article
Acceptance Date	Feb 11, 2019
Online Publication Date	Feb 12, 2019
Publication Date	May 31, 2019
Deposit Date	Feb 14, 2019
Publicly Available Date	Feb 12, 2020
Journal	Asian Journal of Organic Chemistry
Print ISSN	2193-5807
Electronic ISSN	2193-5815
Publisher	Wiley
Peer Reviewed	Peer Reviewed
Volume	8
Issue	5
Pages	722-730
DOI	https://doi.org/10.1002/ajoc.201900018

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Copyright Statement
This is the accepted version of the following article: Gong, Xiaojie, Heeran, Darren, Zhao, Qiang, Zheng, Chaoyue, Yufit, Dmitry S., Sandford, Graham & Gao, Deqing (2019). Synthesis of fluoro- and cyano-aryl containing pyrene derivatives and their optical and electrochemical properties. Asian Journal of Organic Chemistry 8(5): 722-730 which has been published in final form at https://doi.org/10.1002/ajoc.201900018. This article may be used for non-commercial purposes in accordance With Wiley Terms and Conditions for self-archiving.