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Title: Extended π-conjugated pyrene derivatives: structural, photophysical and electrochemical properties
Authors: Feng, Xing
Seto, Nobuyuki
Wang, Chuan-Zeng
Matsumoto, Taisuke
Tanaka, Junji
Wei, Xian-Fu
Elsegood, Mark R.J.
Horsburgh, Lynne
Redshaw, Carl
Yamato, Takehiko
Keywords: Pyrenes
Intramolecular charge-transfer
Single crystals
Luminescence material
Structure-property relationship
Issue Date: 2016
Publisher: © Wiley
Citation: FENG, X. ... et al, 2016. Extended π-conjugated pyrene derivatives: structural, photophysical and electrochemical properties. ChemistrySelect, 1 (9), pp. 1926-1932.
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.
Description: This paper is closed access until 16th June 2017.
Sponsor: This work was performed under the Cooperative Research Program of “Network Joint Research Center for Materials and Devices (Institute for Materials Chemistry and Engineering, Kyushu University)”. We also would like to thank the EPSRC (overseas travel grant to C.R.), The Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry and The Scientific Research Common Program of Beijing Municipal Commission of Education for financial support (18190115/008).
Version: Accepted for publication
DOI: 10.1002/slct.201600598
URI: https://dspace.lboro.ac.uk/2134/23384
Publisher Link: http://dx.doi.org/10.1002/slct.201600598
ISSN: 2365-6549
Appears in Collections:Closed Access (Chemistry)

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