2134/23384
Xing Feng
Xing
Feng
Nobuyuki Seto
Nobuyuki
Seto
Chuan-Zeng Wang
Chuan-Zeng
Wang
Taisuke Matsumoto
Taisuke
Matsumoto
Junji Tanaka
Junji
Tanaka
Xian-Fu Wei
Xian-Fu
Wei
Mark Elsegood
Mark
Elsegood
Lynne Horsburgh
Lynne
Horsburgh
Carl Redshaw
Carl
Redshaw
Takehiko Yamato
Takehiko
Yamato
Extended [pi]-conjugated pyrene derivatives: structural, photophysical and electrochemical properties
Loughborough University
2016
Pyrenes
Intramolecular charge-transfer
Single crystals
Luminescence material
Structure-property relationship
Chemical Sciences not elsewhere classified
2016-12-08 12:14:28
Journal contribution
https://repository.lboro.ac.uk/articles/journal_contribution/Extended_pi_-conjugated_pyrene_derivatives_structural_photophysical_and_electrochemical_properties/9393896
This article presents a set of extended [pi]-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 [pi]-[pi] 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.