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.