A–π–D–π–A carbazole derivatives with remarkable solvatochromism and mechanoresponsive luminescence turn-on. Issue 25 (18th May 2017)

• Record Type: Journal Article
• Authors: Wen, Ping; Gao, Zhixiang; Zhang, Rong; Li, Anran; Zhang, Fang; Li, Jie; Xie, Jingjuan; Wu, Yuezhen; Wu, Min; Guo, KunPeng
• Is Part Of: Journal of materials chemistry. Volume 5:Issue 25(2017)
• Page Start: 6136
• Page End: 6143
• Publication Date: 2017-05-18
• Subjects: Materials -- Periodicals; Chemistry, Analytic -- Periodicals; Optical materials -- Research -- Periodicals; Electronics -- Materials -- Research -- Periodicals; 543.0284
• DOI: 10.1039/c7tc00559h
• Languages: English
• ISSNs: 2050-7526

Abstract

Abstract : Two A–π–D–π–A carbazole derivatives differing in N -hexyl and N -isooctyl substituents were developed. They exhibited a prominent solvatochromic effect and luminescence turn-on characteristics under mechanical force stimuli. Abstract : Two A–π–D–π–A molecules with a carbazole donor and a dicyanovinyl acceptor but differing in N -hexyl ( h -CPDM ) and N -isooctyl substituents ( i -CPDM ) were synthesized, and both of them presented remarkable dual properties of solvatochromism and mechanoresponsive luminescence (MRL) turn-on. The intrinsic intramolecular charge transfer (ICT) characteristic endowed both luminophors with a prominent solvatochromic effect, with emission color tuning from blue to orange-red by changing the solvent from nonpolar hexane to polar dimethyl sulfoxide. Meanwhile, the non-/weakly emissive original powders of h -CPDM and i -CPDM gave bright orange (610 nm) and yellow (596 nm) emission with the photoluminescence quantum yields increasing as high as 85-fold after being ground. Investigations revealed this mechanoresponsive luminescence turn-on could be ascribed to the disturbance of the π–π stacking interactions in the non-/weakly emissive J-aggregates by mechanical force. This work offers carbazole derivatives that can be used as sensitive fluorescent indicators for organic solvents and mechanical sensors.