N-fused ring strategy toward orange/yellow light-emitting liquid crystalline molecules

• Published in: Dyes and pigments Vol. 159; pp. 115 - 120
• Main Authors: Liu, Tingting, Zhu, Dezhao, Zhang, Mei, Cui, Ming, Li, Qingfang, Fan, Yanmei, Wang, Hui, Zeng, Zhuo
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 01.12.2018
• Subjects: Fluorinated N-Fused ring; Liquid crystal; Luminescene; Tuned emitting color; Fluorinated N-Fused ring; Tuned emitting color; Liquid crystal; Luminescene
• ISSN: 0143-7208; 1873-3743
• DOI: 10.1016/j.dyepig.2018.06.016

A new synthetic procedure for fluorinated N-fused ring, 2F-fluorazone (1,2-difluoro-9H-pyrrolo[1,2]-indol-9-one), has been developed. It connected with acetylene to obtain the first example of fluorinated N-fused rings luminescent liquid crystals (LLCs). CH3O-fluorazone-2F and CH3O-fluorazone display yellow and orange fluorescence respectively, and their properties can be tuned by the substitution pattern. A new synthetic procedure for fluorinated fused ring, 2F-fluorazone (1,2-difluoro-9H-pyrrolo[1,2]-indol-9-one), has been developed. The fused ring, 2F-fluorazone and fluorazone, can replace the traditional macrocycles to obtain the first D-π-A type luminescent liquid crystals (LLCs), which emit yellow–to-orange fluorescence and their properties can be tuned by the substitution pattern. [Display omitted] •New fluorinated N-fused ring, 2F-fluorazone (1,2-difluoro-9H-pyrrolo[1,2]-indol-9-one), has been synthesized.•The first fluorinated N-fused ring-based luminescent liquid crystals with 2F-fluorazone as terminal were developed.•Their photoluminescence wavelength and emitted color can be tuned by the substitution pattern.•Fluorinated fused ring increase the (C-H···O/π) weak interactions and prevent the π−π stacking interactions.•A simple and straightforward route to obtain yellow/orange luminescent liquid crystals.