Modulation of the cis‐ and trans‐Conformations in Bis‐o‐carborane Substituted Benzodithiophenes and Emission Enhancement Effect on Luminescent Efficiency by Solidification. Issue 12 (30th March 2018)

• Record Type: Journal Article
• Authors: Nishino, Kenta; Uemura, Kyoya; Tanaka, Kazuo; Morisaki, Yasuhiro; Chujo, Yoshiki
• Is Part Of: European journal of organic chemistry. Issue 12(2018)
• Page Start: 1507
• Page End: 1512
• Publication Date: 2018-03-30
• Subjects: Carboranes -- Aggregation‐induced emission -- Solid‐state structures -- Luminescence; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201701641
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Bis‐carborane‐substituted benzo[1, 2‐ b :4, 5‐ b′ ]dithiophenes (DCB‐R, where R = H, t Bu) were synthesized and characterized. Their three‐dimensional conformations were tuned by introducing the tert ‐butyl substituent at the para ‐positions of the phenyl rings. Both molecules showed emission enhancement behavior, especially in the solid state. The emission quantum efficiencies were over 0.90 in the crystalline state. Moreover, it was shown that the efficiency of DCB‐ t Bu was over 0.70 in the amorphous state. From structural analyses and mechanistic investigations, it was proposed that the tert ‐butyl substituents play a critical role in the formation of the trans ‐conformation followed by suppression of aggregation‐caused quenching because of the o ‐carborane units located at each plane of the benzodithiophene ring. Abstract : Bis‐carborane‐substituted benzodithiophenes with or without tert ‐butyl substituents were synthesized. It was found that their three‐dimensional conformations were tuned by introducing the tert ‐butyl substituent. Both molecules showed emission enhancement behavior, especially in the solid state.