Highly emissive fused diarylmaleimides synthesized by a cascade reaction of selective bromination and visible-light-driven cyclization. (March 2021)

• Record Type: Journal Article
• Authors: Zheng, Xin; Wang, Jingwei; Xiao, Duoduo; Chen, Huan; Lin, Zhenghuan; Ling, Qidan
• Is Part Of: Dyes and pigments. Volume 187(2021)
• Publication Date: 2021-03
• Subjects: Diarylmaleimide -- Cyclization -- Visible light-driven -- Emission -- Bromination; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2020.109113
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: A simple strategy for constructing fused diarylmaleimides (FAMs) under mild condition is presented through a cascade reaction involving a selective bromination with NBS and a visible-light-driven cyclization under 18 W of LED. Compared with traditional oxidation method, the cascade reaction does not use any oxidant, metal-based catalyst, and ultraviolet rays. According to the strategy, a series of symmetrical and asymmetrical FAMs with different aromatic rings are obtained in high yield up to 96%. Most of FAMs exhibit blue-shifted emission and higher luminescent efficiency ( Φ f up to 84%) in solution than their open-ring counterparts for the large π-conjugated systems weakening intramolecular charge transfer. Unexpectedly, the fused rings with nearly coplanar do not quench the solid-state fluorescence of FAMs, due to the heteroatoms and peripheral substituents inhibiting molecules forming H-aggregation-like tight packing, resulting in decent quantum yield in solid. Particularly, FAM with indolo [2, 3-a] pyrrolo [3, 4-c] carbazoles (B3IM-BHc) has unique pores in the crystal structure, which imposes it huge potential as smart florescent material and switch. Graphical abstract: Image 1 Highlights: A cascade reaction is used to construct fused diarylmaleimides (FAMs) under mild condition. The cascade reaction involves selective bromination and visible-light-driven cyclization. A series of FAMs with different aromatic rings are obtained in high yield up to 96%. FAMs show higher Φ f (up to 84%) in solution than their open-ring counterparts. Fused rings with nearly coplanar do not quench the solid-state fluorescence of FAMs.