Citation: Yang Zhang, Juejun Wang, Hongming Chen, Meijin Lin. 1, 1′-Binaphthol annulated perylene diimides: Aggregation-induced emission enhancement and chirality inversion[J]. Chinese Chemical Letters, ;2022, 33(5): 2473-2476. doi: 10.1016/j.cclet.2021.11.069 shu

1, 1′-Binaphthol annulated perylene diimides: Aggregation-induced emission enhancement and chirality inversion

Yang Zhang ^a ,
Juejun Wang ^a ,
Hongming Chen ^b ,
Meijin Lin ^{a, b, *,}

a.
Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, Fuzhou 350116, China
b.
College of Materials Science and Engineering, Fuzhou University, Fuzhou 350116, China

meijin_lin@fzu.edu.cn

Received Date: 29 July 2021
Revised Date: 22 November 2021
Accepted Date: 23 November 2021
Available Online: 27 November 2021

Figures(8)

Aggregation-induced emission enhancement and aggregation-induced chirality inversion are two individual phenomena for the enantiomerically pure organic dyes in the aggregates. Herein we reported for the first time that these two interesting phenomena could be observed simultaneously in the aggregated states of enantiomerically pure S/R-1, 1′-binaphthol annulated perylene diimides, in which two perylene diimides moieties were bridged by S/R-1, 1′-binaphthol (BINOL) at the bay positions. Owing to the rotatable C2 axes between two naphthol annulated perylene diimides moieties, both of them display intrinsic behaviors of aggregation-induced emission enhancements. At the same time, due to the steric hindrances in the imide and methoxy positions, the neighboring two π-systems of these two unique polycyclic aromatic imides in poor solvents are preferable to adopt a cross-stacking mode and thus form helical X-aggregates of opposite chirality (M/P) with chirality inversion characteristics in their circular dichroism and circularly polarized luminescence spectroscopic studies.
- Perylene diimides,
- 1, 1′-Binaphthol,
- Aggregation-induced emission enhancement,
- Chirality inversion
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