In:
Angewandte Chemie, Wiley, Vol. 135, No. 8 ( 2023-02-13)
Abstract:
It is essential to create organic compounds that exhibit circularly polarized luminescence (CPL) in the near‐infrared (NIR) range. Helicene‐type emitters possess appealing chiroptical features, however, such NIR molecules are scarce due to a paucity of synthetic strategies. Herein, we developed a series of helical β‐isoindigo‐based B−O−B bridged aza‐BODIPY analogs that were synthesized conveniently. The reaction of diimino‐β‐isoindigo with a heteroaromatic amine produced a restricted ligand cavity, which triggered off the generation of a B−O−B bridge. The B−O−B bridge led to distorted conformations that satisfy the helical requirements, resulting in excellent spectroscopic and chiroptical properties. Tunable CPL with the highest luminescence dissymmetry factor ( g lum ) of 1.3×10 −3 and a CPL brightness ( B CPL =11.5 M −1 cm −1 ) in the NIR region was achieved. This synthetic approach is expected to offer a new opportunity to chiral chemistry and increase flexibility for chiroptical tuning.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.202218023
Language:
English
Publisher:
Wiley
Publication Date:
2023
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