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Helical β‐isoindigo‐Based Chromophores with B−O−B Bridge: Facile Synthesis and Tunable Near‐Infrared Circularly Polarized Luminescence

2022; Wiley; Volume: 62; Issue: 8 Linguagem: Inglês

10.1002/anie.202218023

1521-3773

Yongqiang Xu, Zhigang Ni, Yao Xiao, Ziwei Chen, Sisi Wang, Lizhi Gai, You‐Xuan Zheng, Zhen Shen, Hua Lü, Zijian Guo,

Polydiacetylene-based materials and applications

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 (glum ) of 1.3×10-3 and a CPL brightness (BCPL =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.