Conformationally Locked Cyclo[2]Dipyrrins Linked with Anthracene Subunits: Synthesis and Chiroptical Properties

被引：4
|
作者：
Prasad Nambiar, Anjana [1 ]
Nag, Probal [1 ]
Mariam Ipe, Ruth [1 ]
Reddy Vennapusa, Sivaranjana [1 ]
Gokulnath, Sabapathi [1 ]
机构：
[1] Indian Inst Sci Educ & Res, Dept Chem, Thiruvananthapuram 695551, India
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 30期
关键词：
Chirality; Circularly Polarized Luminescence; Conformation; Helical Enantiomers; Porphyrinoids; AROMATICITY; CHIRALITY;
D O I：
10.1002/anie.202306566
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Herein, we report the synthesis of anthracene-containing twisted cyclo[2]dipyrrin 1 by utilizing a non-planar building block, 1,5-dipyrrylanthracene (1,5-DPA). The non-planar nature of the macrocycle enhanced the solubility and helped in structural characterization. Macrocycle 1 adopts a twisted 'figure of eight' conformation stabilized by strong intramolecular H-bonding interactions and exists as a pair of helical enantiomers, as revealed by X-ray crystallographic analysis. More importantly, the sterically locked structure enabled facile optical resolution using chiral HPLC. The (P,P) and (M,M) enantiomers show moderate chiroptical properties, such as absorption dissymmetry factors |g(abs)| in the order of 10(-3), and luminescence dissymmetry factors |g(lum)| of 3.8x10(-3) and 2.9x10(-3) at 702 nm, respectively.
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页数：5
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