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Abstract 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 3.8×10 −3 and 2.9×10 −3 at 702 nm, respectively.
Nambiar et al. (Wed,) studied this question.