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Updated: Jul 28, 2025

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Conformationally Locked Cyclo[2]Dipyrrins Linked with Anthracene Subunits: Synthesis and Chiroptical Properties
Anjana Prasad Nambiar1, Probal Nag1, Ruth Mariam Ipe1
1Department of Chemistry, Indian Institute of Science Education and Research, Thiruvananthapuram, Vithura, Maruthamala P.O., Thiruvananthapuram, 695551, India.
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 |gabs | in the order of 10-3 , and luminescence dissymmetry factors |glum | of 3.8×10-3 and 2.9×10-3 at 702 nm, respectively.
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