Chiral Teropyrenes: Synthesis, Structure, and Spectroscopic Studies

We present the inaugural synthesis of a chiral teropyrene achieved through a four-fold alkyne benzannulation catalyzed by InCl3, resulting in good yields. The product underwent thorough characterization using FT-Raman and FT-IR spectroscopies, demonstrating a close agreement with calculated spectra. X-ray crystallographic analysis unveiled a notable twist in the molecule's backbone, with an end-to-end twist angle of 51 degrees, consistent with computational predictions. Experimentally determined enantiomeric inversion barriers revealed a significant energy barrier of 23 kcal/mol, facilitating the isolation of enantiomers for analysis by circular dichroism (CD) and circularly polarized luminescence (CPL) spectroscopies. These findings mark significant strides in the synthesis and characterization of chiral teropyrenes, offering insights into their structural and spectroscopic properties.The synthesis of a chiral teropyrene was achieved through a four-fold alkyne benzannulation, leveraging InCl3 catalysis. This compound exhibits both circular dichroism (CD) and circularly polarized luminescence (CPL) properties, underscoring its significance in advancing chiral optoelectronic materials. image