Chiral Teropyrenes: Synthesis, Structure, and Spectroscopic Studies.
Angew Chem Int Ed Engl
; 63(33): e202404849, 2024 Aug 12.
Article
em En
| MEDLINE
| ID: mdl-38818567
ABSTRACT
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°, consistent with computational predictions. Experimentally determined enantiomeric inversion barriers revealed a significant energy barrier of 23â
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.
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MEDLINE
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En
Ano de publicação:
2024
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Article