ArticleChemistry (Weinheim an der Bergstrasse, Germany)2025
Stereodynamism in Chiral Polyaromatic Phosphepines.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
In the present experimental-computational study, we demonstrate that the stereodynamism of phosphahelicenoids can be used to afford diastereoisomers of chirally perturbed polyaromatics fused with a phosphepine ring (seven-membered P-cycle). The phosphahelicenoids have been synthesized through a stereospecific approach from commercially available BINAPs. In particular, using the combination of NMR, X-ray diffraction, and chiral HPLC experimental techniques with DFT and higher level ab initio calculations, we highlight a complex interplay between the inversion at the phosphorus stereocenter and the epimerization of the helicenoid framework, as well as a competition with a rearomatization reaction through P-extrusion. The impact of the conformational modifications on the structure have been studied through X-ray diffraction. The spectroscopic properties, in particular, of chiroptical nature, including circularly polarized luminescence, are also discussed in detail and compared to DFT and ADC(2) models.
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