STEREOCHEMICAL FEATURES OF REPRODUCING A STABLE DIMERIC MOTIF IN THE CRYSTALS OF BODIPY DERIVATIVES IN TRANSITIONING FROM AN ACHIRAL TO A CHIRAL SUBSTITUTE IN MESO-POSITION

The paper considers supramolecular organization of molecules in the crystals of two luminophores, derivatives of the family of fluorinated boron-dipyrromethene complexes (BODIPY) differing by the substituent in the meso -position of the indacene core. It is shown that a stable dimeric motif is trans...

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Bibliographic Details
Published in:Journal of structural chemistry 2022-12, Vol.63 (12), p.1913-1922
Main Authors: Frantsuzova, L. V., Gerasimova, D. P., Lodochnikova, O. A.
Format: Article
Language:English
Subjects:
Atomic
Atomic/Molecular Structure and Spectra
Chemistry
Chemistry and Materials Science
Crystals
Dimers
Electron density
Inorganic Chemistry
Mathematical analysis
Molecular
Optical and Plasma Physics
Physical Chemistry
Quantum chemistry
Solid State Physics
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Summary:The paper considers supramolecular organization of molecules in the crystals of two luminophores, derivatives of the family of fluorinated boron-dipyrromethene complexes (BODIPY) differing by the substituent in the meso -position of the indacene core. It is shown that a stable dimeric motif is transferred from the racemic crystal to the chiral one to form two supramolecular diastereomers in the latter case. Quantum chemical DFT calculations along with the topological analysis of the calculated electron density reveal that C–H⋯F interactions play a leading role in the formation of these dimers; a presence of weaker intradimer interactions C–H⋯π, C–H⋯O, and π⋯π is demonstrated.
ISSN:0022-4766
1573-8779
DOI:10.1134/S0022476622120010