Induction of chirality in 4,4′-azopyridine by halogen-bonding interaction with optically active ditopic donors

Optically active ditopic halogen bond donors bearing two 4-iodotetrafluorophenyl groups were obtained by reaction of chiral diols with iodopentafluorobenzene. Co-crystallization of these donors with anti -4,4′-azopyridine afforded binary complexes containing infinite chains of the alternating compon...

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Bibliographic Details
Published in:New journal of chemistry 2019-04, Vol.43 (14), p.5512-5517
Main Authors: Alfuth, Jan, Chojnacki, Jaros aw, Po o ski, Tadeusz, Olszewska, Teresa
Format: Article
Language:English
Subjects:
Aromatic compounds
Chiral dynamics
Chirality
Chromophores
Crystal structure
Crystallization
Crystallography
Diols
Donors (electronic)
NMR
Nuclear magnetic resonance
Optical activity
Perturbation
Twisting
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Summary:Optically active ditopic halogen bond donors bearing two 4-iodotetrafluorophenyl groups were obtained by reaction of chiral diols with iodopentafluorobenzene. Co-crystallization of these donors with anti -4,4′-azopyridine afforded binary complexes containing infinite chains of the alternating component molecules connected by halogen bonds. The solid state CD measurements confirmed that complexation induces optical activity of the azo chromophore due to the twisting of the aryl-N&z.dbd;N system or external chiral perturbation exerted by host molecules. Co-crystallization of 4,4′-azopyridine with optically active halogen-bonding donors results in induction of chirality in this molecule.
ISSN:1144-0546
1369-9261
DOI:10.1039/c8nj05750h