Diastereoselective supramolecular ion-pairing between the TRISPHAT anion and pro-chiral heptamethine cyanine dyes | Zendy

PierreAntoine Bouit | Zendy; C. Aronica | Zendy; Laure Guy | Zendy; Alexandre Martinez | Zendy; Chantal Andraud | Zendy; Olivier Maury | Zendy

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Diastereoselective supramolecular ion-pairing between the TRISPHAT anion and pro-chiral heptamethine cyanine dyes

Author(s) -

PierreAntoine Bouit,

C. Aronica,

Laure Guy,

Alexandre Martinez,

Chantal Andraud,

Olivier Maury

Publication year - 2009

Publication title -

organic and biomolecular chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.923

H-Index - 146

eISSN - 1477-0539

pISSN - 1477-0520

DOI - 10.1039/b905366b

Subject(s) - cyanine , enantiopure drug , supramolecular chemistry , chirality (physics) , chemistry , molecule , ion , stereochemistry , photochemistry , crystallography , enantioselective synthesis , organic chemistry , catalysis , fluorescence , physics , quantum mechanics , chiral symmetry breaking , quark , nambu–jona lasinio model

International audienceThe supramolecular interactions between enantiopure TRISPHAT anion (tris(tetrachlorobenzenediolato)phosphate) and various non-chiral or pro-chiral heptamethine cyanine cations have been studied in the solid state by X-ray diffraction and in solution by NMR spectroscopy. The presence of the conformationally restricted tert-butyl functionalized cyclohexenyl moieties is responsible for the asymmetric shape interaction between the two ions revealing the chirality of the molecule. On the other hand, the strength of this interaction is controlled by the nature of the distal substituents

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