Journal
CHEMPHYSCHEM
Volume 21, Issue 5, Pages 442-449Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cphc.201901095
Keywords
cucurbituril; photochemistry; self-assembly; stereoisomers; styryl dye
Funding
- Russian Science Foundation [19-73-20187]
- Russian Science Foundation [19-73-20187] Funding Source: Russian Science Foundation
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The photochemical isomerization of a styrylpyridinium dye (SP) bearing an unsymmetrically attached benzo-15-crown-5 ether has been studied in aqueous solution in the absence and presence of cucurbit[7]uril (CB[7]). The detailed analysis of the UV/Vis and NMR spectra showes that the isomeric composition of the photostationary mixtures of SP can be modulated by the host-guest complexation with CB[7]. It was found that steric hindrance caused by encapsulation of SP in the host cavity induces the exclusive formation of the anti conformer of Z-SP in contrast with the mixture of both anti and syn conformers obtained during photoisomerization of the dye without CB[7]. Remarkably, the displacement of anti Z-SP from CB[7] does not lead to the transformation of the anti Z-isomer into the syn Z-isomer pointing out the conformational memory of the system. The results provide an interesting example of the supramolecular stereorecognition by the achiral CB[7] host.
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