Cyclodextrin-induced asymmetry of achiral nitrogen heterocycles

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Recent studies investigating the nature of fluorescence quenching effects of β-cyclodextrin (β-CDx) upon various nitrogen heterocycles suggest the importance of the position and number of nitrogen heteroatoms within the guest molecule. The sensitivity of molecules such as acridine (ACR) and phenazine (PHEN) toward the microenvironment provided by cyclodextrins appears to originate with the heteroatom. Quenching has also been observed for ACR and PHEN in the presence of α-and γ-CDx, although it is less extensive than in the β-CDx system. Induced circular dichroism (ICD) measurements are able to provide a more reliable estimate of apparent formation constants for the β-CDx systems since complex formation is a prerequisite for guest-induced symmetry in the cases discussed here. Fluorescence measurements were used to assess the association constants of the α- and γ-CDx with PHEN and ACR. The influence of size compatibility between guest and host and the orientation of the guest within the CDx molecule are also evaluated. © 1992 American Chemical Society.

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Journal of Physical Chemistry

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