Photochemical behaviour upon the inclusion for some volatile organic compounds in new fluorescent indolizine β-cyclodextrin sensors

The potentialities of three new fluorescent indolizine modified P-cyclodextrin have been investigated as molecular chemosensors. The pyridin4-ylindolizine beta-cyclodextrin derivatives were synthesised by an amidation between the fluorescent indolizine derivatives and 6-deoxy-6-amino-beta-cyclodextrin. The multiconformational search by MM3 and AM1 method in gaseous state and in water respectively suggest the open cavity structure as the most probable. These compounds have been characterised spectroscopically by their emission spectra and their sensing ability towards 1-adamantanol, phenol and p-cresol. The fluorescent properties and sensitivity factor of the sensor containing an indolizine product with a perfluored aromatic fragment recommended it fairly as sensor for the detection of volatile organic compounds (VOCs), while the other two sensors, with an aliphatic fragment, can be utilised as biological markers. Finally, a significant bathochromic shift is observed for the sensor containing a t-butyl fragment, in such a way that this sensor may also lead to the detection of VOCs. (c) 2006 Elsevier B.V. All rights reserved.