Solvent Switched Weak Interaction of a 4-Quinazolinone with a Cavitand Derivative

Interaction of 4-quinazolinone with tetrakis (3,5-dicarboxylatophenoxy)-cavitand derivative has been studied in methanol and dimethylformamide media using fluorescence spectroscopy and molecular modeling methods. Results show temperature dependent complex formation: either the entropy gain or the high enthalpy changes are responsible for the formation of stable complexes in two separated temperature regions. However, different thermodynamic parameters are associated to different conformations of the complexes: while the high entropy gain associated to the formation of deeply included guest in methanol, the high entropy gain is associated with the formation of weakly included guest in dimethylformamide solvent. This finding highlights the importance of dynamic properties of the species interacted in different solvents.