Molecular modeling techniques were employed to study the interaction of trinitrotoluene with an amplifying
fluorescent polymer used in explosive sensor devices. The pentiptycene moiety present in these
polymers appears to be the most energetically favorable binding site for trinitrotoluene. Surface features
of the polymer suggest that the small cavity feature of the pentiptycene moiety may be more available for
binding to analyte compounds due to steric crowding about the large cavity. Binding energies between
model binding sites of the polymer and various analyte compounds were more rigorously estimated by
semiempirical and ab initio techniques. Binding energies were found to be largest with trinitrotoluene
and other nitroaromatic compounds. Electrostatic and -stacking interactions between trinitrotoluene
and the model host were investigated by studying a series of modified host compounds.