Theoretical study of m-dansylaminophenylboronic acid and their species: A sugar chemosensor

m-Dansylaminophenylboronic acid is used as a fluorescent detector of fructose and other sugars. The assumed mechanism of excited state deactivation is the Photoinduced Electron Transfer (PET). The system in neutral and anionic forms (boronate anion) and their respective complexes with ethylene glycol were studied. Conformational searching was performed using AM1 semiempirical Hamiltonian and Molecular Dynamics. The most important conformations were optimized at B3LYP/6-31G∗∗ level of theory. Atoms in Molecules (AIM) theory was used to corroborate the validity of supramolecular separation. On the basis of the Kohn Sham's molecular orbitals and the UV spectra calculated at B3LYP/6-311++G(d,p) it has been found that the system can be switched off by the PET of boronate ion.