Quantum chemical simulation of the interaction of membrane fluorescent probe 4-dimethylaminochalcone with hydroxy groups of the environment

• Published in: Russian chemical bulletin 2013-05, Vol.62 (5), p.1143-1155
• Main Authors: Sakovich, R. A., Polyak, B. M., Gularyan, S. K., Romanov, A. N., Svetlichnyi, V. Yu, Sarkisov, O. M.
• Format: Article
• Language: English
• Subjects: Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Full Articles; Inorganic Chemistry; Organic Chemistry
• ISSN: 1066-5285; 1573-9171
• DOI: 10.1007/s11172-013-0157-3

The quantum chemical simulation of the ground and electron-excited states of diverse complexes of fluorescent probe 4-dimethylaminochalcone (DMAC) and water in vacuo was performed by the HF/MP2 and RI-CC2 methods. Molecules of the DMAC probe and water can form five types of stable complexes. The geometries corresponding to the potential energy minimum and dipole moments for two lowest singlet and one lowest triplet states were calculated for each type of the complexes. The partial charges on the DMAC atoms and their changes due to the intramolecular charge transfer upon photoexcitation were determined. The coordination of the water molecule at the carbonyl group of DMAC is preferable in vacuo . The formation of hydrogen bonds between the carbonyl group of DMAC and water molecules decreases the energy of the excited state of the complex 1 (π, π*), due to which the fluorescence yield increases upon photoexcitation. The calculation results are confirmed by the experimental data on studying the fluorescence of the probe in binary mixtures of benzene and alcohols.