Efficient excited‐state intramolecular proton transfer in acridone derivatives—A case study of Paratrimerin C

International Journal of Quantum Chemistry - Tập 123 Số 4 - 2023
Thi Lê Anh Nguyen1,2, Dinh Hieu Truong1,2, Thị Chinh Ngo1,2, Duy Quang Dao1,2
1Faculty of Natural Sciences, Duy Tan University, Da Nang, Vietnam
2Institute of Research and Development, Duy Tan University, Da Nang, Vietnam

Tóm tắt

AbstractParatrimerin C is a natural acridone antioxidant that is also potent as an anti‐UV agent. The photophysical process of Paratrimerin C, including the absorption and emission and the excited state intramolecular proton transfer (ESIPT) mechanism, is studied herein with time‐dependent density functional theory. The solvent effect on ESIPT is studied for polar (water) and non‐polar (benzene) solvents employing the Integral Equation Formalism Polarization Continuum Model and adding up to three explicit molecules of solvent. The normal and tautomer forms of the Paratrimerin C at the ground‐ and excited‐state structures are studied at the M06‐2X/6‐311++G(d,p) level of theory. The potential energy curves along the reaction coordinates indicate that the ESIPT is a barrier‐less reaction, and the variation of OdOa distance in the excited state shows significant molecular structure deformation along the proton transfer process following the normal‐to‐tautomerism pathway. The obtained results suggest using of acridone derivatives as efficient and tunable fluorescence molecules besides their biological activities.

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International Journal of Quantum Chemistry

Tập 123 Số 4

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