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Theoretical study on excited-state intermolecular proton transfer reactions of 1H-pyrrolo[3,2-h]quinoline with water and methanol

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Abstract

The dynamics of the ultrafast excited-state multiple intermolecular proton transfer (PT) reactions in gas-phase complexes of 1H-pyrrolo[3,2-h]quinoline with water and methanol (PQ(H2O) n and PQ(MeOH) n , where n = 1, 2) is modeled using quantum-chemical simulations. The minimum energy ground-state structures of the complexes are determined. Molecular dynamics simulations in the first excited state are employed to determine reaction mechanisms and the time evolution of the PT processes. Excited-state dynamics results for all complexes reveal synchronous excited-state multiple proton transfer via solvent-assisted mechanisms along an intermolecular hydrogen-bonded network. In particular, excited-state double proton transfer is the most effective, occurring with the highest probability in the PQ(MeOH) cluster. The PT character of the reactions is suggested by nonexistence of crossings between ππ* and πσ* states.

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Acknowledgment

The authors wish to thank the Thailand Research Fund (TRF) (MRG5480294 and RTA5380010) for financial support. The computer facility at the Department of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai, Thailand, is also acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai, 50200, Thailand

    Nawee Kungwan, Rathawat Daengngern & Tammarat Piansawan

  2. Department of Chemistry, Faculty of Science, Kasetsart University, Bangkhen Campus, Bangkok, 10903, Thailand

    Supa Hannongbua

  3. Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470, Mülheim an der Ruhr, Germany

    Mario Barbatti

Authors
  1. Nawee Kungwan
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  2. Rathawat Daengngern
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  3. Tammarat Piansawan
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  4. Supa Hannongbua
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  5. Mario Barbatti
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Corresponding author

Correspondence to Nawee Kungwan.

Electronic supplementary material

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214_2013_1397_MOESM1_ESM.docx

Cartesian coordinates of ground-state optimized structures. Potential energy diagrams for selected trajectories. Time evolution of geometrical and energetic variables. (DOCX 1006 kb)

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Kungwan, N., Daengngern, R., Piansawan, T. et al. Theoretical study on excited-state intermolecular proton transfer reactions of 1H-pyrrolo[3,2-h]quinoline with water and methanol. Theor Chem Acc 132, 1397 (2013). https://doi.org/10.1007/s00214-013-1397-x

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  • DOI: https://doi.org/10.1007/s00214-013-1397-x

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