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Theoretical explorations about the excited state behaviors for two novel high efficient ESIPT compounds

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Abstract

Two high efficient excited state intramolecular proton transfer (ESIPT) compounds (i.e., 3-(5-([1,1′-biphenyl]-4-yl)oxazol-2-yl)-4′-(N,N-diphenylamino)-[1,1′-biphenyl]-4-ol (1) and 4′-(N,N-diphenylamino)-3-(5-(4′-(diphenylamino)-[1,1′-biphenyl]-4-yl)oxazol-2-yl)-5-methyl-[1,1′-biphenyl]-4-ol (2)) are explored theoretically. Based on DFT and time-dependent DFT (TDDFT) methods, we investigate the hydrogen bonding interactions and ESIPT mechanism. Via B3LYP/TZVP/IEFPCM (toluene) theoretical level, we reappear the experimental steady-state spectra, which demonstrate that the theoretical manner is reasonable and effective. Based on reduced density gradient (RDG) versus sign(λ2)ρ analyses, we confirm intramolecular hydrogen bond for both 1-enol and 2-enol. Investigating geometrical parameters and infrared (IR) vibrational spectra, we verify the O-H···N should be strengthened in the S1 state for 1-enol and 2-enol systems. Exploring frontier molecular orbitals (MOs) and charge density difference (CDD) maps, we find charge redistribution provides the tendency of ESIPT. The constructed potential energy curves demonstrate that the proton transfer should happen in the S1 state. Particularly, the low potential energy barriers of forward and backward ESIPT process for both 1 and 2 systems, the dynamical equilibrium could be verified, which means 1 and 2 systems should be potential for novel white light LEDs materials. This work not only explores and explains previous experimental phenomenon, but also makes a reasonable assignment about the ESIPT mechanism.

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Funding

This work was supported by the National Natural Science Foundation of China (grant no. 11404112), the Key Scientific Research Project of Colleges and Universities of Henan Province of China (18A140023, 16B140002), and Science and Technology Research Project of Henan Province (172102210391).

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Authors and Affiliations

  1. School of Mathematics and Statics, North China University of Water Resources and Electric Power, Zhengzhou, 450046, China

    Yusheng Wang, Qiaoli Zhang, Xiaoyan Song & Dapeng Yang

  2. Basic Teaching Department, Jiaozuo University, Jiaozuo, 454000, China

    Guang Yang

  3. State Key Laboratory of Molecular Reaction Dynamics, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, China

    Dapeng Yang

Authors
  1. Yusheng Wang
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  2. Guang Yang
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  3. Qiaoli Zhang
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  4. Xiaoyan Song
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  5. Dapeng Yang
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Correspondence to Dapeng Yang.

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Wang, Y., Yang, G., Zhang, Q. et al. Theoretical explorations about the excited state behaviors for two novel high efficient ESIPT compounds. Struct Chem 29, 1817–1823 (2018). https://doi.org/10.1007/s11224-018-1165-6

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  • DOI: https://doi.org/10.1007/s11224-018-1165-6

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