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Synthesis, Spectra, and Theoretical Investigations of 1,3,5-Triazines Compounds as Ultraviolet Rays Absorber Based on Time-Dependent Density Functional Calculations and three-Dimensional Quantitative Structure-Property Relationship

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Abstract

A series of 1,3,5-triazines were synthesized and their UV absorption properties were tested. The computational chemistry methods were used to construct quantitative structure-property relationship (QSPR), which was used to computer aided design of new 1,3,5-triazines ultraviolet rays absorber compounds. The experimental UV absorption data are in good agreement with those predicted data using the Time-dependent density functional theory (TD-DFT) [B3LYP/6–311 + G(d,p)]. A suitable forecasting model (R > 0.8, P < 0.0001) was revealed. Predictive three-dimensional quantitative structure-property relationship (3D-QSPR) model was established using multifit molecular alignment rule of Sybyl program, which conclusion is consistent with the TD-DFT calculation. The exceptional photostability mechanism of such ultraviolet rays absorber compounds was studied and confirmed as principally banked upon their ability to undergo excited-state deactivation via an ultrafast excited-state proton transfer (ESIPT). The intramolecular hydrogen bond (IMHB) of 1,3,5-triazines compounds is the basis for the excited state proton transfer, which was explored by IR spectroscopy, UV spectra, structural and energetic aspects of different conformers and frontier molecular orbitals analysis.

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Acknowledgements

The financial support of this work was supplied by the NSFC (NO. B020601), Scientific Research Foundation of the Education Department of Sichuan Province (NO. 12ZB128) and Key Research Fund Program (No. Z1123328) of Xihua University. The authors thank the assistant of the students of Prof. Li of College of Chemical engineering, Sichuan University for the work of computational calculations of SYBYL.

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Authors and Affiliations

  1. Key Lab of Advanced Scientific Computation of Sichuan Province, School of Science, Xihua University, Chengdu, 610039, China

    Xueding Wang, Yilian Xu, Lu Yang, Xiang Lu, Hao Zou, Weiqing Yang, Yuanyuan Zhang & Menglin Ma

  2. Key lab of Green Chemistry and Technology of Ministry of Education. Faculty of Chemistry, Sichuan University, Chengdu, 610064, China

    Yuanyuan Zhang

  3. College of Chemical Engineering, Sichuan University, Chengdu, 610065, China

    Zicheng Li

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  1. Xueding Wang
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  2. Yilian Xu
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  3. Lu Yang
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  4. Xiang Lu
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  7. Yuanyuan Zhang
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  9. Menglin Ma
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Correspondence to Menglin Ma.

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Wang, X., Xu, Y., Yang, L. et al. Synthesis, Spectra, and Theoretical Investigations of 1,3,5-Triazines Compounds as Ultraviolet Rays Absorber Based on Time-Dependent Density Functional Calculations and three-Dimensional Quantitative Structure-Property Relationship. J Fluoresc 28, 707–723 (2018). https://doi.org/10.1007/s10895-018-2235-2

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  • DOI: https://doi.org/10.1007/s10895-018-2235-2

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