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The effect of molecular structure on intramolecular charge-transfer in 1, 3, 4-oxadiazole derivatives

Meng, Lingyan et al.

Journal of photochemistry and photobiology A. Volume 377: (2019, May 15th); pp 309-317

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  • Title:
    The effect of molecular structure on intramolecular charge-transfer in 1, 3, 4-oxadiazole derivatives
  • Author: Meng, Lingyan;
    Chen, Fangyi;
    Bai, Fu-Quan;
    Bai, Binglian;
    Wang, Haitao;
    Li, Min
  • Found In: Journal of photochemistry and photobiology A. Volume 377: (2019, May 15th); pp 309-317
  • Journal Title: Journal of photochemistry and photobiology A
  • Subjects: Intramolecular charge transfer--1, 3, 4-oxadiazole--Symmetry-breaking--Fluorescence; Dewey: 541.35
  • Rights: Licensed
  • Abstract: Graphical abstract Highlights Three new methoxyphenyl substituted 1, 3, 4-oxadiazole derivatives are designed. Theoretical and experimental study on the effect of molecular structure on ICT character. Octupolar molecule shows stronger ICT character than other two counterparts. Abstract In order to study the effect of molecular structure on intramolecular charge transfer character, we designed and synthesized three methoxyphenyl substituted 1, 3, 4-oxadiazole derivatives, where the D-A branches are attached to the core benzene ring in different ways. The photophysical properties of these three molecules were systematically investigated by means of experimental and theoretical studies. Different degrees of fluorescence red-shift in polar solvents were observed in these compounds. Both 1, 4-substituted L-OXD and 1, 3-substituted B-OXD exhibit a 30˜40 nm red-shift in the fluorescence spectra during the increase of solvent polarity, while 1, 3, 5-substituted T-OXD exhibits more obvious solvatochromic behavior (>100 nm) than L-OXD and B-OXD, points to a large increase in the dipole moment of the excited state of T-OXD with solvent polarity. Furthermore, theoretical analysis on the electron density map and ADCH charge indicated that the electron is transferred from side methoxyphenyl units to 1, 3, 4-oxadiazole ring and center benzene ring, and more transferred charge could be observed in T-OXD. These results reflect that constructing octupolar molecular structures could be an effective way to influence the ICT character.
  • Identifier: System Number: ETOCvdc_100081894891.0x000001; Journal ISSN: 1010-6030; 10.1016/j.jphotochem.2019.04.011
  • Publication Date: 2019
  • Physical Description: Electronic
  • Shelfmark(s): 5034.840000
  • UIN: ETOCvdc_100081894891.0x000001

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