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Theoretical investigation on the spectroscopic properties of furylfulgide with different substituents and design of novel bis ‐furylfulgimide photochromes
Author(s) -
Liu XianHe,
Zhao ZengXia,
Zhang Wei,
Yin TingTing,
Zhang HongXing
Publication year - 2017
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.25327
Subject(s) - bathochromic shift , chemistry , density functional theory , steric effects , time dependent density functional theory , molecular orbital , absorption (acoustics) , excited state , computational chemistry , absorption spectroscopy , polar effect , monomer , molecule , toluene , photochemistry , stereochemistry , materials science , organic chemistry , atomic physics , polymer , physics , quantum mechanics , composite material , fluorescence
Density functional theory and time‐dependent density functional theory were employed to theoretically analyze the effect of different substituents on the spectroscopic properties of furylfulgide. The result shows that the absorption spectra of ring‐closed isomer which substituted by an electron‐donating group (NH 2 ) at the R 3 ‐position of furylfulgide has an evident bathochromic shift compared with the others. Due to the steric hindrance effect, the difference of absorption wavelength was evidently enlarged by introducing several representative electron‐withdrawing groups at the R 6 ‐position of furylfulgide. In addition, we also designed a series of novel dimers which combined two furylfulgimide monomers into one new molecule. The relevant frontier molecular orbitals, energy levels and absorption properties were analyzed in detail by the calculation of low‐lying excited states. Finally, taking BFF‐6 ( bis ‐furylfulgimide) for an example, we discussed the transformation mechanism of four stable isomers in the toluene solution. Our conclusions manifest that the asymmetrical BFF‐6 can act as a potential multifunctional molecular switch in consideration of its distinguishable absorption bands and reversible conversion process. We hope that this research will be beneficial to design more practical and efficient molecular switch for further applications.