Acta Phys. -Chim. Sin. ›› 2009, Vol. 25 ›› Issue (06): 1143-1148.doi: 10.3866/PKU.WHXB20090616

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Structures and UV-Vis Absorption Spectra of 1,8-Naphthalimide Derivatives

QI Qi, SUN Yue-Ming, HA Yong-Quan   

  1. School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, P. R. China
  • Received:2009-01-19 Revised:2009-02-25 Published:2009-06-05
  • Contact: SUN Yue-Ming E-mail:sun@seu.edu.cn

Abstract:

Ground state geometries of a series of 1, 8-naphthalimide derivatives were calculated by density functional theory (DFT). Their UV-Vis absorption spectra in gaseous, C6H12 (cyclohexane) and CH2Cl2 environments were calculated by the time dependent-DFT (TDDFT) method and the conductor polarizable continuummodel-TDDFT (CPCM-TDDFT) method. We found that theoretical values were in good agreement with X-ray geometric parameters. The addition of various substituents (H, methyl, phenyl, and naphthyl) to the 4 and 5 positions of the naphthalic ring's amines lengthened the (N—C) bond length between the amine and the naphthalimide moiety. This bond lengthening resulted in more intramolecular charge transfer and a lower energy gap. Both the bathochromic effect and the frontier orbital electron cloud density showed that the absorption maximum corresponds to a π-π* transition. By comparison to the maximumabsorption peak of UV-Vis absorption spectrumof the B isomer, that of the A isomer was red shifted and this was mainly attributed to more intramolecular charge transfer and a lower energy gap.

Key words: 1,8-Naphthalimides derivative, Density function theory, Absorption spectrum

MSC2000: 

  • O641