Citation: ZHAO Pu-Su, JING Long, LI Yu-Feng, ZHU Yuan, WANG Jing, JIAN Fang-Fang. Comparative Studies on Two 1,8-Naphthalimide Derivatives with Experimental and Theoretical Methods[J]. Chinese Journal of Structural Chemistry, ;2014, 33(5): 676-686. shu

Comparative Studies on Two 1,8-Naphthalimide Derivatives with Experimental and Theoretical Methods

ZHAO Pu-Su ^a,b,, ,
JING Long ^a ,
LI Yu-Feng ^a ,
ZHU Yuan ^a ,
WANG Jing ^a ,
JIAN Fang-Fang ^a

a.
a. New Materials & Function Coordination Chemistry Laboratory, Qingdao University of Science and Technology, Qingdao, Shandong 266042, China;
b.
b. Jiangsu Key Laboratory for Chemistry of Low-dimensional Materials, Huaiyin Normal University, Huaian, Jiangsu 223300, China

Corresponding author: ZHAO Pu-Su,
Received Date: 28 October 2013
Available Online: 9 December 2013
Fund Project: Natural Science Foundation of Shandong Province (ZR2009AL020) (No. BS2010CL021)

Two 1,8-naphthalimide derivatives of 7H-benzimidazo[2,1,-a]benz[de] isoquinolin-7-one (1) and 4-bromo-7H-benzimidazo[2,1,-a]benz[de]isoquinolin-7-one (2) have been synthesized and characterized by elemental analysis, IR, ¹H NMR, UV-Vis and fluorescence spectra. For the two compounds, density functional theory (DFT) calculations of the structures and natural population atomic charge analysis have been performed at the B3LYP/6-311G** level of theory. Based on Onsager reaction filed model and by using TD-DFT method at the B3LYP/6-311G** level, electron spectra of 1 and 2 with solvent effect in CHCl₃ solvent have been predicted, which are in agreement with the experimental ones. Comparative studies on 1 and 2 indicate that introducing an electron-withdrawing group of Br into the 4-position of naphthalene ring in 2 does not significantly make the molecular geometry of 2 different from that of 1, but evidently changes the atomic charge redistribution, moves the positive-negative charges center and then changes the dipole moment in 2. Additionally, for compound 2, the existence of Br atom has also influenced the peak intensity and peak locations in both electron and fluorescence spectra.
- 1,8-naphthalimids,
- DFT calculation,
- atomic charge distribution,
- electronic spectra,
- fluorescence spectra
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