| 光谱学与光谱分析 |
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| Molecular Geometries and Theoretical Electronic Spectra of Four 1,8-Naphthyridine Derivatives |
| CHI Shao-ming1, 2, 3, LI Li1, 2, CHEN Yong1, FU Wen-fu1, 2* |
1. Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, China
2. Graduate University of Chinese Academy of Sciences, Beijing 100049, China
3. College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650092, China |
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Abstract The molecular geometries of four 2,4-dimethyl-7-amino-1,8-naphthyridine derivatives were optimized with B3LYP/6-31G(d) method. The energies of their frontier molecular orbitals and the molecular structures were investigated theoretically. The theoretical electronic spectra were calculated with TD-DFT in gas phase, PCM-TD-B3LYP/6-31+G(d) and semiempirical ZINDO in CH2Cl2 solution. The influences of solvent model and calculation methods on the electronic absorption spectra were also probed. The calculated results show that delocalized π bonds exist in the four 1,8-naphthyridine derivatives, and their energy gaps (ΔE) between HOMO and LUMO are relatively small. The variation in their ΔE values gives a consistent trend with that of their electronic absorption with λmax. Theoretical spectra achieved prove that their absorptions are red-shifted when the delocalization of π electrons is enhanced or the capability to donate electron by a substituted group is increased. The maximum absorption peaks of the four derivatives originate from π(HOMO)→π*(LUMO) transition. The spectra calculated at the PCM-B3LYP/6-31+G(d) level have little difference from experimental results: the differences in wavelength are 2.6, 10.3, 5.3 and 6.9 nm, whereas those in energies are 0.03, 0.09, 0.04 and 0.08 eV, respectively. The obtained results suggest that electronic spectra calculated by TD-DFT on the bases of geometries optimized with B3LYP/6-31(d) are in agreement with experimental ones, and can account for the different spectroscopic properties of the four 1,8-naphthyridine derivatives.
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Received: 2009-03-23
Accepted: 2009-06-26
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Corresponding Authors:
FU Wen-fu
E-mail: fuwf@mail.ipc.ac.cn
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