苯骈唑类化合物电子光谱及其构效关系研究
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摘要
应用量子化学中的密度泛函理论(DFT)和含时密度泛函理论(TD-DFT)对一系列苯骈唑类化合物的键长,键角,电荷分布和前线分子轨道(HOMO和LUMO)能量,电子吸收光谱进行了计算。
首先,先由Chem3D程序包获得溴代苯丙烯基苯骈噁唑分子的初始构型,接着在不施加任何对称性限制的条件下,在RHF(Restricted Hartree-Fock)水平上,采用半经验PM3方法对分子进行几何构型预优化。在此基础上,用5种方法B3LYP/3-21G、B3LYP/6-31G、B3LYP/6-31G~*、B3LYP/6-31G~(**)和HF/6-31G~*对分子进行了全优化并把计算结果与实验值进行了比较,得到的结果显示B3LYP/6-31G~*方法计算苯骈唑类化合物耗时较少,结果良好。
然后采用所确定的最佳计算方法B3LYP/6-31G~*研究了苯骈噁唑类化合物芳环单溴取代物,芳环上氟、氯、溴、硝基、甲基和甲氧基等取代化合物以及共轭体系化合物,探讨了不同取代基对苯骈噁唑类化合物的几何构型、电子结构和电子光谱等的影响。对发射波长实验值与分子基态能隙△ε以及单电子第一激发能△E还有偶极矩μ进行线性拟合,并得出了回归方程,预测结果与实验值符合的很好。
本文还研究了苯乙烯基苯骈噁唑,苯乙烯基苯骈噻唑,苯乙烯基苯骈咪唑的几何构型,电子结构,电子光谱,最小振动频率和振动强度等。
最后,计算了一系列苯骈唑类化合物,激发波长实验值与分子基态能隙△ε以及单电子第一激发能△E还有偶极矩μ成线性关系,并得出了回归方程,预测结果与实验值极为接近。
In this thesis,a relatively high level theoretical investigation has been performed using the density functional theory and time-dependent density functional theory methods to calculate the bond length,bond angles,charge distribution and frontier orbital energy, electronic spectra of a sort of benzoxazole compounds(including the benzoxazole compounds,the benzimidazole compounds and the benzothiazole compounds).
First,the structures of monobromo substituted 2-propenylbenzoxazole compound have been carried out on Chem3D and then are opted by PM3 of semi-empirical methods at the level of RHF(Restricted Hartree-Fock)without any restrict of symmetry.On the base,five methods of B3LYP/3-21G,B3LYP/6-31 G,B3L YP/6-31G~*,B3LYP/6-31G~(**)and HF/6-31G~* are used to optimize the structures and compared with the experimental results,the results show that the method of B3LYP/6-31 G~* spent fewer time and got better data.
Then,monobromo substituted benzoxazole compounds and substituted benzoxazole compounds with F,Cl,Br,NO_2,CH_3,OCH_3,N(CH_3)_2 and compounds of conjugated strctures have been studied at the B3LYP/6-31G~* level of density functional theory.The curve of the experimental fluorescent wavelengths and the state energy gap△ε,single electronic excited energy△E and dipole moment is linear.Regression equation is also got,and the predicted result is near to the experimental result.
In addition,the geometry structures,electronic structures,the electronic spectrum,the intensity and the frequency of the benzoxazole compounds have been calculated and discussed.
Finally,we discuss a sort of benzoxazole compounds.The curve of the experimental excited wavelengths and the state energy gap△ε,single electronic excited energy△E and dipole moment is linear.Regression equation is also got,and the predicted result is near to the experimental result.
首先,先由Chem3D程序包获得溴代苯丙烯基苯骈噁唑分子的初始构型,接着在不施加任何对称性限制的条件下,在RHF(Restricted Hartree-Fock)水平上,采用半经验PM3方法对分子进行几何构型预优化。在此基础上,用5种方法B3LYP/3-21G、B3LYP/6-31G、B3LYP/6-31G~*、B3LYP/6-31G~(**)和HF/6-31G~*对分子进行了全优化并把计算结果与实验值进行了比较,得到的结果显示B3LYP/6-31G~*方法计算苯骈唑类化合物耗时较少,结果良好。
然后采用所确定的最佳计算方法B3LYP/6-31G~*研究了苯骈噁唑类化合物芳环单溴取代物,芳环上氟、氯、溴、硝基、甲基和甲氧基等取代化合物以及共轭体系化合物,探讨了不同取代基对苯骈噁唑类化合物的几何构型、电子结构和电子光谱等的影响。对发射波长实验值与分子基态能隙△ε以及单电子第一激发能△E还有偶极矩μ进行线性拟合,并得出了回归方程,预测结果与实验值符合的很好。
本文还研究了苯乙烯基苯骈噁唑,苯乙烯基苯骈噻唑,苯乙烯基苯骈咪唑的几何构型,电子结构,电子光谱,最小振动频率和振动强度等。
最后,计算了一系列苯骈唑类化合物,激发波长实验值与分子基态能隙△ε以及单电子第一激发能△E还有偶极矩μ成线性关系,并得出了回归方程,预测结果与实验值极为接近。
In this thesis,a relatively high level theoretical investigation has been performed using the density functional theory and time-dependent density functional theory methods to calculate the bond length,bond angles,charge distribution and frontier orbital energy, electronic spectra of a sort of benzoxazole compounds(including the benzoxazole compounds,the benzimidazole compounds and the benzothiazole compounds).
First,the structures of monobromo substituted 2-propenylbenzoxazole compound have been carried out on Chem3D and then are opted by PM3 of semi-empirical methods at the level of RHF(Restricted Hartree-Fock)without any restrict of symmetry.On the base,five methods of B3LYP/3-21G,B3LYP/6-31 G,B3L YP/6-31G~*,B3LYP/6-31G~(**)and HF/6-31G~* are used to optimize the structures and compared with the experimental results,the results show that the method of B3LYP/6-31 G~* spent fewer time and got better data.
Then,monobromo substituted benzoxazole compounds and substituted benzoxazole compounds with F,Cl,Br,NO_2,CH_3,OCH_3,N(CH_3)_2 and compounds of conjugated strctures have been studied at the B3LYP/6-31G~* level of density functional theory.The curve of the experimental fluorescent wavelengths and the state energy gap△ε,single electronic excited energy△E and dipole moment is linear.Regression equation is also got,and the predicted result is near to the experimental result.
In addition,the geometry structures,electronic structures,the electronic spectrum,the intensity and the frequency of the benzoxazole compounds have been calculated and discussed.
Finally,we discuss a sort of benzoxazole compounds.The curve of the experimental excited wavelengths and the state energy gap△ε,single electronic excited energy△E and dipole moment is linear.Regression equation is also got,and the predicted result is near to the experimental result.
引文
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[19]廖显威,苏宇.“双”吡唑啉类化合物的荧光光谱理论研究.光谱学和光谱分析,2004,24(8):966-969
[20]钱一鸣,王莹.水溶液种四种杂环化合物的荧光光谱理论研究.光谱学和光谱分析,2004,24(9):1079-1081
[21]王传明,卑凤利,杨绪杰.2-苯基苯并咪唑衍生物非线性光学性质的从头算研究.分子科学学报,2004,20(2):36-40
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