首页 | 本学科首页   官方微博 | 高级检索  
     检索      

Theoretical Study on the Electronic Structures and Spectral Properties of 1,8-Naphthalimide Derivatives
作者姓名:王艳  高慧  杨平  聂光华  宋新建
基金项目:supported by the Scientific Research Fund of Hubei Provincial Education Department(No.Q20122909);the Open Fund of Key Laboratory of Biologic Resources Protection and Utilization of Hubei Province(No.PKLHB1314);the First-class Discipline of Forestry in Hubei Minzu University
摘    要:The molecular geometries, frontier molecular orbital properties, and absorption and emission properties of three 4-phenoxy-1,8-naphthalimide derivatives, namely 4-phenoxy-N-(2-hydroxyethyl)-1,8-naphthalimide(1),4-(2-tert-butylphenoxy)-N-(2-hydroxyethyl)-1,8-naphthalimide(2), and 4-2,4-di(tert-butyl)]phenoxy-N-(2-hydroxyethyl)-1,8-naphthalimide(3), are investigated by density functional theory(DFT) and time-dependent density functional theory(TD-DFT) calculations in conjunction with polarizable continuum models(PCMs). Four functionals and ten basis sets are employed for 1 to calculate the electron transition energies, which were compared with the experimental observations. Our results reveal that the B3LYP/6-311+G(d,p) method is the best choice to reproduce the experimental spectra. Moreover, the effects of substituents on the molecular geometries, electronic structures, absorption and emission spectra are also studied at the B3LYP/6-311+G(d,p) level. We find that the gap between the highest occupied molecular orbital(HOMO) and the lowest unoccupied molecular orbital(LUMO) decreases with increasing the number of tert-butyl substituents onto the phenoxy groups, suggesting red-shift of the absorption and emission bands. This is related to the increase of conjugation from 1 to 2 and 3. Our calculations are in good agreement with the experimental results.

关 键 词:萘二甲酰亚胺  光谱性质  电子结构  胺衍生物  TD-DFT  密度泛函理论  分子轨道  B3LYP

Theoretical Study on the Electronic Structures and Spectral Properties of 1,8-Naphthalimide Derivatives
WANG Yan , GAO Hui , YANG Ping , NIE Guang-Hua , SONG Xin-Jian.Theoretical Study on the Electronic Structures and Spectral Properties of 1,8-Naphthalimide Derivatives[J].Chinese Journal of Structural Chemistry,2014,33(6):12-19.
Authors:WANG Yan  GAO Hui  YANG Ping  NIE Guang-Hua  SONG Xin-Jian
Institution:1. Key Laboratory of Biologic Resources Protection and Utilization of Hubei Province, Hubei Minzu University, Enshi 445000, China;College of Forestry and Horticultrue, Hubei Minzu University, Enshi 445000, China
2. Key Laboratory of Biologic Resources Protection and Utilization of Hubei Province, Hubei Minzu University, Enshi 445000, China
Abstract:The molecular geometries, frontier molecular orbital properties, and absorption and emission properties of three 4-phenoxy-1,8-naphthalimide derivatives, namely 4-phenoxy-N-(2-hydroxyethyl)-1,8-naphthalimide(1),4-(2-tert-butylphenoxy)-N-(2-hydroxyethyl)-1,8-naphthalimide(2), and 4-2,4-di(tert-butyl)]phenoxy-N-(2-hydroxyethyl)-1,8-naphthalimide(3), are investigated by density functional theory(DFT) and time-dependent density functional theory(TD-DFT) calculations in conjunction with polarizable continuum models(PCMs). Four functionals and ten basis sets are employed for 1 to calculate the electron transition energies, which were compared with the experimental observations. Our results reveal that the B3LYP/6-311+G(d,p) method is the best choice to reproduce the experimental spectra. Moreover, the effects of substituents on the molecular geometries, electronic structures, absorption and emission spectra are also studied at the B3LYP/6-311+G(d,p) level. We find that the gap between the highest occupied molecular orbital(HOMO) and the lowest unoccupied molecular orbital(LUMO) decreases with increasing the number of tert-butyl substituents onto the phenoxy groups, suggesting red-shift of the absorption and emission bands. This is related to the increase of conjugation from 1 to 2 and 3. Our calculations are in good agreement with the experimental results.
Keywords:-naphthalimide derivatives  density functional theory  frontier molecular orbital  absorption spectrum  emission spectrum
本文献已被 CNKI 维普 万方数据 等数据库收录!
设为首页 | 免责声明 | 关于勤云 | 加入收藏

Copyright©北京勤云科技发展有限公司  京ICP备09084417号