A Density Functional Theory Study of Indigo and Its Derivatives

Acta Chimica Sinica ›› 2004, Vol. 62 ›› Issue (10): 963-968. Previous Articles Next Articles

靛蓝及其取代物的密度泛函理论研究

薛运生¹, 贡雪东¹, 肖鹤鸣¹, 田禾²

1. 南京理工大学化工学院, 南京, 210094;
2. 华东理工大学精细化工研究所, 上海, 200237

投稿日期:2003-08-14 修回日期:2004-01-30 发布日期:2014-02-17
通讯作者: 肖鹤鸣,E-mail:xiao@mail.njust.edu.cn E-mail:xiao@mail.njust.edu.cn
基金资助:
国家自然科学基金(No.29836150)资助项目.

A Density Functional Theory Study of Indigo and Its Derivatives

XUE Yun-Sheng¹, GONG Xue-Dong¹, XIAO He-Ming¹, TIAN He²

1. School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094;
2. Institute of Fine Chemical, East China University of Science and Technology, Shanghai 200237

Received:2003-08-14 Revised:2004-01-30 Published:2014-02-17

Abstract

Indigo is one of the oldest known natural dyes. In the past decades, indigoids have been extensively investigated by experimental and theoretical methods. In theoretical study, semiempirical or Hartree-Fock MO methods were mostly used. Indigo and its 4,4'-, 5,5'-, 6,6'-, and 7,7'-disubstituted derivatives with F, Cl, Br, NO₂, CH₃O, and CH₃ groups have been studied at the B3LYP/6-31G^* level of density functional theory (DFT) in this paper. The substitution effects of the electron donating and electron accepting groups at various positions on the geometry structures, electronic structures, and the electronic spectra have been investigated, and quite good results were achieved compared with the experimental results. The electronic spectra have been calculated using the time dependent density functional theory (TD-DFT) approach. The calculated results showed that the first singlet excited state of indigoids resulted from the electron transition from the highest occupied MO (HOMO) to the lowest unoccupied MO (LUMO).

Key words: indigo, density functional theory(DFT), time-dependent density functional theory(TD-DFT), substitution effect, electronic spectra

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XUE Yun-Sheng, GONG Xue-Dong, XIAO He-Ming, TIAN He. A Density Functional Theory Study of Indigo and Its Derivatives[J]. Acta Chimica Sinica, 2004, 62(10): 963-968.

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靛蓝及其取代物的密度泛函理论研究

A Density Functional Theory Study of Indigo and Its Derivatives

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