Effect of Frontier Orbital on Aggregation Behavior of Barbituric Acid Derivatives

高等学校化学研究 ›› 2002, Vol. 18 ›› Issue (4): 441-444.

Effect of Frontier Orbital on Aggregation Behavior of Barbituric Acid Derivatives

LIU Chun-ming¹, YANG Wen-sheng²

1. Department of Chemistry, Changchun Teachers' Colleage, Changchun 130023, P. R. China;
2. College of Chemistry, Jilin University, Changchun 130023, P. R. China

收稿日期:2002-03-10 出版日期:2002-12-24 发布日期:2011-08-04
基金资助:
Supported by the National Natural Science Foundation of China(No.50172019) and Excellent Young Teachers Program of MOE, P. R. China.

Effect of Frontier Orbital on Aggregation Behavior of Barbituric Acid Derivatives

LIU Chun-ming¹, YANG Wen-sheng²

1. Department of Chemistry, Changchun Teachers' Colleage, Changchun 130023, P. R. China;
2. College of Chemistry, Jilin University, Changchun 130023, P. R. China

Received:2002-03-10 Online:2002-12-24 Published:2011-08-04
Supported by:
Supported by the National Natural Science Foundation of China(No.50172019) and Excellent Young Teachers Program of MOE, P. R. China.

摘要/Abstract

摘要： Two amphiphilic barbituric acid derivatives with a D-π-A structure, 5-(4-dodecyloxybenzylidene)-(1H,3H)-2,4,6-pyrimidinetrione(PB₁₂) and 5-(4-N,N-didodecylaminobenzylidene)-(1H,3H)-2,4,6-pyrimidintrione(AB₁₂) were found to show different aggregation behavior in chloroform. PB₁₂, a derivative with weak electron donating and strong electron drawing substituents, tends to aggregate in a head-to-tail manner, whereas AB₁₂, a derivative with both strong electron donating and drawing substituents, tends to aggregate in a face-to-face manner at a higher concentration. The cyclic voltammograms of AB₁₂ and PB₁₂ show that their energy levels of LUMO approach each other, however, the energy level of HOMO of AB₁₂ is much higher than that of PB₁₂.

关键词: Barbituric acid derivative, Aggregation, HOMO, LUMO

Abstract: Two amphiphilic barbituric acid derivatives with a D-π-A structure, 5-(4-dodecyloxybenzylidene)-(1H,3H)-2,4,6-pyrimidinetrione(PB₁₂) and 5-(4-N,N-didodecylaminobenzylidene)-(1H,3H)-2,4,6-pyrimidintrione(AB₁₂) were found to show different aggregation behavior in chloroform. PB₁₂, a derivative with weak electron donating and strong electron drawing substituents, tends to aggregate in a head-to-tail manner, whereas AB₁₂, a derivative with both strong electron donating and drawing substituents, tends to aggregate in a face-to-face manner at a higher concentration. The cyclic voltammograms of AB₁₂ and PB₁₂ show that their energy levels of LUMO approach each other, however, the energy level of HOMO of AB₁₂ is much higher than that of PB₁₂.

Key words: Barbituric acid derivative, Aggregation, HOMO, LUMO

LIU Chun-ming, YANG Wen-sheng. Effect of Frontier Orbital on Aggregation Behavior of Barbituric Acid Derivatives[J]. 高等学校化学研究, 2002, 18(4): 441-444.

LIU Chun-ming, YANG Wen-sheng. Effect of Frontier Orbital on Aggregation Behavior of Barbituric Acid Derivatives[J]. Chemical Research in Chinese Universities, 2002, 18(4): 441-444.

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Effect of Frontier Orbital on Aggregation Behavior of Barbituric Acid Derivatives

Effect of Frontier Orbital on Aggregation Behavior of Barbituric Acid Derivatives

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