CRCU

Chemical Research in Chinese Universities ›› 2002, Vol. 18 ›› Issue (4): 441-444.

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Effect of Frontier Orbital on Aggregation Behavior of Barbituric Acid Derivatives

LIU Chun-ming1, YANG Wen-sheng2   

  1. 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.

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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