Effect of Frontier Orbital on Aggregation Behavior of Barbituric Acid Derivatives

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Two amphiphilic barbituric acid derivatives with a D-π-A structure, 5-(4-dodecyloxybenzylidene)-(1H,3H)-2,4,6-pyrimidinetrione(PB_ 12) and 5-(4-N,N-didodecylaminobenzylidene)-(1H,3H)-2,4,6-pyrimidintrione(AB_ 12) were found to show different aggregation behavior in chloroform. PB_ 12, a derivative with weak electron donating and strong electron drawing substituents, tends to aggregate in a head-to-tail manner, whereas AB_ 12, 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 AB_ 12 and PB_ 12 show that their energy levels of LUMO approach each other, however, the energy level of HOMO of AB_ 12 is much higher than that of PB_ 12. Two amphiphilic barbituric acid derivatives with a D-π-A structure of 5- (4-dodecyloxybenzylidene) - (1H, 3H) -2,4,6-pyrimidinetrione (PB_12) and 5- ) - (1H, 3H) -2,4,6-pyrimidintrione (AB_12) were found to show different aggregation behavior in chloroform. PB_12, a derivative with weak electron donating and strong electron drawing substituents, tends to aggregate in a head -to-tail manner, but AB_12, 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 AB_12 and PB_12 show that their energy levels of LUMO approach each other, however, the energy level of HOMO of AB 12 is much higher than that of PB 12.
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