nitrophenols and sebacic-acid

The bis(p-nitrophenyl) esters of succinic acid, adipic acid and sebacic acid have been synthesized, respectively, by employing 1,3-dicyclohexylcarbodiimide (DCC) as a dehydration agent. The composition and structure of the esters have been characterized by elemental analysis, FTIR, 1H NMR and DSC. Furthermore, the host-guest interactions of the esters with beta-cyclodextrin (beta-CD) have been studied systematically by using fluorescence quenching, fluorescence spectroscopy and UV-Vis spectroscopy measurements. It was demonstrated that the chain of the esters was longer, the interactions was weaker between the esters and the beta-CD. Both p-nitrophenyl groups in bis(p-nitrophenyl) esters of succinic acid can enter the inner cavity of beta-CD. In contrast, only one of the groups in bis(p-nitrophenyl) esters of adipic acid can enter the cavity. For bis(p-nitrophenyl) esters of sebacic acid, however, both groups can not enter the cavity of the beta-CD. The difference in the host-guest interactions of the three esters with beta-CD has been attributed to the difference in the conformations adopted by the esters. Based upon these observations, it is proposed that the esters with short linker may be more suitable for construction of new networks, which are based upon, in concept, host-guest interactions.

Topics: Adipates; beta-Cyclodextrins; Decanoic Acids; Dicarboxylic Acids; Dicyclohexylcarbodiimide; Esters; Magnetic Resonance Spectroscopy; Nitrophenols; Spectrometry, Fluorescence; Spectrophotometry, Ultraviolet; Spectroscopy, Fourier Transform Infrared; Spectrum Analysis; Succinates