Novel 1,2-3,4-Bridged and 1,3-Bridged Calix[4]arene Based on Large s-triazine Conjugate Systems: Synthesis and Complexation for Dyes

作者:Bai, Xiaoyan; Yang, Fafu*; Xie, Jianwei; Guo, Hongyu
来源:Journal of Macromolecular Science, Part A: Pure and Applied Chemistry , 2013, 50(3): 334-339.
DOI:10.1080/10601325.2013.755884

摘要

Two novel 1,2-3,4-bridged and 1,3-bridged calix[4]arenes 6 and 9 based on large s-triazine conjugate systems were designed and synthesized in high yields. The liquid-liquid extraction experiment showed that they possessed excellent extraction abilities towards one cationic and three anionic dyes [Orange I (OI), Methylene blue (MB), Neutral red (NR), Brilliant green (BG)]. The highest extraction percentage of compound 9 was 91.2% for BG. The complexation UV-Vis spectra of compounds 6 and 9 with four dyes indicated the existence of complexation action between hosts and guests with 1:1 ratio of complexation in DMSO solution. The association constants suggested that the 1,2-3,4-bridging structure was more favorable for producing excellent complexation abilities than 1,3-bridging structure. The association constant of compound 9 with BG was as high as 4.5 x 10(6) M-1.

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