Chinese Journal of Organic Chemistry >
Novel Biscalix[4]arene with Large Conjugated Aromatic Bridges: Synthesis and Complexation Properties for Dyes
Received date: 2016-02-21
Revised date: 2016-03-23
Online published: 2016-04-20
Supported by
Project supported by the National Natural Science Foundation of China (No. 21406036), the Natural Science Foundation of Fujian Province (No. 2014J01034), the Science and Technology Key Project of Fujian Province (No. 2014N0025) and the Program for Innovative Research Team in Science and Technology in Fujian Province University (No. [2012]03).
By reacting calix[4]arene-1,3-bis-amino derivative 3 with pyromellitic dianhydride, 1,4,5,8-naphthalenetetracar- boxylic dianhydride and perylene-3,4,9,10-tetracarboxylic dianhydride, respectively, three novel biscalix[4]arene derivatives 4, 5 and 6 with large conjugated aromatic bridges were prepared in “2+2” mode in yields of 60%～70%. The liquid-liquid extraction experiments of compounds 4, 5 and 6 suggested that they possess excellent extraction abilities for orange I (OI) and victoria blue B (VB). The extraction percentage of compound 6 for OI is as high as 88.3%. The complexation titration UV-vis spectra, Job plot titration and the ESI-MS complexation spectrum implied the formation of 1:1 complexes in DMSO solution. The highest association constant is 2.80×105 L·mol－1 for compound 6 with OI. The complexation abilities of compounds 4, 5 and 6 exhibit the order of compound 4< compound 5< compound 6, indicating that the aromatic conjugate bridges in biscalix[4]arene play important role for the dye complexation.
Key words： calix[4]arene; perylene; synthesis; dye; complexation
Lin Liangbin , Guo Hongyu , Yang Fafu , Yuan Jin . Novel Biscalix[4]arene with Large Conjugated Aromatic Bridges: Synthesis and Complexation Properties for Dyes[J]. Chinese Journal of Organic Chemistry, 2016 , 36(8) : 1863 -1868 . DOI: 10.6023/cjoc201602019
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