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Citation: GONG Lin-Bo, GONG Shu-Ling, DONG Hai-Qing, ZHANG Chun-Lei, CHEN Yuan-Yin. Fluorescence Property and Liquid Crystalline Behavior of Calix[4] arene Containing Azobenzene Photochromic Group[J]. Chinese Journal of Applied Chemistry, ;2006, 23(9): 1023-1026. shu

Fluorescence Property and Liquid Crystalline Behavior of Calix[4] arene Containing Azobenzene Photochromic Group

1.
School of Chemistry and Molecular Science, Wuhan University, Wuhan 430072

Corresponding author: GONG Shu-Ling,
Received Date: 19 October 2005
Available Online: 26 February 2006

The reaction of 4'-hydroxy-4-methyl azobenzene(1) and 1,6-dibromohexane afforded 6-bromo-1-((4-((4-methylphenyl)azo)phenyl)oxy)hexane(2),which was further reacted with p-tert-butylcalix[4] arene to give calix[4] arene derivative(3), whose lower rim was modified by azobenzene photochromic group.The structure of compound 3 was characterized by ¹H NMR and ESI-MS.The fluorescence intensity of compound 3 is 2~4 times higher than that of compounds 1 and 2 as the azobenzene group concentration was in the range of 8.0×10^-5 to 8.0×10^-4 mol/L,indicating that the fluorescence quantum yield of azobenzene group can be improved by attaching it to the calix[4] arene skeleton.The liquid crystalline behavior of compound 3 was studied by POM and DSC.Compound 3 exhibited enhanced texture of smectic liquid crystal from 209.4℃ to 219.5℃ on heating,while compound 2 exhibited liquid crystalline phase from 87.4 to 84.2℃ on cooling.It was found that the calix[4] arene skeleton can fix the conformation of the azobenzene photochromic group and help the formation of liquid crystalline morphology.
- azobenzene,
- calixarene,
- thermotropic liquid crystal,
- fluorescence
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