光敏可逆表面活性剂4-丁基偶氮苯-4'-(乙氧基)三甲基溴化铵的合成及其光化学行为

Synthesis and Photochemical Behavior of Reversible Photosensitive Surfactant 4-Butylazobenzene-4'-( oxyethyl) trimethylammonium Bromide

以4-正丁基苯胺、1,2-二溴乙烷、苯酚为原料,通过威廉姆森成醚反应与氨基化反应合成了阳离子表面活性剂——4-丁基偶氮苯-4'-(乙氧基)-三甲基溴化铵(AZTMA),化合物结构经1HNMR进行了确证,结果表明,合成物质即为目标产物。通过紫外-可见分光光度计全波长扫描考察了AZTMA的光可逆特性,证明其能在(360±5)nm紫外光以及≥420 nm可见光光照下发生顺反异构转变。反式AZTMA溶液在紫外光的照射下达到异构平衡的时间为50 min;顺式AZTMA在可见光照射下90 min达到平衡。采用铂金板法测定了30℃下AZTMA的反式与顺式结构的临界胶束浓度(CMC)分别为2.0 mmol/L和6.0 mmol/L,结果表明,AZTMA胶束的形成与解散具备可逆调控的特性。

A photo-responsive reversible cationic surfactant 4-butylazobenzene-4＇-（ oxyethyl ） trimethylammonium bromide （ AZTMA ） was synthesized from 4-butylaniline, 1,2-ethylbromide and phenol by the methods of Williamson ether-forming reaction and amination reaction. The structure of AZTMA was characterized by means of I HNMR,and the results indicate that the obtained product was identical to its theoretical structure. The photo-reversible characteristics of AZTMA were analyzed by full wavelength scanning, and the photoisomerization occurred under the irradiation of ultraviolet light at （360 ± 5 ） nm and visible light at ≥ 420 nm. 50 rain is need for trans-AZTMA solution under the irradiation of ultraviolet light to achieve equilibrium, and 90 rain for cis-AZTMA under visible light irradiation. The critical micella concentration （CMC） values of trans-AZTMA and cis-AZTMA were detected by adopting the platinum plate method. The CMC of trans-AZTMA was 2.0 mmol/L, while that of cis-AZTMA was 6. 0 mmol/L. The results indicate that AZTMA possesses good photo-reversible characteristics and the formation and disintegration of AZTMA micelles can be reversibly controlled.