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Symmetric Amphiphilic Molecules with Hydroxyl‐Cinnamic‐Acid Dimer Cores: Photo‐alterable Aggregation and Thermal Sensitivity
Author(s) -
Zhao Zhongqiang,
Xue Xiang,
Lu Jun,
Liu Huarong,
Liu Hewen
Publication year - 2017
Publication title -
journal of surfactants and detergents
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.349
H-Index - 48
eISSN - 1558-9293
pISSN - 1097-3958
DOI - 10.1007/s11743-017-1980-6
Subject(s) - micelle , chemistry , cinnamic acid , amphiphile , peg ratio , dimer , molecule , vesicle , polymer , polymer chemistry , photochemistry , organic chemistry , copolymer , chemical engineering , membrane , biochemistry , finance , aqueous solution , economics , engineering
Photolabile amphiphilic molecules with different lengths of PEG chains attached to hydroxyl cinnamic acid dimer cores (truxillic‐PEG) were synthesized. The truxillic acid core was prepared by UV‐induced dimerization of hydroxyl cinnamic acid. These symmetric truxillic‐PEG molecules formed a dispersion or stable micelles in water, which exhibited PEG chain length‐dependent thermo‐responsive behaviors, with lower critical solution temperature changing from 15 °C (PEG300 branches) to 73 °C (PEG1000 branches). Furthermore, truxillic‐PEG600 was found to form vesicles in water, whereas truxillic‐PEG300, truxillic‐PEG400 and truxillic‐PEG1000 precipitated or formed spherical micelles. If the truxillic acid cores of these truxillic‐PEG were de‐dimerized under UV illumination at 254 nm, the de‐dimerized products became more water soluble, and did not show thermal responsivity at all. The rigid truxillic ester core is very important for the formation of micelles of truxillic‐PEG capable of thermal‐responding and vesicle‐forming. Such amphiphilic polymers with a small but well‐defined hydrophobic core capable of thermal‐responding and vesicle‐forming in water could be interesting not only for academic research, but also for biological or drug application which usually demands well‐defined molecules.