A cinnamic acid-type photo-cleavable surfactant

• Published in: Journal of colloid and interface science Vol. 376; no. 1; pp. 160 - 164
• Main Authors: Sakai, Hideki, Aikawa, Shohei, Matsuda, Wataru, Ohmori, Takashi, Fukukita, Yuko, Tezuka, Yoji, Matsumura, Atsutoshi, Torigoe, Kanjiro, Tsuchiya, Koji, Arimitsu, Koji, Sakamoto, Kazutami, Sakai, Kenichi, Abe, Masahiko
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier Inc 15.06.2012; Elsevier
• Subjects: Aqueous solutions; Chemistry; Cinnamates - chemistry; Cinnamic acid; Colloidal state and disperse state; Coumarin; Cyclization; Derivatives; Exact sciences and technology; General and physical chemistry; Interfacial properties; Interfacial tension; micelles; Micelles. Thin films; Photo-cleavable surfactant; Photolysis; polyethylene glycol; Polyoxyethylene; Solubilization; Surface physical chemistry; Surface Tension; Surface-Active Agents - chemistry; Surfactants; Ultraviolet Rays; Water - chemistry; Photo-cleavable surfactant; Solubilization; Cinnamic acid; Interfacial tension; Water; Interface tension; Micelle; Surfactant; Coumarin; Cyclization; Aqueous solution; Physicochemical properties; Interface
• ISSN: 0021-9797; 1095-7103
• DOI: 10.1016/j.jcis.2012.03.009

[Display omitted] ► We have developed a cinnamic acid-type photo-cleavable surfactant. ► This surfactant yields two functional materials as a result of the photo-cleavage. ► The photo-cleavage results in a significant change in interfacial properties. ► Hence, the surfactant is a photo-responsive function-exchangeable material. ► This is a new concept in stimulus-responsive amphiphilic materials. We have developed a novel cinnamic acid-type photo-cleavable surfactant. This surfactant experiences photo-cleavage through UV-induced cyclization in aqueous solutions. The photo-cleavage not only reduces its capabilities as a surfactant but also yields two functional materials including a coumarin derivative and an aminated polyoxyethylene compound. This means that the photo-cleavable surfactant synthesized in this study is a photo-responsive function-exchangeable material. In our current study, we have characterized the photo-cleavable behavior that occurs in aqueous solutions and a resulting change in interfacial properties. The photo-cleavage induces an increased interfacial tension of a squalane/water interface and a decreased solubilization capability of the surfactant micelles.