title: Aggregation and pH responsive disassembly of a new acid-labile surfactant synthesized by thiol-acrylate Michael addition reaction.
abstract: Nucleophilic thiol-acrylate Michael reaction between a hydrophobic thiol and hydrophilic acrylate derivative generated a nonionic surfactant with acid-labile β-thiopropionate linker. Micellization of the surfactant, its ability to encapsulate hydrophobic dye, acid-induced disruption of the aggregate and pH-selective dye release profile have been revealed in this report. The micellar aggregates were found to be stable under neutral conditions, but they could be disrupted in acidic pH (5.3), and thus the encapsulated hydrophobic dye molecules could be selectively released. Appropriate control experiments revealed that the sulfur atom in the β-position is essential for acidic hydrolysis of the ester functionality of the surfactant.
authors.affiliation: Polymer Science Unit, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700 032, India.
authors.forename: Krishna
authors.initials: K
authors.lastname: Dan
authors.forename: Rakesh
authors.initials: R
authors.lastname: Pan
authors.forename: Suhrit
authors.initials: S
authors.lastname: Ghosh
mesh_terms: D000143:Acids / Q000737:chemistry*; D000179:Acrylates / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D008823:Micelles; D015394:Molecular Structure; D010316:Particle Size; D011721:Pyrenes / Q000737:chemistry; D013050:Spectrometry, Fluorescence; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013499:Surface Properties; D013501:Surface-Active Agents / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000143:Acids; D000179:Acrylates; D005456:Fluorescent Dyes; D008823:Micelles; D011721:Pyrenes; D013438:Sulfhydryl Compounds; D013501:Surface-Active Agents; C030984:pyrene