title: Monocatenary, branched, double-headed, and bolaform surface active carbohydrate esters via photochemical thiol-ene/-yne reactions.
abstract: An original and versatile method for the synthesis of a range of novel mannose-based surfactants was developed via metal-free photo-induced thiol-ene/-yne 'click' reactions. This light-mediated hydrothiolation reaction involving a thiolated mannose was successfully applied to terminal and internal alkenes, dienes, and alkynes, leading to monocatenary, branched, double-headed, and bolaform amphiphilic carbohydrate esters, respectively. A surface activity study showed that these new compounds possess valuable properties and display specific behavior at the air-water interface. It also demonstrated the greater flexibility of the thioether moiety in the spacer of the surfactants produced via a thiol-ene reaction in comparison with the triazole heterocyclic rings in similar glucose-based surfactants synthesized elsewhere by the alkyne-azide 1,3-dipolar addition.
authors.affiliation: Center for Education and Research on Macromolecules (CERM), University of Liege, Chemistry Department, Sart-Tilman, Allée de la Chimie 3, Bat B6a, B-4000 Liege, Belgium.
authors.forename: Cédric
authors.initials: C
authors.lastname: Boyère
authors.forename: Guy
authors.initials: G
authors.lastname: Broze
authors.forename: Christophe
authors.initials: C
authors.lastname: Blecker
authors.forename: Christine
authors.initials: C
authors.lastname: Jérôme
authors.forename: Antoine
authors.initials: A
authors.lastname: Debuigne
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry*; D057930:Click Chemistry; D004952:Esters; D057927:Hydrophobic and Hydrophilic Interactions; D055668:Photochemical Processes; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013499:Surface Properties; D013501:Surface-Active Agents / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000475:Alkenes; D000480:Alkynes; D002241:Carbohydrates; D004952:Esters; D013438:Sulfhydryl Compounds; D013501:Surface-Active Agents
keywords: Bolaform; Click chemistry; Glycosurfactants; Photochemistry; Thiol-ene/-yne