title: Facile and Efficient Synthesis of Carbosiloxane Dendrimers via Orthogonal Click Chemistry Between Thiol and Ene.
abstract: A combination of a thiol-Michael addition reaction and a free radical mediated thiol-ene reaction is employed as a facile and efficient approach to carbosiloxane dendrimer synthesis. For the first time, carbosiloxane dendrimers are constructed rapidly by an orthogonal click strategy without protection/deprotection procedures. The chemoselectivity of these two thiol-ene click reactions leads to a design of a new monomer containing both electron-deficient carbon-carbon double bonds and unconjugated carbon-carbon double bonds. Siloxane bonds are introduced as the linker between these two kinds of carbon-carbon double bonds. Starting from a bifunctional thiol core, the dendrimers are constructed by iterative thiol-ene click reactions under different but both mild reaction conditions. After simple purification steps the fifth dendrimer with 54 peripheral functional groups is obtained with an excellent overall yield in a single day. Furthermore, a strong blue glow is observed when the dendrimer is excited by a UV lamp.
authors.affiliation: Key Laboratory of Special Functional Aggregated Materials and Key Laboratory of Colloid and Interface Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, P. R. China.
authors.forename: Zhida
authors.initials: Z
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Special Functional Aggregated Materials and Key Laboratory of Colloid and Interface Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, P. R. China.
authors.forename: Shengyu
authors.initials: S
authors.lastname: Feng
authors.affiliation: Key Laboratory of Special Functional Aggregated Materials and Key Laboratory of Colloid and Interface Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, P. R. China.
authors.forename: Jie
authors.initials: J
authors.lastname: Zhang
mesh_terms: D057930:Click Chemistry; D050091:Dendrimers / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012833:Siloxanes / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D050091:Dendrimers; D012833:Siloxanes; D013438:Sulfhydryl Compounds
keywords: carbosiloxane dendrimers; dendrimers; matrix-assisted laser desorption/ionization mass spectrometry (MALDI MS); orthogonal click strategy; thiol-ene chemistry