Facile and Efficient Synthesis of Carbosiloxane Dendrimers via Orthogonal Click Chemistry Between Thiol and Ene. Issue 4 (16th December 2015)

• Record Type: Journal Article
• Authors: Zhang, Zhida; Feng, Shengyu; Zhang, Jie
• Is Part Of: Macromolecular rapid communications. Volume 37:Issue 4(2016)
• Page Start: 318
• Page End: 322
• Publication Date: 2015-12-16
• Subjects: carbosiloxane dendrimers -- dendrimers -- matrix‐assisted laser desorption/ionization mass spectrometry (MALDI MS) -- orthogonal click strategy -- thiol–ene chemistry; Macromolecules -- Periodicals; Polymers -- Periodicals; Chemistry -- Periodicals; 547.705
• DOI: 10.1002/marc.201500607
• Languages: English
• ISSNs: 1022-1336

Abstract

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. Abstract : Carbosiloxane dendrimers are constructed rapidly via an orthogonal click strategy combined with two sequential thiol–ene chemistries as the first example. The fifth dendrimer is obtained in a day with an excellent overall yield. A blue glow is observed when the dendrimer is exited under a UV lamp.