Synthesis and Characterization of Azido-Substituted Ladder-like Polysilsesquioxanes and their Click Chemistry

Abstract

A novel organic-inorganic hybrid-type ladder-like poly(benzylazide) silsesquioxane (LPBAzSQ) and ladder-like poly(propylazide) silsesquioxane (LPPAzSQ) were synthesized through azidation of ladder-like poly(p-chloromethyl)phenylsilsesquioxane (LPCMPSQ) and ladder-like poly(propylchloro)silsesquioxane (LPPCSQ). The ladder-like structure of the synthesized LPBAzSQ and LPPAzSQ compounds, full substitution of azide groups, and their click chemistry with various functional groups was characterized by ¹H NMR, ¹³C NMR, ²⁹Si NMR, FT-IR, GPC. This new approach for functionalization of ladder-like silsesquioxanes has allowed for insertion of polar functional groups that have yet be examined in silsesquioxane chemistry.

Keywords:

• Polysilsesquioxanes
• ladder-like silsesquioxanes
• azidation
• click reactions
• click chemistry

Acknowledgment

This work was financially supported by a grant from the Fundamental R&D Program for Core Technology of Materials funded by the Ministry of Knowledge Economy, Republic of Korea and partially by a grant from Nano Hybrids Research Center of Korea Institute of Science and Technology (KIST).