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Low‐Temperature Cu(I)‐Catalyzed “Click” Reactions for Self‐Healing Polymers
Author(s) -
Schunack Marlen,
Gragert Maria,
Döhler Diana,
Michael Philipp,
Binder Wolfgang H.
Publication year - 2012
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.201100377
Subject(s) - catalysis , polymer chemistry , polymer , solvent , chemistry , organic chemistry
Systematic investigations on the Cu(I)‐catalyzed “click” reaction between a three‐arm star polymer and low‐molecular‐weight alkynes are described. Liquid trivalent alkynes ( 2 – 7 ) are reacted either with monovalent azidotelechelic polyisobutylene 1b ( $ \overline M_{\rm n} $ = 1900 g mol −1 , PDI = 1.3) in solution, or with the trivalent azidotelechelic polyisobutylene 1a ( $ \overline M_{\rm n} $ = 4000 g mol −1 , PDI = 1.3). A significant autoacceleration is observed leading to increased reaction rates of the mono‐, di‐, and trisubstituted alkynes. Reaction in the solvent‐free state proved to be significantly faster than reaction in solution. Upon testing various Cu(I) catalysts, CuBr(PPh 3 ) 3, tripropargylamine 2 emerges as the ideal component for a room‐temperature “click” reaction with the three‐arm star polyisobutylene 1a .