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A Simple Post‐Polymerization Modification Method for Controlling Side‐Chain Information in Digital Polymers
Author(s) -
König Niklas Felix,
Al Ouahabi Abdelaziz,
Poyer Salomé,
Charles Laurence,
Lutz JeanFrançois
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201702384
Subject(s) - side chain , polymer , azide , polystyrene , polymer chemistry , polymerization , monomer , alkyne , combinatorial chemistry , cycloaddition , chemistry , cationic polymerization , materials science , organic chemistry , catalysis
A three‐step post‐polymerization modification method was developed for the design of digitally encoded poly(phosphodiester)s with controllable side groups. Sequence‐defined precursors were synthesized, either manually on polystyrene resins or automatically on controlled pore glass supports, using two phosphoramidite monomers containing either terminal alkynes or triisopropylsilyl (TIPS) protected alkyne side groups. Afterwards, these polymers were modified by stepwise copper‐catalyzed azide–alkyne cycloaddition (CuAAC). The terminal alkynes were first reacted with a model azide compound, and after removal of the TIPS groups, the remaining alkynes were reacted with another organic azide. This simple method allows for quantitative side‐chain modification, thus opening up interesting avenues for the preparation of a wide variety of digital polymers.