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Towards a Universal Polymer Backbone: Design and Synthesis of Polymeric Scaffolds Containing Terminal Hydrogen‐Bonding Recognition Motifs at Each Repeating Unit
Author(s) -
Stubbs Ludger P.,
Weck Marcus
Publication year - 2003
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200390122
Subject(s) - romp , monomer , norbornene , polymer , polymer chemistry , hydrogen bond , polymerization , metathesis , ring opening metathesis polymerisation , materials science , alkyl , combinatorial chemistry , chemistry , molecule , organic chemistry , composite material
Abstract Polymers containing terminal hydrogen‐bonding recognition motifs based on diaminotriazine and diaminopyridine groups in their side chains for the self‐assembly of appropriate receptors have been prepared by ring‐opening metathesis polymerization (ROMP) of norbornenes. A new synthetic method for the preparation of norbornene monomers based on pure alkyl spacers is introduced. These monomers show unprecedented high reactivity using ROMP. To suppress self‐association of diaminotriazine‐based polymers, polymerizations were run in presence of N ‐butylthymine. The butylthymine acts as a protecting group via self‐assembly onto the hydrogen‐bonding sites of the polymeric scaffold, thereby solubilizing the polymer. Diaminopyridine monomers do not require the presence of a protecting group due to their low propensity to dimerize. In addition, they exhibit a high affinity for hydrogen‐bonded receptors on both monomeric and polymeric level. These polymers present our first building blocks towards the design and synthesis of a “universal polymer scaffold”.