Towards a universal polymer backbone: design and synthesis of polymeric scaffolds containing terminal hydrogen-bonding recognition motifs at each repeating unit.
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".
Stubbs
Ludger P
LP
School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, GA 30332-0400, USA.
Weck
Marcus
M
D055598:Chemical Phenomena; D002627:Chemistry, Physical; D006860:Hydrogen Bonding; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009636:Norbornanes / Q000737:chemistry; D011108:Polymers / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry; D014227:Triazines / Q000737:chemistry
D007202:Indicators and Reagents; D009636:Norbornanes; D011108:Polymers; D011725:Pyridines; D014227:Triazines