Structure-properties relationship of biosourced stereocontrolled polytriazoles from click chemistry step growth polymerization of diazide and dialkyne dianhydrohexitols.
The design of dialkyne and diazide functionalized dianhydrohexitol stereoisomers (1-6) afforded a new family of starch-based polytriazoles (7-15) with defined stereochemistry through A(2) + B(2) CuAAC step growth polymerization. The present strategy gave rise to polytriazoles having a high biosourced weight fraction (superior to 60% wt) and exhibiting relatively high molar masses (M(n) = 8-17 kg/mol) that could be easily dissolved in DMF or DMSO. The obtained materials were amorphous and displayed high transition temperatures (T(g) = 125-166 °C) as well as good resistance to thermal degradation (T(d10) = 325-347 °C). Monomer stereochemistry proved to be a crucial parameter aiming at generating polymers with high T(g). Thus, optimal thermal properties were obtained with monomers having RR absolute configuration of the C-2 and C-5 carbon atoms (isomannide configuration).
Besset
Céline
C
Université de Lyon, INSA-Lyon, Université Claude Bernard Lyon 1, Ingénierie des Matériaux Polymères (UMR-CNRS 5223), Villeurbanne Cedex, France.
Pascault
Jean-Pierre
JP
Fleury
Etienne
E
Drockenmuller
Eric
E
Bernard
Julien
J
D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry*; D001386:Azides / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D055598:Chemical Phenomena; D057930:Click Chemistry / Q000379:methods; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D058105:Polymerization; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013402:Sugar Alcohols / Q000138:chemical synthesis / Q000737:chemistry*; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
D000480:Alkynes; D001386:Azides; D011108:Polymers; D013402:Sugar Alcohols; D014230:Triazoles; C543192:hexitol; D003300:Copper