Exploring Oxidative NHC‐Catalysis as Organocatalytic Polymerization Strategy towards Polyamide Oligomers

The polycondensation of diamines and dialdehydes promoted by an N‐heterocyclic carbene (NHC) catalyst in the presence of a quinone oxidant and hexafluoro‐2‐propanol (HFIP) is herein presented for the synthesis of oligomeric polyamides (PAs), which are obtained with a number‐average molecular weight...

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Bibliographic Details
Published in:Chemistry : a European journal 2021-01, Vol.27 (5), p.1839-1848
Main Authors: Ragno, Daniele, Brandolese, Arianna, Di Carmine, Graziano, Buoso, Sara, Belletti, Giada, Leonardi, Costanza, Bortolini, Olga, Bertoldo, Monica, Massi, Alessandro
Format: Article
Language:English
Subjects:
carbenes
Catalysis
Catalysts
Chemical synthesis
Chemistry
Condensation polymerization
Diamines
Molecular weight
Monomers
NMR
Nuclear magnetic resonance
Oligomers
organocatalysis
Oxidants
oxidation
Oxidizing agents
Polyamide resins
Polyamides
polymerization
Propanol
Quinones
Thermal properties
Thermodynamic properties
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Summary:The polycondensation of diamines and dialdehydes promoted by an N‐heterocyclic carbene (NHC) catalyst in the presence of a quinone oxidant and hexafluoro‐2‐propanol (HFIP) is herein presented for the synthesis of oligomeric polyamides (PAs), which are obtained with a number‐average molecular weight (Mn) in the range of 1.7–3.6 kg mol−1 as determined by NMR analysis. In particular, the utilization of furanic dialdehyde monomers (2,5‐diformylfuran, DFF; 5,5’‐[oxybis(methylene)]bis[2‐furaldehyde], OBFA) to access known and previously unreported biobased PAs is illustrated. The synthesis of higher molecular weight PAs (poly(decamethylene terephthalamide, PA10T, Mn = 62.8 kg mol−1; poly(decamethylene 2,5‐furandicarboxylamide, PA10F, Mn = 6.5 kg mol−1) by a two‐step polycondensation approach is also described. The thermal properties (TGA and DSC analyses) of the synthesized PAs are reported. Organocatalytic step‐growth polymerization: fossil‐ and biobased polyamides are obtained under mild ambient conditions by polycondensation of diamines and dialdehydes promoted by an N‐heterocyclic carbene in the presence of recyclable external oxidant and nucleophilic additive.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202004296