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Exploring Oxidative NHC‐Catalysis as Organocatalytic Polymerization Strategy towards Polyamide Oligomers
Author(s) -
Ragno Daniele,
Brandolese Arianna,
Di Carmine Graziano,
Buoso Sara,
Belletti Giada,
Leonardi Costanza,
Bortolini Olga,
Bertoldo Monica,
Massi Alessandro
Publication year - 2021
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.202004296
Subject(s) - monomer , condensation polymer , polyamide , catalysis , polymer chemistry , carbene , polymerization , methylene , chemistry , organic chemistry , polymer
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 ( M n ) 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, M n = 62.8 kg mol −1 ; poly(decamethylene 2,5‐furandicarboxylamide, PA10F, M n = 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.