Exploring Oxidative NHC-Catalysis as Organocatalytic Polymerization Strategy towards Polyamide Oligomers |
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| Authors: | Dr. Daniele Ragno Arianna Brandolese Dr. Graziano Di Carmine Sara Buoso Giada Belletti Costanza Leonardi Prof. Olga Bortolini Prof. Monica Bertoldo Prof. Alessandro Massi |
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| Affiliation: | 1. Department of Chemical and Pharmaceutical Sciences, University of Ferrara, Via L. Borsari, 46, 44121 Ferrara, Italy;2. School of Chemical Engineering and Analytical Science, The University of Manchester, The Mill, Sackville Street, Manchester, M13 9PL UK;3. Istituto per la Sintesi Organica e la Fotoreattività, Consiglio Nazionale delle Ricerche, Via P. Gobetti, 101-40129 Bologna, Italy |
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| Abstract: | 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. |
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| Keywords: | carbenes organocatalysis oxidation polyamides polymerization |
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