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

Daniele Ragno; Arianna Brandolese; Graziano Di Carmine; Sara Buoso; Giada Belletti; Costanza Leonardi; Olga Bortolini; Monica Bertoldo; Alessandro Massi

doi:10.1002/chem.202004296

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

Daniele Ragno
, Arianna Brandolese
, Graziano Di Carmine
, Sara Buoso
, Giada Belletti
, Costanza Leonardi
, Olga Bortolini
, Monica Bertoldo
, Alessandro Massi^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

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 (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.

Original language	English
Pages (from-to)	1839-1848
Number of pages	10
Journal	Chemistry - A European Journal
Volume	27
Issue number	5
Early online date	28 Sept 2020
DOIs	https://doi.org/10.1002/chem.202004296
Publication status	Published - 21 Jan 2021

Bibliographical note

Publisher Copyright:
© 2020 Wiley-VCH GmbH

Keywords

carbenes
organocatalysis
oxidation
polyamides
polymerization

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.202004296

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@article{e8ba6d887524451ba2bba61e8407e799,

title = "Exploring Oxidative NHC-Catalysis as Organocatalytic Polymerization Strategy towards Polyamide Oligomers",

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{\textquoteright}-[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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author = "Daniele Ragno and Arianna Brandolese and \{Di Carmine\}, Graziano and Sara Buoso and Giada Belletti and Costanza Leonardi and Olga Bortolini and Monica Bertoldo and Alessandro Massi",

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year = "2021",

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AU - Ragno, Daniele

AU - Brandolese, Arianna

AU - Di Carmine, Graziano

AU - Buoso, Sara

AU - Belletti, Giada

AU - Leonardi, Costanza

AU - Bortolini, Olga

AU - Bertoldo, Monica

AU - Massi, Alessandro

PY - 2021/1/21

Y1 - 2021/1/21

N2 - 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.

AB - 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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KW - organocatalysis

KW - oxidation

KW - polyamides

KW - polymerization

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DO - 10.1002/chem.202004296

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AN - SCOPUS:85097819790

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JO - Chemistry - A European Journal

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IS - 5

ER -

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

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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