Royal College of Surgeons in Ireland
Polymers 2019-11-01808.pdf (5.53 MB)
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Crosslinking of electrospun fibres from unsaturated polyesters by bis-triazolinediones (TAD)

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journal contribution
posted on 2021-04-09, 15:29 authored by Viviane Chiaradia, Saltuk B Hanay, Scott D Kimmins, Débora de Oliveira, Pedro HH Araújo, Claudia Sayer, Andreas HeiseAndreas Heise
Crosslinking of an unsaturated aliphatic polyester poly(globalide) (PGl) by bistriazolinediones (bisTADs) is reported. First, a monofunctional model compound, phenyl-TAD (PTAD), was tested for PGl functionalisation. 1H-NMR showed that PTAD-ene reaction was highly efficient with conversions up to 97%. Subsequently, hexamethylene bisTAD (HM-bisTAD) and methylene diphenyl bisTAD (MDP-bisTAD) were used to crosslink electrospun PGl fibres via one- and two-step approaches. In the one-step approach, PGl fibres were collected in a bisTAD solution for in situ crosslinking, which resulted in incomplete crosslinking. In the two-step approach, a light crosslinking of fibres was first achieved in a PGl non-solvent. Subsequent incubation in a fibre swelling bisTAD solution resulted in fully amorphous crosslinked fibres. SEM analysis revealed that the fibres' morphology was uncompromised by the crosslinking. A significant increase of tensile strength from 0.3 ± 0.08 MPa to 2.7 ± 0.8 MPa and 3.9 ± 0.5 MPa was observed when PGI fibres were crosslinked by HM-bisTAD and MDP-bisTAD, respectively. The reported methodology allows the design of electrospun fibres from biocompatible polyesters and the modulation of their mechanical and thermal properties. It also opens future opportunities for drug delivery applications by selected drug loading.


Science Foundation Ireland (SFI), grant number 13/IA/1840

Science Foundation Ireland, grant number 07/IN1/B1792

CAPES (Coordenação de Aperfeiçoamento de Pessoal de Nível Superior) PDSE 2016, grant number 88881.135318/2016-01

CNPq (Conselho Nacional de Desenvolvimento Científico e Tecnológico)



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Published Citation

Chiaradia V, Hanay SB, Kimmins SD, de Oliveira D, Araújo PHH, Sayer C, Heise A. Crosslinking of electrospun fibres from unsaturated polyesters by bis-triazolinediones (TAD). Polymers (Basel). 2019;11(11):1808.

Publication Date

4 November 2019

PubMed ID



  • Chemistry

Research Area

  • Chemistry and Pharmaceutical Sciences
  • Biomaterials and Regenerative Medicine




  • Published Version (Version of Record)