Macromolecular Dyes by Chromophore-Initiated Ring Opening Polymerization of L-Lactide
End functionalized polylactides are prepared by ring opening polymerization of L-lactide in the presence of stannous octoate (Sn(Oct)<sub>2</sub>). Three chromophores, 9H-carbazol-ethanol (CA), 9-fluorenyl-methanol (FM), and 2-(4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino)ethanol (Di...
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doaj-2056cfc499794d6e84c4a234851672772020-11-25T03:37:48ZengMDPI AGPolymers2073-43602020-08-01121979197910.3390/polym12091979Macromolecular Dyes by Chromophore-Initiated Ring Opening Polymerization of L-LactideFrancesca Cicogna0Guido Giachi1Luca Rosi2Elisa Passaglia3Serena Coiai4Roberto Spiniello5Federico Prescimone6Marco Frediani7Consiglio Nazionale delle Ricerche Istituto di Chimica dei Composti OrganoMetallici, Sede Secondaria di Pisa (CNR ICCOM-SS-Pisa), 56124 Pisa, ItalyDipartimento di Chimica “U. Schiff” Università degli Studi di Firenze, 50019 Sesto Fiorentino, ItalyDipartimento di Chimica “U. Schiff” Università degli Studi di Firenze, 50019 Sesto Fiorentino, ItalyConsiglio Nazionale delle Ricerche Istituto di Chimica dei Composti OrganoMetallici, Sede Secondaria di Pisa (CNR ICCOM-SS-Pisa), 56124 Pisa, ItalyConsiglio Nazionale delle Ricerche Istituto di Chimica dei Composti OrganoMetallici, Sede Secondaria di Pisa (CNR ICCOM-SS-Pisa), 56124 Pisa, ItalyConsiglio Nazionale delle Ricerche Istituto di Chimica dei Composti OrganoMetallici, Sede Secondaria di Pisa (CNR ICCOM-SS-Pisa), 56124 Pisa, ItalyDipartimento di Chimica e Chimica Industriale Università di Pisa, 56126 Pisa, ItalyDipartimento di Chimica “U. Schiff” Università degli Studi di Firenze, 50019 Sesto Fiorentino, ItalyEnd functionalized polylactides are prepared by ring opening polymerization of L-lactide in the presence of stannous octoate (Sn(Oct)<sub>2</sub>). Three chromophores, 9H-carbazol-ethanol (CA), 9-fluorenyl-methanol (FM), and 2-(4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino)ethanol (Disperse Red 13, DR), are for the first time used as co-initiators in the polymerization process. The polymerization reaction is initiated by conventional thermal treatment, but in the case of FM, microwave-assisted polymerization is also carried out. CA and FM absorb and emit in the UV portion of the electromagnetic spectrum, whereas DR absorbs in the visible part. The obtained end-capped polylactides derivatives show the same photophysical properties as the initiator, so they are “macromolecular dyes” (MDs) that can be used “as synthesized” or can be blended with commercial poly(lactic acid) (PLA). The blends of PLA with MDs have ultraviolet-visible (UV-Vis) absorption and fluorescence emission features similar to that of MDs and thermal properties typical of PLA. Finally, migration tests, carried out onto the blends of PLA with MDs and PLA with free chromophores, show that MDs are less released than free chromophores both in solution and in the solid phase.https://www.mdpi.com/2073-4360/12/9/1979ring opening polymerization of L-lactide (RPO)chromophores end-capped PLAdyed PLAphotophysical propertiesmigration testsmicrowave-assisted polymerization |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Francesca Cicogna Guido Giachi Luca Rosi Elisa Passaglia Serena Coiai Roberto Spiniello Federico Prescimone Marco Frediani |
spellingShingle |
Francesca Cicogna Guido Giachi Luca Rosi Elisa Passaglia Serena Coiai Roberto Spiniello Federico Prescimone Marco Frediani Macromolecular Dyes by Chromophore-Initiated Ring Opening Polymerization of L-Lactide Polymers ring opening polymerization of L-lactide (RPO) chromophores end-capped PLA dyed PLA photophysical properties migration tests microwave-assisted polymerization |
author_facet |
Francesca Cicogna Guido Giachi Luca Rosi Elisa Passaglia Serena Coiai Roberto Spiniello Federico Prescimone Marco Frediani |
author_sort |
Francesca Cicogna |
title |
Macromolecular Dyes by Chromophore-Initiated Ring Opening Polymerization of L-Lactide |
title_short |
Macromolecular Dyes by Chromophore-Initiated Ring Opening Polymerization of L-Lactide |
title_full |
Macromolecular Dyes by Chromophore-Initiated Ring Opening Polymerization of L-Lactide |
title_fullStr |
Macromolecular Dyes by Chromophore-Initiated Ring Opening Polymerization of L-Lactide |
title_full_unstemmed |
Macromolecular Dyes by Chromophore-Initiated Ring Opening Polymerization of L-Lactide |
title_sort |
macromolecular dyes by chromophore-initiated ring opening polymerization of l-lactide |
publisher |
MDPI AG |
series |
Polymers |
issn |
2073-4360 |
publishDate |
2020-08-01 |
description |
End functionalized polylactides are prepared by ring opening polymerization of L-lactide in the presence of stannous octoate (Sn(Oct)<sub>2</sub>). Three chromophores, 9H-carbazol-ethanol (CA), 9-fluorenyl-methanol (FM), and 2-(4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino)ethanol (Disperse Red 13, DR), are for the first time used as co-initiators in the polymerization process. The polymerization reaction is initiated by conventional thermal treatment, but in the case of FM, microwave-assisted polymerization is also carried out. CA and FM absorb and emit in the UV portion of the electromagnetic spectrum, whereas DR absorbs in the visible part. The obtained end-capped polylactides derivatives show the same photophysical properties as the initiator, so they are “macromolecular dyes” (MDs) that can be used “as synthesized” or can be blended with commercial poly(lactic acid) (PLA). The blends of PLA with MDs have ultraviolet-visible (UV-Vis) absorption and fluorescence emission features similar to that of MDs and thermal properties typical of PLA. Finally, migration tests, carried out onto the blends of PLA with MDs and PLA with free chromophores, show that MDs are less released than free chromophores both in solution and in the solid phase. |
topic |
ring opening polymerization of L-lactide (RPO) chromophores end-capped PLA dyed PLA photophysical properties migration tests microwave-assisted polymerization |
url |
https://www.mdpi.com/2073-4360/12/9/1979 |
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