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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Main Authors: Francesca Cicogna, Guido Giachi, Luca Rosi, Elisa Passaglia, Serena Coiai, Roberto Spiniello, Federico Prescimone, Marco Frediani
Format: Article
Language:English
Published: MDPI AG 2020-08-01
Series:Polymers
Subjects:
Online Access:https://www.mdpi.com/2073-4360/12/9/1979
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spelling 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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