Synthesis of γ-cyclodextrin substituted bis(acyl)phosphane oxide derivative (BAPO-γ-CyD) serving as multiple photoinitiator and crosslinking agent

Andrea Cosola; Riccardo Conti; Vijay Kumar Rana; Marco Sangermano; Annalisa Chiappone; Joëlle Levalois-Grützmacher; Hansjörg Grützmacher

doi:10.1039/D0CC01732A

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Synthesis of γ-cyclodextrin substituted bis(acyl)phosphane oxide derivative (BAPO-γ-CyD) serving as multiple photoinitiator and crosslinking agent†

Andrea Cosola,

^a Riccardo Conti,

^b Vijay Kumar Rana,^bc Marco Sangermano,

^a Annalisa Chiappone,

^a Joëlle Levalois-Grützmacher^bd and Hansjörg Grützmacher

*^b

Author affiliations

* Corresponding authors

^a DISAT, Politecnico di Torino, Corso Duca degli Abruzzi 21, 10129 Torino, Italy

^b Department of Chemistry and Applied Biosciences, ETH Zurich, 8093 Zurich, Switzerland
E-mail: hgruetzmacher@ethz.ch

^c Department of Chemistry, Melville Laboratory for Polymer Synthesis, University of Cambridge, Cambridge CB2 1EW, UK

^d Université des Antilles, FWI, 97110 Guadeloupe, France

Abstract

A new multi-photoactive γ-cyclodextrin substituted bis(acyl)phosphane oxide derivative (BAPO-γ-CyD) was successfully prepared via a convergent synthesis using a phospha-Michael-addition, as confirmed by ¹H-, ¹³C-, ³¹P-NMR and IR spectroscopy and mass spectrometry. Kinetic studies carried out by photo-DSC and photo-rheology demonstrated its outstanding efficiency as a photoinitiator for free-radical polymerization. Remarkably, it is found that BAPO-γ-CyD also acts as a crosslinking agent to convert monofunctional methacrylate monomers into self-standing thermosetting networks with extensive swelling capability in water.

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Article information

DOI: https://doi.org/10.1039/D0CC01732A
Article type: Communication
Submitted: 06 Mar 2020
Accepted: 24 Mar 2020
First published: 25 Mar 2020
This article is Open Access

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Chem. Commun., 2020,56, 4828-4831

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Synthesis of γ-cyclodextrin substituted bis(acyl)phosphane oxide derivative (BAPO-γ-CyD) serving as multiple photoinitiator and crosslinking agent

A. Cosola, R. Conti, V. K. Rana, M. Sangermano, A. Chiappone, J. Levalois-Grützmacher and H. Grützmacher, Chem. Commun., 2020, 56, 4828 DOI: 10.1039/D0CC01732A

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Chemical Communications

Synthesis of γ-cyclodextrin substituted bis(acyl)phosphane oxide derivative (BAPO-γ-CyD) serving as multiple photoinitiator and crosslinking agent†

Abstract

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Synthesis of γ-cyclodextrin substituted bis(acyl)phosphane oxide derivative (BAPO-γ-CyD) serving as multiple photoinitiator and crosslinking agent

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