Issue 12, 2022

Bio-based porphyrins pyropheophorbide a and its Zn-complex as visible-light photosensitizers for free-radical photopolymerization

Abstract

A chlorophyll a derivative, namely pyropheophorbide a (Pyro), and the corresponding zinc(II) complex (Zn-Pyro) were used for the first time as visible-light photosensitizers (PS) for free-radical photopolymerization (FRP) when combined with an iodonium salt derivative (Iod) and different amines. The reaction mechanisms involving Pyro and Zn-Pyro coupled with Iod and/or MDEA were deeply investigated using steady-state photolysis, fluorescence experiments, laser-flash photolysis (LFP), and electron-paramagnetic resonance spin trapping (EPR-ST) methods. According to the remarkable absorption properties of Pyro and Zn-Pyro, FRP could occur under blue-light (LED@405 nm and LED@455 nm), and under red-light (LED@625 nm and LED@660 nm) irradiation. Conversions of up to 80% of PEG-diacrylate were obtained using two-component (PS/Iod and PS/amine) or three-component (PS/Iod/amine) photoinitiating systems. Several amines used as co-initiators were compared, and N-methyl-diethanolamine (MDEA) and the bio-based thiol-amine cysteamine (Cys) exhibited very interesting kinetic results. Notably, the performances in FRP obtained with the Zn-Pyro/Iod/Cys system constitute a promising step in the development of a fully bio-based photoinitiating system.

Graphical abstract: Bio-based porphyrins pyropheophorbide a and its Zn-complex as visible-light photosensitizers for free-radical photopolymerization

Supplementary files

Article information

Article type
Paper
Submitted
28 Dis 2021
Accepted
06 Feb 2022
First published
07 Feb 2022

Polym. Chem., 2022,13, 1658-1671

Bio-based porphyrins pyropheophorbide a and its Zn-complex as visible-light photosensitizers for free-radical photopolymerization

L. Breloy, V. Brezová, S. Richeter, S. Clément, J. Malval, S. Abbad Andaloussi and D. Versace, Polym. Chem., 2022, 13, 1658 DOI: 10.1039/D1PY01714D

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements