Issue 33, 2022

Naphthoquinone-based imidazolyl esters as blue-light-sensitive Type I photoinitiators

Abstract

In this work, a series of Type I photoinitiators (PIs), based on the naphthoquinone scaffold, were designed and synthesized for the first time in order to induce photopolymerization under visible light. As a result, these PIs exhibit excellent photoinitiation abilities in the presence of acrylate monomers upon LED@405 or @455 nm irradiation. Interestingly, some compounds have better photoinitiation performance than the benchmark Type I phosphine-oxide, i.e. diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (TPO) upon exposure to LED@455 nm. Chemical mechanisms supporting the photopolymerization process were investigated through different techniques as well as theoretical calculations. In addition, the newly proposed structures were also investigated in two-component photoinitiating systems and exhibited a higher efficiency in free radical photopolymerization. Finally, a direct laser writing approach was successfully used to fabricate 3D objects.

Graphical abstract: Naphthoquinone-based imidazolyl esters as blue-light-sensitive Type I photoinitiators

Supplementary files

Article information

Article type
Paper
Submitted
13 Jun 2022
Accepted
29 Jul 2022
First published
01 Aug 2022

Polym. Chem., 2022,13, 4817-4831

Naphthoquinone-based imidazolyl esters as blue-light-sensitive Type I photoinitiators

F. Hammoud, A. Pavlou, A. Petropoulos, B. Graff, M. G. Siskos, A. Hijazi, F. Morlet-Savary, F. Dumur and J. Lalevée, Polym. Chem., 2022, 13, 4817 DOI: 10.1039/D2PY00753C

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