Citation: Yi Zhu, Jingyan Zhang, Yuchao Zhang, Ying Chen, Guanghui An, Ren Liu. Designing unimolecular photoinitiator by installing NHPI esters along the TX backbone for acrylate photopolymerization and their applications in coatings and 3D printing[J]. Chinese Chemical Letters, ;2024, 35(7): 109573. doi: 10.1016/j.cclet.2024.109573 shu

Designing unimolecular photoinitiator by installing NHPI esters along the TX backbone for acrylate photopolymerization and their applications in coatings and 3D printing

Yi Zhu ^{a, b} ,
Jingyan Zhang ^b ,
Yuchao Zhang ^d ,
Ying Chen ^b ,
Guanghui An ^{c, *,} ,
Ren Liu ^{a, b, *,}

a.
Key Laboratory of Synthetic and Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122, China
b.
International Research Center for Photoresponsive Molecules and Materials, Jiangnan University, Wuxi 214122, China
c.
School of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, China
d.
Scientific Experiment Center, Hangzhou Institute of Medicine (HIM), Chinese Academy of Sciences, Hangzhou 310022, China

chemagh@163.com

liuren@jiangnan.edu.cn

Received Date: 8 November 2023
Revised Date: 19 January 2024
Accepted Date: 23 January 2024
Available Online: 29 January 2024

Figures(6)

Developing efficient and long wavelength sensitive unimolecular photoinitiators (PIs) is still facing a great challenge. In this work, a series of thioxanthone-based N-hydroxyphthalimide esters (TX-NHPIEs) were synthesized by installing NHPIEs along the TX backbone and characterized. The investigated TX-NHPIEs have a 60 nm redshift and demonstrate sterling initiating efficiency for free radical photopolymerization (FRP) under LED@450 nm light irradiation compared with the commercialized isopropylthioxanthone (ITX). Real-time ¹Hnuclear magnetic resonance (¹H NMR), electron spin resonance (ESR), decarboxylation and gas chromatograph-mass spectrometer (GC–MS) experiments and density functional theory (DFT) reveal that TX-NHPIEs can generate one alkyl radical and one N-centered iminyl radical, which can initiate FRP directly and indirectly, respectively. In other words, TX-NHPIEs absorb one photon and can generate two active radicals, which break through the limitations of common PIs. TX-NHPIE-Cpe demonstrates the highest initiating efficiency, and its application in coatings and 3D printing was also studied, indicating TX-NHPIEs have broad potential applications in photopolymerization processes.
- Photopolymerization,
- Photoinitiator,
- Energy transfer,
- Thioxanthone,
- N-Hydroxyphthalimide ester
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