Electronic substituent effects on ketocoumarin-based photoinitiators: Structure-activity relationships for high-efficiency LED photopolymerization

IF 6.5 2区材料科学 Q1 CHEMISTRY, APPLIED

Progress in Organic Coatings Pub Date : 2025-03-17 DOI:10.1016/j.porgcoat.2025.109229

Shuheng Fan , Xun Sun , Haipeng Liu , Xue Qi , Jingjing Lou , Peike Wang , Yulian Pang , Yingquan Zou , Jun Wei

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引用次数: 0

Abstract

Ketocoumarins have emerged as promising candidates for efficient Norrish type II photoinitiators (PIs) due to their long light absorption wavelengths, excellent photosensitive activity, and high photoinduced electron transfer efficiency. In this study, a series of ketocoumarin-based PIs (KCs) were designed and synthesized with various substituents, including methyl, trifluoromethyl, hydroxyl, phenyl, p-methylaminophenyl, and p-methylthiophenyl, linked to carbonyl. The primary objective was to explore the structure-reactivity-efficiency relationships of KCs, which are crucial for LED photopolymerization. The introduction of electron-withdrawing groups linked to carbonyl resulted in a relative redshift in absorption and enhanced photoinitiation efficiency in KCs. In contrast, the incorporation of electron-donating groups led to a blueshift in absorption or significant changes due to alterations in the chromophore's functional structure. These effects were confirmed through theoretical calculations. Notably, S-KC-F, with carbonyl connected to trifluoromethyl, exhibited superior photoinitiation performance, surpassing that of commercial PIs KC-01 and ITX under UV-LED irradiation. Additionally, S-KC-F exhibited good solubility, suggesting its potential for practical applications; however, its poor cytocompatibility may restrict its use in food packaging and biomedicine. These findings provide a strategic approach to designing high-performance PIs.

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来源期刊

Progress in Organic Coatings 工程技术-材料科学：膜

CiteScore

11.40

自引率

15.20%

发文量

577

审稿时长

48 days

期刊介绍： The aim of this international journal is to analyse and publicise the progress and current state of knowledge in the field of organic coatings and related materials. The Editors and the Editorial Board members will solicit both review and research papers from academic and industrial scientists who are actively engaged in research and development or, in the case of review papers, have extensive experience in the subject to be reviewed. Unsolicited manuscripts will be accepted if they meet the journal''s requirements. The journal publishes papers dealing with such subjects as: • Chemical, physical and technological properties of organic coatings and related materials • Problems and methods of preparation, manufacture and application of these materials • Performance, testing and analysis.