2,4,6-Trimethylbenzoyldiphenylphosphine oxide (TPO) analog: a non-cytotoxic type-I photoinitiator for free radical photopolymerization†

IF 9.3 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Green Chemistry Pub Date : 2025-01-07 DOI:10.1039/d4gc04127e

Jiansong Yin , Yijun Zhang , Bernadette Graff , Céline Dietlin , Michael Schmitt , Fabrice Morlet-Savary , Tatiana Petithory , Laurent Pieuchot , Jing Zhang , Yangyang Xu , Jean-Michel Becht , Jacques Lalevée , Pu Xiao

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引用次数: 0

Abstract

2,4,6-Trimethylbenzoyldiphenylphosphine oxide (TPO) is a highly efficient and widely used photoinitiator, but it is currently facing significant concerns regarding cytotoxicity. This work investigates a type-I photoinitiator designed as a safer alternative to TPO. In particular, a TPO analog was synthesized, namely 6-(2,4,6-trimethylbenzoyl)-(6H)-dibenz[c,e][1,2]oxaphosphorin 6-oxide (TDOPO), incorporating 9,10-dihydro-9-oxa-10-phosphaphenanthrene 10-oxide (DOPO) motif. This compound presents promising characteristics as a type I photoinitiator. It can be synthesized efficiently in just two steps under mild conditions with a reduced environmental impact using commercially available chemicals, without need for extensive purification procedures. Notably, TDOPO exhibits absorption close to the visible spectrum, suggesting its potential for use in visible light curing applications. Comparative studies reveal that TDOPO exhibits strong photoinitiation ability for the free radical photopolymerization of acrylate in both thin and thick samples. The photochemical mechanism studies indicate its capability to generate three distinct types of free radicals: the 2,4,6-trimethylbenzoyl, an oxygen-centered and a phosphorus-centered free radical. In addition, TDOPO shows no cytotoxicity in a 20-hour assay, a result far superior to that of TPO. These findings underscore the potential of TDOPO as an effective and safer alternative to TPO in photopolymerization processes.

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来源期刊

Green Chemistry 化学-化学综合

CiteScore

16.10

自引率

7.10%

发文量

677

审稿时长

1.4 months

期刊介绍： Green Chemistry is a journal that provides a unique forum for the publication of innovative research on the development of alternative green and sustainable technologies. The scope of Green Chemistry is based on the definition proposed by Anastas and Warner (Green Chemistry: Theory and Practice, P T Anastas and J C Warner, Oxford University Press, Oxford, 1998), which defines green chemistry as the utilisation of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products. Green Chemistry aims to reduce the environmental impact of the chemical enterprise by developing a technology base that is inherently non-toxic to living things and the environment. The journal welcomes submissions on all aspects of research relating to this endeavor and publishes original and significant cutting-edge research that is likely to be of wide general appeal. For a work to be published, it must present a significant advance in green chemistry, including a comparison with existing methods and a demonstration of advantages over those methods.