Coumarinacyl Anilinium Salt: A Versatile Visible and NIR Photoinitiator for Cationic and Step-Growth Polymerizations,ACS Macro Letters

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Coumarinacyl Anilinium Salt: A Versatile Visible and NIR Photoinitiator for Cationic and Step-Growth Polymerizations
ACS Macro Letters ( IF 5.1 ) Pub Date : 2023-02-03 , DOI: 10.1021/acsmacrolett.2c00675
Longji Li ₁ , Mengdi Wan ₁ , Zhiquan Li _{1,

2} , Yicong Luo ₁ , Shufang Wu _{1,

3} , Xiaoxuan Liu _{1,

2} , Yusuf Yagci _{1,

4}

Affiliation

A coumarinacyl anilinium (CAA) salt, facilely synthesized via a one-pot reaction, is shown to be a versatile visible and NIR photoinitiator for cationic and step-growth polymerizations. CAA salt exhibits superior photoinitiation performance as compared to commercial iodonium salt in cationic polymerization. Upon visible-light irradiation, this salt undergoes hemolytic and heterolytic cleavage and subsequent electron transfer and hydrogen abstraction reactions, forming reactive species capable of initiating cationic polymerization of epoxides and vinyl monomers. After a short irradiation period, polymerization also proceeds in the dark due to the non-nucleophilic nature of the counteranion. NIR-induced polymerizations were successfully conducted based on upconversion photochemistry. CAA salt can also initiate step-growth polymerization of N-ethyl carbazole (NEC) by oxidation of the monomer by the photochemically formed anilium radical cations. Subsequent proton release and radical coupling reactions essentially yield polycarbazole. CAA salt, featuring straightforward synthesis and long-wavelength sensitivity as well as versatile photoinitiating performance, has great potential in various applications.

中文翻译：

香豆素酰苯胺盐：用于阳离子和逐步增长聚合的多功能可见光和近红外光引发剂

通过一锅反应轻松合成的香豆素酰苯胺 ( CAA ) 盐被证明是一种用于阳离子和逐步增长聚合的多功能可见光和 NIR 光引发剂。与阳离子聚合中的商用碘鎓盐相比，CAA盐表现出优异的光引发性能。在可见光照射下，该盐会发生溶血和异裂解以及随后的电子转移和夺氢反应，形成能够引发环氧化物和乙烯基单体阳离子聚合的活性物质。在短时间照射后，由于抗衡离子的非亲核性质，聚合也在黑暗中进行。基于上转换光化学成功地进行了 NIR 诱导的聚合。CAA盐还可以通过光化学形成的苯胺自由基阳离子氧化单体来引发N-乙基咔唑 (NEC)的逐步聚合。随后的质子释放和自由基偶联反应基本上产生聚咔唑。CAA盐具有合成简单、对长波长敏感以及多种光引发性能等特点，在各种应用中具有巨大的潜力。

更新日期：2023-02-03

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