Abstract
In this work, eleven heteroleptic copper complexes were designed and studied as photoinitiators of polymerization in three-component photoinitiating systems in combination with an iodonium salt and an amine. Notably, ten of them exhibited panchromatic behavior and could be used for long wavelengths. Ferrocene-free copper complexes were capable of efficiently initiating both the radical and cationic polymerizations and exhibited similar performances to that of the benchmark G1 system. Formation of acrylate/epoxy IPNs was also successfully performed even upon irradiation at 455 nm or at 530 nm. Interestingly, all copper complexes containing the 1,1′-bis(diphenylphosphino)ferrocene ligand were not photoluminescent, evidencing that ferrocene could efficiently quench the photoluminescence properties of copper complexes. Besides, these ferrocene-based complexes were capable of efficiently initiating free radical polymerization processes. The ferrocene moiety introduced in the different copper complexes affected neither their panchromatic behaviors nor their abilities to initiate free radical polymerizations.
Highlights
Photopolymerization or polymerization initiated through light exposure is a process widely used industrially
All photoinitiators were prepared with analyti(c1a00l MpuHrzit).yTuhep1Htochaecmceipcatlesdhisfttsawnderaerdresfefroenrcendewto tohregsaonlviecnct opmeapksoDunMdSsO((>29.489%p)p;mth),is was cheCcDkeCdl3b(7y.2h6ipgphmfi)ealnddNthMe R13Cancahleymsicsa. l2s,h9i-fDtsipwhereenryelf-e1r,e1n0c-epdhteontahnetshorlvoelinntepe[2a0k]D, 2M,9S-Odibutyl1,1(04-9p.5hpenpman),thCrDoCliln3e(7[72.01]p,p2m-t)e.rAt-lbl uphtyolt-o1in,1it0i-aptohresnwaenrethprroelpianreed[2w2i]thanandalcyotmicapl lpeuxriGty1u[p3] were syntothaecsciezpetdedasstapnrdeavridosufsolrynreewpoorrgteandicincotmhepoliutnedrast(u>r9e8,%w);itthhiosuwtams cohdeicfkiecdatbioynhiagnhdfieinldsimilar yieNldMs.R analysis. 2,9-Diphenyl-1,10-phenanthroline [20], 2,9-dibutyl-1,10-phenanthroline [21], 2-tert-butyl-1,10-phenanthroline [22] and complex G1 [3] were synthesized as previously
Copper Complexes Structures Inspired by Copper Complex G1
Summary
Photopolymerization or polymerization initiated through light exposure is a process widely used industrially. Various applications such as adhesives, dentistry [1], medicine, coatings [2], composites [3], laser writing and 3D printing [4] are already based on this process. A major drawback of industrial applications of photopolymerization is the use of UV light which is a source of safety concerns [5]. A copper complex named G1 (Scheme 1) was developed as a highly efficient photoinitiator for free radical and cationic polymerization under visible LED irradiation [3,11,12,13]. Considering the efficiency of the photocatalyst G1, other copper complexes, with similar behavior, are still developed with the aim of concomitantly initiating both radical and cationic polymerizations
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