A benzophenone-naphthalimide derivative (BPND) bearing tertiary amine groups has been developed as a high-performance photoinitiator in combination with 2,4,6-tris(trichloromethyl)-1,3,5-triazine or an iodonium salt for both the tree radical polymerization (FRP) of acrylates and the cationic
polymerization (CP) of epoxides upon exposure to near UV and visible LEDs (385–470 nm). BPND can even produce radicals without any added hydrogen donor. The photochemical mechanisms are studied by molecular orbital calculations, steady state photolysis, electron spin resonance spin trapping, fluorescence, cyclic voltammetry and laser flash photolysis techniques. These novel BPND based photoinitiating systems exhibit an
efficiency higher than that of the well-known camphorquinone- based systems (FRP and CP) or comparable to that of bis(2,4,6-trimethylbenzoyl)-phenylphosphineoxide (FRP at 455 nm).

A benzophenone-naphthalimide derivative as versatile photoinitiator of polymerization under near UV and visible lights

Deprotonation of the radical cations of aromatic amines, such as anilines, generally occurs much more slowly than other fragmentation reactions. Here we report a stereoelectronic effect involving twisting of the anilino group out of the plane of the benzene ring that results in a significantly increased rate of reactivity toward deprotonation. Quantitative studies of the rate constants for deprotonation as a function of aniline radical cation pKa (Bronsted plots) demonstrate that the effect is not simply due to a change in the reaction thermodynamics. By combining this stereoelectronic effect with covalent attachment of carboxylate as a base, aniline radical cations that undergo unimolecular deprotonation with rate constants as high as 108 s-1, even in unfavorable protic media, are described.

Efficient unimolecular deprotonation of aniline radical cations

Photoinitiators for Free Radical Polymerization Reactions

Photo-initiated cross-linking of multifunctional acrylic esters in polymeric binders was investigated based on digital imaging using the Computer-to-Plate (CtP) technology applying laser exposure in the near-infrared (NIR). Generation of initiating radicals occurs by electron transfer from the excited state of the NIR-sensitizer to the radical generator, an onium salt. Iodonium salts derived from several borates and those with the bis(trifluoromethylsulfonyl)imide anion resulted in lithographic materials with high sensitivity. Photo-induced electron transfer plays a major function to generate initiating radicals by a sensitized mechanism but thermal events also influence sensitivity of the coating. Internal conversion was the major deactivation pathway while a certain fraction of NIR-dye fluorescence was also available. A line shape focused laser system with emission in the NIR was successfully used to bake the materials.

Digital Imaging of Lithographic Materials by Radical Photopolymerization and Photonic Baking with NIR Diode Lasers

Development of new dyeing photoinitiators based on 6H-indolo[2,3-b]quinoxaline skeleton

Photoinduced Electron Transfer Initiating Systems for Free‐Radical Polymerization

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Photoinduced Electron Transfer Initiating Systems for Free‐Radical Polymerization