Photoinitiated cationic polymerization using <i>o</i>‐phthaldehyde and pyridinium salt

Yaǧcı, Yusuf; Denizligil, Selçuk

doi:10.1002/pola.1995.080330907

Cited by 20 publications

(8 citation statements)

References 18 publications

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“…The acid generation proceeds through a photoinduced electron transfer (PeT) from the excited chromophores to the PAG. Another elegant strategy, namely the free radical promoted cationic polymerization (FRPCP), 9,[21][22][23][24][25][26][27][28][29][30] concerns the use of photogenerated radicals (Rc) as strong reductants, which are oxidized by iodonium or sulfonium salts. All these sensitizing methods can be directly transposed to two-photon excitation.…”

Section: Introductionmentioning

confidence: 99%

π-conjugated sulfonium-based photoacid generators: an integrated molecular approach for efficient one and two-photon polymerization

et al. 2014

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Section: Introductionmentioning

confidence: 99%

π-conjugated sulfonium-based photoacid generators: an integrated molecular approach for efficient one and two-photon polymerization

et al. 2014

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“…Additionally, o-phthaldehyde was employed to promote the cationic polymerization process by the formation of biradicals through intramolecular hydrogen abstraction in the excited state (Scheme 16). 221 Subsequent oxidation of the biradicals by pyridinium salt and further decomposition to yield Bronsted acid initiated cationic polymerization. As previously shown, electron transfer reactions from the radicals formed this way to the onium salt oxidize radicals to cationic species that are capable of initiating cationic polymerization of various monomers.…”

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confidence: 99%

Photoinduced Electron Transfer Reactions for Macromolecular Syntheses

2016

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Photochemical reactions, particularly those involving photoinduced electron transfer processes, establish a substantial contribution to the modern synthetic chemistry, and the polymer community has been increasingly interested in exploiting and developing novel photochemical strategies. These reactions are efficiently utilized in almost every aspect of macromolecular architecture synthesis, involving initiation, control of the reaction kinetics and molecular structures, functionalization, and decoration, etc. Merging with polymerization techniques, photochemistry has opened up new intriguing and powerful avenues for macromolecular synthesis. Construction of various polymers with incredibly complex structures and specific control over the chain topology, as well as providing the opportunity to manipulate the reaction course through spatiotemporal control, are one of the unique abilities of such photochemical reactions. This review paper provides a comprehensive account of the fundamentals and applications of photoinduced electron transfer reactions in polymer synthesis. Besides traditional photopolymerization methods, namely free radical and cationic polymerizations, step-growth polymerizations involving electron transfer processes are included. In addition, controlled radical polymerization and "Click Chemistry" methods have significantly evolved over the last few decades allowing access to narrow molecular weight distributions, efficient regulation of the molecular weight and the monomer sequence and incredibly complex architectures, and polymer modifications and surface patterning are covered. Potential applications including synthesis of block and graft copolymers, polymer-metal nanocomposites, various hybrid materials and bioconjugates, and sequence defined polymers through photoinduced electron transfer reactions are also investigated in detail.

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“…All initiators are able to initiate polymerization of MMA in the absence of additional co‐initiator, confirming the one‐component nature. Hydrogen abstraction in case of TX‐A occurs from the aldehyde group of the initiator, as observed earlier while hydrogen abstraction in case of the new synthesized initiators occurs from the ethyleneamine moiety. Adding TEA however, increases the conversion and leads to polymers with higher average molecular‐weight.…”

Section: Resultsmentioning

confidence: 53%

One‐component, double‐chromophoric thioxanthone photoinitiators for free radical polymerization

Kreutzer

Yaǧcı

2017

J. Polym. Sci. Part A: Polym. Chem.

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Two one‐component, double‐chromophoric thioxanthone photoinitiators, namely TX‐EDA and TX‐DETA were synthesized by the reaction of thioxanthone aldehyde (TX‐A) with ethylenediamine (EDA) and diethylenetriamine (DETA), respectively via a facile Schiff base reaction. Both photoinitiators were characterized by spectral analysis and photobleaching studies. DFT calculations are employed to reveal the contribution of the different orbitals to the excitation of the initiators. The double‐chromophoric nature of the initiators gives rise to an increased absorption in the near UV region when compared with the pristine TX‐A. Photoinitiated polymerization of various vinyl monomers with TX‐EDA and TX‐DETA has been investigated in the presence and absence of a co‐initiator and compared for formulations consisting of precursor TX‐A. In addition, real‐time FTIR spectroscopic studies were performed in methyl methacrylate polymerization with both initiators. The higher efficiency observed with TX‐DETA may be attributed to the additional hydrogen donating sites adjacent to nitrogen atoms. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 3475–3482

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Photoinitiated cationic polymerization using o‐phthaldehyde and pyridinium salt

Cited by 20 publications

References 18 publications

π-conjugated sulfonium-based photoacid generators: an integrated molecular approach for efficient one and two-photon polymerization

π-conjugated sulfonium-based photoacid generators: an integrated molecular approach for efficient one and two-photon polymerization

Photoinduced Electron Transfer Reactions for Macromolecular Syntheses

One‐component, double‐chromophoric thioxanthone photoinitiators for free radical polymerization

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