Development of new heterobicationic monomethine dyes as effective photoinitiator of free radical polymerization in visible‐light region

Kabatc, Janina; Kaczorowska, Mirosława; Jędrzejewska, Beata; Pączkowski, Jerzy

doi:10.1002/app.27821

Cited by 6 publications

(13 citation statements)

References 25 publications

(48 reference statements)

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“…According to Chatterjee's et al studies on symmetrical cyanine borate initiators,31, 32 in nonpolar or medium polarity solvents, one can treat cyanine cation and borate anion as an ion pair. However, our studies on the influence of the borate anion concentration on the rate of photoinitiated polymerization indicates, for identical monomer‐dye formulation, a distinct increase in the rate of polymerization as the concentration of borate anion increases 15–17. This finding suggests that at the concentration of borate anion equals to the concentration of cyanine cation, only a part of the photoredox pairs exist as the ion pair.…”

Section: Resultsmentioning

confidence: 68%

“…Interesting examples are borate salt initiators. They work by inter‐ or intramolecular photoinduced electron transfer (PET) 12–17. In case of the cyanine borate the polymerization is initiated by an alkyl radical formed as a result of the PET from borate anion to the excited state of cyanine dye, followed by a rapid cleavage of the alkyl boron bond of the boranyl radical (Fig.…”

Section: Introductionmentioning

confidence: 99%

“…The modification of the dye structure by shortening or extending a polymethine chain, by introduction different substituents in heterocyclic moiety or in the “meso” position of polymethine chain leads to the changes in absorption spectra and in the efficiency of the radical polymerization of vinyl monomers 14. From our earlier studies, it is known that the modification of the hemicyanine dye structure by introduction of the second, not conjugated with the dye molecule, quaternary nitrogen significantly enhances the efficiency of the photoinitiation 15–17…”

Section: Introductionmentioning

confidence: 99%

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Studies on an argon laser‐induced photopolymerization employing both mono‐ and bischromophoric hemicyanine dye—Borate complex as a photoinitiator. Part III

Jędrzejewska

Urbański

2010

J of Applied Polymer Sci

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Two series of homodimeric hemicyanine dyes based on 4-(p-N,N-dialkylaminostyryl)pyridinium and 4-(p-N,N-dialkylaminostyryl)quinolinium residues have been evaluated as novel photoinitiators for radical polymerization induced with an argon ion laser visible emission. In the tested photoredox pairs, hemicyanine dye cation acts as an electron acceptor and it is coupled with n-butyltriphenyl borate anion being an electron donor. The photochemistry of the series of bichromophoric stilbazolium borates, 1,3-, 1,5-, and 1,10-bis-[4-(p-N,N-dialkylaminostyryl)pyridinyl]alkane di-n-butyltriphenylborates and 1,3-, 1,5-, and 1,10-bis-[4-(p-N,N-dialkylaminostyryl) quinolinyl]alkane di-n-butyltriphenylborates, was compared with the photochemistry of the structurally related, monochromophoric styrylpyridinium and the styrylquinolinium borates. The experimental results indicated that the rate of photopolymerization depends on DG el of the electron transfer between borate anion and hemicyanine cation. The relationship between the rate of polymerization and the free energy of activation shows the dependence predicted by the classical theory of the electron transfer.

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Section: Resultsmentioning

confidence: 68%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Studies on an argon laser‐induced photopolymerization employing both mono‐ and bischromophoric hemicyanine dye—Borate complex as a photoinitiator. Part III

Jędrzejewska

Urbański

2010

J of Applied Polymer Sci

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“…In summary, their photoinitiating ability is comparable or lower than the photoinitiating ability of well-known commonly used photoinitiators operating in the visible-light region [1, 8, 13, 16–18]. …”

Section: Resultsmentioning

confidence: 97%

“…For example, the modification of the hemicyanine dye structure by introduction of the second, not conjugated with the dye molecule, quaternary nitrogen atom significantly enhances the rate of photoinitiation [8]. …”

Section: Introductionmentioning

confidence: 99%

Visible light-induced polymerization initiated by borate salts of bicationic monochromophoric benzothiazolestyrylium dyes

Kabatc

Jurek

2014

Colloid Polym Sci

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A series of bicationic monochromophoric hemicyanine dyes based on benzothiazolestyrylium residues were synthesized. The dyeing photoinitiating systems consisting of N-[3-(4-methylpyridino)propyl]-2-(p-substituted styryl)benzothiazolium dihalides as chromophores and n-butyltriphenylborate anion as electron donor were also prepared to achieve an efficient photoinitiators for free-radical polymerization in a visible-light region. The relative photoinitiating efficiencies of novel photoinitiators of acrylate monomers polymerization were evaluated.

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Three‐cationic carbocyanine dyes as sensitizers in very efficient photoinitiating systems for multifunctional monomer polymerization

Kabatc¹,

Pączkowski²

2009

J. Polym. Sci. A Polym. Chem.

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This article is focused on the description of the synthesis, spectroscopic, electrochemical properties, and the free radical photoinitiation abilities of new threecationic carbocyanine dyes. A new synthestic strategy for preparation of symmetrical cyanine dyes has been developed based on the 2-methylbenzothiazole, 2-methylbenzoxazole and 2,3,3-trimethylindolinium quaternization by a-bromo-x-tertiary ammonium salts followed by the condensation of obtained product with triethyl ortho-formate. Resulted dyes possess in one molecule three quaternary nitrogen atoms, for example, they are three-cationic in character. Novel three-cationic symmetric carbocyanine dyes paired with n-butyltriphenylborate anions are very efficient photoinitiators of free radical polymerization of acrylate monomers, for example, (TMPTA) when irradiated with the visible emission of an argon-ion laser. The photoinitiating abilities of the novel photoredox pairs were compared to the photoinitiation properties of their monocationic equivalents, for example, N,N 0 -diethylthia-, N,N 0 -diethyloxa-and N,N 0 -dimethylindocarbocyanine n-butyltriphenylborates (SB2, OB2, and IB2) and also compared to the initiation ability of Rose Bengal derivative, for example, typical triplet state photoinitiator. The kinetic studies clearly demonstrated that the three-cationic carbocyanine borate photoredox pairs exhibit a significant increase in the efficiency of TMPTA free radical polymerization in comparison to the photoredox pairs containing structurally related, mono-cationic carbocyanine borates. It was also shown that, the addition of a second coinitiator to the cyanine borate salts enhances their photoinitiating abilities. The best results were obtained for three cationic carbocyanine borates in the presence of second coinitiator being N-methoxypyridinium n-butyltriphenylborate. The photoinitiating abilities of the systems of these types are more effective than those composed of carbocyanine cation/borate anion exclusively. V V C 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: [4636][4637][4638][4639][4640][4641][4642][4643][4644][4645][4646][4647][4648][4649][4650][4651][4652][4653][4654] 2009

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Development of new heterobicationic monomethine dyes as effective photoinitiator of free radical polymerization in visible‐light region

Cited by 6 publications

References 25 publications

Studies on an argon laser‐induced photopolymerization employing both mono‐ and bischromophoric hemicyanine dye—Borate complex as a photoinitiator. Part III

Studies on an argon laser‐induced photopolymerization employing both mono‐ and bischromophoric hemicyanine dye—Borate complex as a photoinitiator. Part III

Visible light-induced polymerization initiated by borate salts of bicationic monochromophoric benzothiazolestyrylium dyes

Three‐cationic carbocyanine dyes as sensitizers in very efficient photoinitiating systems for multifunctional monomer polymerization

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