Thioxanthone-fluorenes as visible light photoinitiators for free radical polymerization

Gorkem Yilmaz; Binnur Aydogan; Gokhan Temel; Nergis Arsu; Norbert Moszner; Yusuf Yagci

doi:10.1021/ma100371y

Thioxanthone-fluorenes as visible light photoinitiators for free radical polymerization

Gorkem Yilmaz, Binnur Aydogan, Gokhan Temel, Nergis Arsu, Norbert Moszner, Yusuf Yagci^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

133 Citations (Scopus)

Abstract

Two thioxanthone derivatives with fluorene additional chromophoric groups, namely thioxanthone-fluorenecarboxylic acid (TX-FLCOOH) and thioxanthone- fluorene sodium carboxylate (TX-FLCOONa), as visible light absorbing oil- and water-soluble photoinitiators, respectively, were synthesized and characterized. Their ability to initiate photopolymerization of methyl methacrylate (MMA), 2-(2-phosphonoethoxymethyl)acrylic acid ethyl ester (EAEPA), and a multifunctional monomer, trimethylolpropane triacrylate (TMPTA), were examined. The initiation efficiency of TX-FLCOOH was compared with the parent thioxantone (TX) both in the presence and in the absence of a co-initiator, and TX-FLCOOH was found to be more effective in all cases. Photopolymerization and laser flash photolysis studies revealed that depending on the concentration initiation by TX-FLCOOH occurs by intra- and intermolecular H-abstraction of the triplet ³(TX-FLCOOH)*. No polymerization was observed when TX-FLCOONa was used as photoinitiator in the absence of a co-initiator. However, TX-FLCOONa acts as an efficient initiator in the visible range in the presence of H donors in water.

Original language	English
Pages (from-to)	4520-4526
Number of pages	7
Journal	Macromolecules
Volume	43
Issue number	10
DOIs	https://doi.org/10.1021/ma100371y
Publication status	Published - 25 May 2010

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title = "Thioxanthone-fluorenes as visible light photoinitiators for free radical polymerization",

abstract = "Two thioxanthone derivatives with fluorene additional chromophoric groups, namely thioxanthone-fluorenecarboxylic acid (TX-FLCOOH) and thioxanthone- fluorene sodium carboxylate (TX-FLCOONa), as visible light absorbing oil- and water-soluble photoinitiators, respectively, were synthesized and characterized. Their ability to initiate photopolymerization of methyl methacrylate (MMA), 2-(2-phosphonoethoxymethyl)acrylic acid ethyl ester (EAEPA), and a multifunctional monomer, trimethylolpropane triacrylate (TMPTA), were examined. The initiation efficiency of TX-FLCOOH was compared with the parent thioxantone (TX) both in the presence and in the absence of a co-initiator, and TX-FLCOOH was found to be more effective in all cases. Photopolymerization and laser flash photolysis studies revealed that depending on the concentration initiation by TX-FLCOOH occurs by intra- and intermolecular H-abstraction of the triplet 3(TX-FLCOOH)*. No polymerization was observed when TX-FLCOONa was used as photoinitiator in the absence of a co-initiator. However, TX-FLCOONa acts as an efficient initiator in the visible range in the presence of H donors in water.",

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AU - Moszner, Norbert

AU - Yagci, Yusuf

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N2 - Two thioxanthone derivatives with fluorene additional chromophoric groups, namely thioxanthone-fluorenecarboxylic acid (TX-FLCOOH) and thioxanthone- fluorene sodium carboxylate (TX-FLCOONa), as visible light absorbing oil- and water-soluble photoinitiators, respectively, were synthesized and characterized. Their ability to initiate photopolymerization of methyl methacrylate (MMA), 2-(2-phosphonoethoxymethyl)acrylic acid ethyl ester (EAEPA), and a multifunctional monomer, trimethylolpropane triacrylate (TMPTA), were examined. The initiation efficiency of TX-FLCOOH was compared with the parent thioxantone (TX) both in the presence and in the absence of a co-initiator, and TX-FLCOOH was found to be more effective in all cases. Photopolymerization and laser flash photolysis studies revealed that depending on the concentration initiation by TX-FLCOOH occurs by intra- and intermolecular H-abstraction of the triplet 3(TX-FLCOOH)*. No polymerization was observed when TX-FLCOONa was used as photoinitiator in the absence of a co-initiator. However, TX-FLCOONa acts as an efficient initiator in the visible range in the presence of H donors in water.

AB - Two thioxanthone derivatives with fluorene additional chromophoric groups, namely thioxanthone-fluorenecarboxylic acid (TX-FLCOOH) and thioxanthone- fluorene sodium carboxylate (TX-FLCOONa), as visible light absorbing oil- and water-soluble photoinitiators, respectively, were synthesized and characterized. Their ability to initiate photopolymerization of methyl methacrylate (MMA), 2-(2-phosphonoethoxymethyl)acrylic acid ethyl ester (EAEPA), and a multifunctional monomer, trimethylolpropane triacrylate (TMPTA), were examined. The initiation efficiency of TX-FLCOOH was compared with the parent thioxantone (TX) both in the presence and in the absence of a co-initiator, and TX-FLCOOH was found to be more effective in all cases. Photopolymerization and laser flash photolysis studies revealed that depending on the concentration initiation by TX-FLCOOH occurs by intra- and intermolecular H-abstraction of the triplet 3(TX-FLCOOH)*. No polymerization was observed when TX-FLCOONa was used as photoinitiator in the absence of a co-initiator. However, TX-FLCOONa acts as an efficient initiator in the visible range in the presence of H donors in water.

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Thioxanthone-fluorenes as visible light photoinitiators for free radical polymerization

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