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

Istanbul Technical University
Yalova University
Yildiz Technical University
Ivoclar Vivadent AG

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

143 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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@article{97c732f1f89746febc3e564ee11afb17,

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.",

author = "Gorkem Yilmaz and Binnur Aydogan and Gokhan Temel and Nergis Arsu and Norbert Moszner and Yusuf Yagci",

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T1 - Thioxanthone-fluorenes as visible light photoinitiators for free radical polymerization

AU - Yilmaz, Gorkem

AU - Aydogan, Binnur

AU - Temel, Gokhan

AU - Arsu, Nergis

AU - Moszner, Norbert

AU - Yagci, Yusuf

PY - 2010/5/25

Y1 - 2010/5/25

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.

UR - https://www.scopus.com/pages/publications/77952502245

U2 - 10.1021/ma100371y

DO - 10.1021/ma100371y

M3 - Article

AN - SCOPUS:77952502245

SN - 0024-9297

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SP - 4520

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JO - Macromolecules

JF - Macromolecules

IS - 10

ER -

Thioxanthone-fluorenes as visible light photoinitiators for free radical polymerization

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