Benzoyl Phenyltelluride as Highly Reactive Visible-Light TERP-Reagent for Controlled Radical Polymerization

被引:22
作者
Benedikt, Stephan [1 ]
Moszner, Norbert [2 ]
Liska, Robert [1 ]
机构
[1] Vienna Univ Technol, Inst Appl Synthet Chem, Div Macromol Chem, A-1060 Vienna, Austria
[2] Ivoclar Vivadent AG, FL-9494 Schaan, Liechtenstein
关键词
CHAIN-TRANSFER; INIFERTER; PHOTOPOLYMERIZATION; PHOTOINIFERTERS; PHOTOIRRADIATION; ULTRAVIOLET; INITIATORS; SPECTRA;
D O I
10.1021/ma5011588
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Benzoyl phenyltelluride (BPT) is a highly reactive TERP-reagent for visible-light-induced (400-500 nm) controlled radical polymerization. The compound can be easily prepared in one step from diphenyl ditelluride and benzoyl chloride. It shows a strong absorption at 407 nm that tails out to 473 rim and provides PDIs (1.2 to 1.3) among the lowest reported in literature for photoiniferters in general, to which our compound was compared. PDIs obtained with BPT are much lower than those for benzyl dithiocarbamte (BDC) (1.7 to 1.8), which was used as a reference compound. Choice of BDC as reference is based on its property as UV-photoiniferter and on a similar initiation/control mechanism. However, BDC does not allow living radical polymerization under visible light. The newly discovered compound BPT provides best results with acrylamides and acrylates. Photoinitiation with styrene was ineffective, and reaction with methacrylates is not considered living.
引用
收藏
页码:5526 / 5531
页数:6
相关论文
共 36 条
[1]   EXCITED ELECTRONIC STATES OF ALPHA-DICARBONYLS [J].
ARNETT, JF ;
NEWKOME, G ;
MATTICE, WL ;
MCGLYNN, SP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (14) :4385-4392
[2]   Responsive polymers in controlled drug delivery [J].
Bajpai, A. K. ;
Shukla, Sandeep K. ;
Bhanu, Smitha ;
Kankane, Sanjana .
PROGRESS IN POLYMER SCIENCE, 2008, 33 (11) :1088-1118
[3]   Living radical polymerization of MMA in the presence of piperidino-dithiocarbamate derivatives as photoiniferters [J].
Bertin, D ;
Boutevin, B ;
Gramain, P ;
Fabre, JM ;
Montginoul, C .
EUROPEAN POLYMER JOURNAL, 1998, 34 (01) :85-90
[4]   A modular approach toward functionalized three-dimensional macromolecules:: From synthetic concepts to practical applications [J].
Bosman, AW ;
Vestberg, R ;
Heumann, A ;
Fréchet, JMJ ;
Hawker, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (03) :715-728
[5]  
Bromme T., 2012, EUR COAT J, V20-21, P24
[6]   Living free-radical polymerization by reversible addition-fragmentation chain transfer: The RAFT process [J].
Chiefari, J ;
Chong, YK ;
Ercole, F ;
Krstina, J ;
Jeffery, J ;
Le, TPT ;
Mayadunne, RTA ;
Meijs, GF ;
Moad, CL ;
Moad, G ;
Rizzardo, E ;
Thang, SH .
MACROMOLECULES, 1998, 31 (16) :5559-5562
[7]   An ultraviolet-curable mold for sub-100-nm lithography [J].
Choi, SJ ;
Yoo, PJ ;
Baek, SJ ;
Kim, TW ;
Lee, HH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (25) :7744-7745
[8]   Living free radical photopolymerization initiated from surface-grafted iniferter monolayers [J].
de Boer, B ;
Simon, HK ;
Werts, MPL ;
van der Vegte, EW ;
Hadziioannou, G .
MACROMOLECULES, 2000, 33 (02) :349-356
[9]   Overview of cobalt-mediated radical polymerization: Roots, state of the art and future prospects [J].
Debuigne, Antoine ;
Poli, Rinaldo ;
Jerome, Christine ;
Jerome, Robert ;
Detrembleur, Christophe .
PROGRESS IN POLYMER SCIENCE, 2009, 34 (03) :211-239
[10]   New photocleavable structures. Diacylgermane-based photoinitiators for visible light curing [J].
Ganster, Beate ;
Fischer, Urs Karl ;
Moszner, Norbert ;
Liska, Robert .
MACROMOLECULES, 2008, 41 (07) :2394-2400