Thioxanthene-9-thione Mediated MMA Polymerization

Xu Yan; Guan Wang; Li-Hua Zhang; Li Wang; Xiao-Fei Liu; Wan-Tai Yang

doi:10.1007/s10118-018-2140-9

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Thioxanthene-9-thione Mediated MMA Polymerization

RAPID COMMUNICATION | Updated：2021-02-18

- Thioxanthene-9-thione Mediated MMA Polymerization
- Chinese Journal of Polymer Science Vol. 36, Issue 7, Pages: 805-810(2018)
- Affiliations：
  
  a.State Key Laboratory of Chemical Resource Engineering, Beijing University of Chemical and Technology, Beijing 100029, China
  b.Beijing Laboratory of Biomedical Materials Polymer Materials, Beijing University of Chemical and Technology, Beijing 100029, China
- Author bio：
  
  yangwt@mail.buct.edu.cn
- Funds：
- DOI：10.1007/s10118-018-2140-9
  CLC：
- Received：06 March 2018，
  
  Revised：2018-3-29，
  
  Accepted：30 March 2018，
  
  Online First：27 April 2018，
  
  Published：2018-07
- Accepted：
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Xu Yan, Guan Wang, Li-Hua Zhang, et al. Thioxanthene-9-thione Mediated MMA Polymerization[J]. Chinese Journal of Polymer Science, 2018, 36(7): 805-810.
DOI：

Xu Yan, Guan Wang, Li-Hua Zhang, et al. Thioxanthene-9-thione Mediated MMA Polymerization[J]. Chinese Journal of Polymer Science, 2018, 36(7): 805-810. DOI： 10.1007/s10118-018-2140-9.

摘要

Abstract

In the " cycloketyl radical mediated living polymerization” (CMP) process

a cycloketyl compound

9′]bixanthenyl-9

9′ diol (BIXAN) was ultilized as initiator and mediator. The cycloketyl (CK) radical was used as the dormant radical to achieve the increase of molecular weight. Herein

a series of cycloketyl thioketones were synthesised by Lawesson’s reagent by one step reaction with high yeild

and we found that

when a special cycloketyl thioketone compound

thioxanthene-9-thione (TXT)

was added to a routine radical polymerization system

TXT could capture chain radical

and simultaneously formed an radical analogous to CK radical in structure

which could trigger the growth of polymer chains. This simple system was efficient to initiate the polymerization of methyl methacrylate (MMA) and in all cases the molecular weights increased with the increase of conversions. By the end-group analysis with

H-NMR and MALDI-TOF MS

it was confirmed that the P-STXT radical was used to control the polymerization. The re-initiating reactions were achieved when PMMA was used as the macro-initiator.

关键词

Keywords

references

Hawker, C. J.; Bosman, A. W.; Harth, E . New polymer synthesis by nitroxide mediated living radical polymerizations . Chem. Rev. , 2001 . 101 3661 - 3688 . DOI: 10.1021/cr990119u http://doi.org/10.1021/cr990119u .

Nicolas, J.; Guillaneuf, Y.; Lefay, C.; Bertin, D.; Gigmes, D.; Charleux, B . Nitroxide-mediated polymerization . Prog. Polym. Sci. , 2013 . 38 63 - 235 . DOI: 10.1016/j.progpolymsci.2012.06.002 http://doi.org/10.1016/j.progpolymsci.2012.06.002 .

Matyjaszewski, K . Atom transfer radical polymerization . Chem. Rev. , 2001 . 101 2921 - 2990 . DOI: 10.1021/cr940534g http://doi.org/10.1021/cr940534g .

Matyjaszewski, K.; Tsarevsky, N. V . Macromolecular, engineering by atom transfer radical polymerization . J. Am. Chem. Soc. , 2014 . 136 6513 - 6533 . DOI: 10.1021/ja408069v http://doi.org/10.1021/ja408069v .

Moad, G.; Rizzardo, E.; Thang. S. H . Radical addition-fragmentation chemistry in polymer synthesis . Polymer , 2008 . 49 1079 - 1131 . DOI: 10.1016/j.polymer.2007.11.020 http://doi.org/10.1016/j.polymer.2007.11.020 .

Yagci, Y.; Tasdelen, M. A . Mechanistic transformations involving living and controlled/living polymerization methods . Prog. Polym. Sci. , 2006 . 31 1133 - 1170 . DOI: 10.1016/j.progpolymsci.2006.07.003 http://doi.org/10.1016/j.progpolymsci.2006.07.003 .

Magenau, A. J. D.; Strandwitz, N. C.; Matyjaszewski, K . Electrochemically mediated atom transfer radical polymerization . Science , 2011 . 332 81 - 84 . DOI: 10.1126/science.1202357 http://doi.org/10.1126/science.1202357 .

Zheng, X. F.; Yue, M.; Yang, P.; Li, Q.; Yang, W. T . Cycloketyl radical mediated living polymerization . Polym. Chem. , 2012 . 3 1982 - 1986 . DOI: 10.1039/c2py20117h http://doi.org/10.1039/c2py20117h .

Toy, A.; Chaffey-Millar, H.; Davis, T. P.; Stenzel, M. H.; Izgorodina, E. I.; Coote, M. L.; Barner-Kowollik, C . Thioketone spin traps as mediating agents for free radical polymerization processes . Chem. Commun. , 2006 . 8 ( 8 ): 835 - 837 . .

Junkers, T.; Stenzel, M. H.; Davis, T. P.; Barner-Kowollik, C . Controlling free-radical polymerization via a dormant radical species . Macromol. Rapid Commun. , 2007 . 28 746 - 753 . DOI: 10.1002/(ISSN)1521-3927 http://doi.org/10.1002/(ISSN)1521-3927 .

Günzler, F.; Junkers, T.; Barner-Kowollik, C . Studying the mechanism of thioketone-mediated polymerization via electrospray ionization mass spectrometry . J. Polym. Sci., Part A: Polym. Chem. , 2009 . 47 ( 7 ): 1864 - 1876 . DOI: 10.1002/pola.23280 http://doi.org/10.1002/pola.23280 .

Junkers, T.; Delaittre, G.; Chapman, R.; Günzler, F.; Chernikova, E.; Barner-Kowollik, C . Thioketone-mediated polymerization with dithiobenzoates: proof for the existence of stable radical intermediates in RAFT polymerization . Macromol. Rapid Commun. , 2012 . 33 984 - 990 . DOI: 10.1002/marc.201200128 http://doi.org/10.1002/marc.201200128 .

Varma , R. S.; Kumar, D . Microwave-accelerated solvent-free synthesis of thioketones, thiolactones, thioamides, thionoesters, and thioflavonoids . Org. Lett. , 1999 . 1 697 - 700 . DOI: 10.1021/ol990629a http://doi.org/10.1021/ol990629a .

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