Effects of Conjugated Systems on UV-Visible Light-sensitive D-<italic style="font-style: italic">π</italic>-A Type Sulfonium Salt Photoacid Generators

Xing-yu Wu; Jin Ming; Jian-chao Xie; De-cheng Wan; Malval Jean Pierre

doi:10.1007/s10118-016-1863-8

Your Location：

Home >

Browse articles >

Effects of Conjugated Systems on UV-Visible Light-sensitive D-π-A Type Sulfonium Salt Photoacid Generators

Papers | Updated：2021-05-12

- Effects of Conjugated Systems on UV-Visible Light-sensitive D-π-A Type Sulfonium Salt Photoacid Generators
- Chinese Journal of Polymer Science Vol. 34, Issue 12, Pages: 1456-1468(2016)
- Affiliations：
  
  a.School of Materials Science and Engineering, Tongji University, Shanghai 201804, China
  b.Institut de Science des Matériaux de Mulhouse, UMR CNRS 7361, Université de Haute-Alsace, 15 rue Jean Starcky, 68057 Mulhouse, France
- Author bio：
  
  Ming Jin (金明), E-mail:mingjin@tongji.edu.cn
- Funds：
- DOI：10.1007/s10118-016-1863-8
  CLC：
Scan for full text
Xing-yu Wu, Jin Ming, Jian-chao Xie, et al. Effects of Conjugated Systems on UV-Visible Light-sensitive D-π-A Type Sulfonium Salt Photoacid Generators. [J]. Chinese Journal of Polymer Science 34(12):1456-1468(2016)
DOI：

Xing-yu Wu, Jin Ming, Jian-chao Xie, et al. Effects of Conjugated Systems on UV-Visible Light-sensitive D-π-A Type Sulfonium Salt Photoacid Generators. [J]. Chinese Journal of Polymer Science 34(12):1456-1468(2016) DOI： 10.1007/s10118-016-1863-8.

摘要

Abstract

A series of D-,π,-A type sulfonium salt photoacid generators with different ,π,-conjugated structures, such as triphenyl, phenylstilbene, styryl-biphenyl, and stilbene, were designed to determine the effect of molecular structures on the photochemical and photophysical properties. The mechanisms of photochemical generation of H,+, were studied by UV-Vis spectroscopy, theoretical calculations, and fluorescence spectroscopy. It is found that the frontier orbits determine the absorption, the molar extinction coefficients, and the quantum yields of photoacid generation. Triphenyl systems connected with sulfonium are beneficial to increase the quantum yields of acid generation. The photoreactivity of four sulfonium salts was further evaluated through the polymerizations of various epoxide monomers at different irradiation wavelengths (365-425 nm) by using the real-time infrared spectroscopy with light-emitting diodes. The high quantum yields for acid generation (,Φ,H,+,=~0.32 to 0.58) and the high molar extinction coefficients (,ε,=~23500 L·mol,-1,·cm,-1, to 31000 L·mol,-1,·cm,-1,) of the sulfonium salts lead to high conversion rates (over 50%-80%). Hence, these photoinitiators exhibit potential for the photocuring applications.

关键词

Keywords

Sulfonium saltPhotoacid generatorsπ-conjugated structures

references

J.V. Crivello , J.H.W. Lam . Macromolecules , 1977 . 10 (6 ):1307 DOI:10.1021/ma60060a028http://doi.org/10.1021/ma60060a028.

P. Beak , T.A. Sullivan . J. Am. Chem. Soc. , 1982 . 104 (16 ):4450 DOI:10.1021/ja00380a020http://doi.org/10.1021/ja00380a020.

F.D. Saeva , B.P. Morgan . J. Am. Chem. Soc. , 1984 . 106 (15 ):4121 DOI:10.1021/ja00327a010http://doi.org/10.1021/ja00327a010.

Fouassier, J.P. and Lalevée, J., "Photoinitiator for polymer synthesis-scope, reactivity, and efficiency", Wiley-VCH Berlag GmbH & Co. KGaA, Weinheim, 2012

Davidson, S., "Exploring the science, technology and application of UV and EB curing", Sita Technolgy Ltd, London, 1999

J.P. Fouassier . "Photoinitiator, photopolymerization and photocuring:fundamentals and applications" , :New York Hanser Publishers , 1995 .

Cordon, C. and Miller, C., "UV-LED:presented by RadTech-the association for UV & EB technology", RadTech International, Bethesda, 2013

G. Liu , X. Zhu , B. Xu , X. Qian , G. Song , J. Nie . J. Appl. Polym. Sci. , 2013 . 130 (5 ):3698 DOI:10.1002/app.39612http://doi.org/10.1002/app.39612.

X. Sui , X. Feng , A. di Luca , C.A. van Blitterswijk , L. Moroni , M.A. Hempenius , G.J. Vancso . Polym. Chem. , 2013 . 4 (2 ):337 DOI:10.1039/C2PY20431Bhttp://doi.org/10.1039/C2PY20431B.

M.A. Tehfe , F. Dumur , B. Graff , F. Morlet-Savary , J.P. Fouassier , D. Gigmes , J. Lalevée . Macromolecules , 2012 . 45 (21 ):8639 DOI:10.1021/ma301931phttp://doi.org/10.1021/ma301931p.

Z. Walsh , P.A. Levkin , V. Jain , B. Paull , F. Svec , M. Macka . J. Sep. Sci. , 2010 . 33 (1 ):61 DOI:10.1002/jssc.v33:1http://doi.org/10.1002/jssc.v33:1.

P. Xiao , M. Frigoli , F. Dumur , B. Graff , D. Gigmes , J.P. Fouassier , J. Lalevée . Macromolecules , 2014 . 47 (1 ):106 DOI:10.1021/ma402196phttp://doi.org/10.1021/ma402196p.

C. Dietlin , S. Schweizer , P. Xiao , J. Zhang , F. Morlet-Savary , B. Graff , J.P. Fouassier , J. Lalevée . Polym. Chem. , 2015 . 6 (21 ):3895 DOI:10.1039/C5PY00258Chttp://doi.org/10.1039/C5PY00258C.

M.A. Tehfe , F. Dumur , P. Xiao , M. Delgove , B. Graff , J.P. Fouassier , D. Gigmes , J. Lalevée . Polym. Chem. , 2014 . 5 (2 ):382 DOI:10.1039/C3PY00922Jhttp://doi.org/10.1039/C3PY00922J.

P. Xiao , W. Hong , Y. Li , F. Dumur , B. Graff , J.P. Fouassier , D. Gigmes , J. Lalevée . Polym. Chem. , 2014 . 5 (7 ):2293 DOI:10.1039/c3py01599hhttp://doi.org/10.1039/c3py01599h.

J. Zhang , N. Zivic , F. Dumur , P. Xiao , B. Graff , D. Gigmes , J.P. Fouassier , J. Lalevée . J. Polym. Sci., Part A:Polym. Chem. , 2015 . 53 (3 ):445 DOI:10.1002/pola.v53.3http://doi.org/10.1002/pola.v53.3.

F.D. Saeva , E. Garcia , P.A. Martic . J. Photochem. Photobiol. A-Chem. , 1995 . 86 (1-3 ):149 DOI:10.1016/1010-6030(94)03923-Ihttp://doi.org/10.1016/1010-6030(94)03923-I.

W.H. Zhou , S.M. Kuebler , K.L. Braun , T.Y. Yu , J.K. Cammack , C.K. Ober , J.W. Perry , S.R. Marder . Science , 2002 . 296 (5570 ):1106 DOI:10.1126/science.296.5570.1106http://doi.org/10.1126/science.296.5570.1106.

C.O. Yanez , C.D. Andrade , K.D. Belfield . Chem. Commun. , 2009 . 0 (7 ):827 .

R. Xia , J.P. Malval , M. Jin , A. Spangenberg , D. Wan , H. Pu , T. Vergote , F. Morlet-Savary , H. Chaumeil , P. Baldeck , O. Poizat , O. Soppera . Chem. Mater. , 2012 . 24 (2 ):237 DOI:10.1021/cm2030075http://doi.org/10.1021/cm2030075.

M. Jin , H. Hong , J. Xie , J.P. Malval , A. Spangenberg , O. Soppera , D. Wan , H. Pu , D.L. Versace , T. Leclerc , P. Baldeck , O. Poizat , S. Knopf . Polym. Chem. , 2014 . 5 (16 ):4747 DOI:10.1039/C4PY00424Hhttp://doi.org/10.1039/C4PY00424H.

V. De Waele , M. Hamm , T. Vergote , H. Chaumeil , M. Jin , J.P. Malval , P. Baldeck , O. Poizat . Chem. Mater. , 2015 . 27 (5 ):1684 DOI:10.1021/cm504474ghttp://doi.org/10.1021/cm504474g.

M. Jin , X. Wu , J. Xie , J.P. Malval , D. Wan . RSC Adv. , 2015 . 5 (68 ):55340 DOI:10.1039/C5RA11350Dhttp://doi.org/10.1039/C5RA11350D.

F.D. Saeva , D.T. Breslin , H.R. Luss . J. Am. Chem. Soc. , 1991 . 113 (14 ):5333 DOI:10.1021/ja00014a028http://doi.org/10.1021/ja00014a028.

W. Zhou , S.M. Kuebler , D. Carrig , J.W. Perry , S.R. Marder . J. Am. Chem. Soc. , 2002 . 124 (9 ):1897 DOI:10.1021/ja011186khttp://doi.org/10.1021/ja011186k.

G. Pohlers , J.C. Scaiano , R. Sinta . Chem. Mater. , 1997 . 9 (12 ):3222 DOI:10.1021/cm970587phttp://doi.org/10.1021/cm970587p.

M.J. Frisch , 09 "Gaussian , B.01." Revision , Inc Gaussian . "Gaussian 09, Revision B.01." , :Gaussian Inc Wallingford , 2009 .

B. Fang , M. Jin , X. Wu , Y. Zhang , D. Wan . Dyes Pigment. , 2016 . 126 54 DOI:10.1016/j.dyepig.2015.11.012http://doi.org/10.1016/j.dyepig.2015.11.012.

M. Jin , J. Xie , J.P. Malval , A. Spangenberg , O. Soppera , D.L. Versace , T. Leclerc , H. Pan , D. Wan , H. Pu , P. Baldeck , O. Poizat , S. Knopf . J. Mater. Chem. C , 2014 . 2 (35 ):7201 DOI:10.1039/C4TC00706Ahttp://doi.org/10.1039/C4TC00706A.

M. Jin , H. Xu , H. Hong , J.P. Malval , Y. Zhang , A. Ren , D. Wan , H. Pu . Chem. Commun. , 2013 . 49 (76 ):8480 DOI:10.1039/c3cc43018ahttp://doi.org/10.1039/c3cc43018a.

W.H. Zhou , S.M. Kuebler , D. Carrig , J.W. Perry , S.R. Marder . J. Am. Chem. Soc. , 2002 . 124 (9 ):1897 DOI:10.1021/ja011186khttp://doi.org/10.1021/ja011186k.

F.D. Saeva , D.T. Breslin , H.R. Luss . J. Am. Chem. Soc. , 1991 . 113 (14 ):5333 DOI:10.1021/ja00014a028http://doi.org/10.1021/ja00014a028.

X.Z. Wang , F.D. Saeva , J.A. Kampmeier . J. Am. Chem. Soc. , 1999 . 121 (18 ):4364 DOI:10.1021/ja982932xhttp://doi.org/10.1021/ja982932x.

J. Park , N. Kihara , T. Ikeda , T. Endo . Macromolecules , 1997 . 30 (11 ):3414 DOI:10.1021/ma9610222http://doi.org/10.1021/ma9610222.

S.M. Kuebler , K.L. Braun , W. Zhou , J.K. Cammack , T. Yu , C.K. Ober , S.R. Marder , J.W. Perry . J. Photochem. Photobiol., A , 2003 . 158 (2-3 ):163 DOI:10.1016/S1010-6030(03)00030-3http://doi.org/10.1016/S1010-6030(03)00030-3.

Y. Yagci , S. Jockusch , N.J. Turro . Macromolecules , 2010 . 43 (15 ):6245 DOI:10.1021/ma1007545http://doi.org/10.1021/ma1007545.

M.A. Tehfe , F. Dumur , E. Contal , B. Graff , F. Morlet-Savary , D. Gigmes , J.P. Fouassier , J. Lalevée . Polym. Chem. , 2013 . 4 (5 ):1625 DOI:10.1039/C2PY20950Khttp://doi.org/10.1039/C2PY20950K.

M.A. Tehfe , J. Lalevée , F. Morlet-Savary , B. Graff , N. Blanchard , J.P. Fouassier . ACS Macro Lett. , 2011 . 1 (1 ):198 .

Views

Downloads

CSCD

Alert me when the article has been cited

Submit

Tools

Publicity Resources

No data

Related Author

No data

Related Institution

No data

⁰

Effects of Conjugated Systems on UV-Visible Light-sensitive D-π-A Type Sulfonium Salt Photoacid Generators

DOI：10.1007/s10118-016-1863-8

摘要

Abstract

关键词

Keywords

references