Research Articles

Photo-initiated disulfide-ene reaction

Expand
  • School of Environmental and Chemical Engineering, Shanghai University, Shanghai 200444, China

Received date: 2016-01-20

  Online published: 2018-03-05

Abstract

Click chemistry has been widely developed and applied to various fields such as polymers, chemical synthesis, and biology. In recent years, thiol-ene reaction as a type of click chemistry has attracted much attention because it is highly efficient and can be photo-initiated without using toxic metal catalysts. In this paper, the method of photo-initiated disulfide-ene chemistry is introduced. To avoid short-comings of thiol-ene chemistry such as ease of oxidation of thiols and various side reactions, photo-ininitated reactions between disulfides and enes as potential and alternative reactions were studied. Experimental data showed that the reaction rate and yield were affected by various reaction conditions such as oxygen, photo-initiators, different reactants and solvents.

Cite this article

LIU Guangyao, MIAO Miao, AN Zesheng . Photo-initiated disulfide-ene reaction[J]. Journal of Shanghai University, 2018 , 24(1) : 83 -91 . DOI: 10.12066/j.issn.1007-2861.1759

References

[1] Kolb H C, Finn M G, Sharpless K B . Click chemistry: diverse chemical function from a few good reactions[J]. Angewandte Chemie International Edition, 2001,40:2004-2021.
[2] 张涛, 郑朝晖, 成煦 , 等. 材料科学中的点击化学[J]. 化学进展, 2008,20(7/8):1091-1101.
[3] Yu B, Justin W C, Charles E H , et al. Sequential thiol-ene/thiol-ene and thiol-ene/thiol-yne reactions as a route to well-defined mono and bis end-functionalized poly (N-isopropylacrylamide)[J]. Journal of Polymer Science. Part A: Polymer Chemistry, 2009,47:3544-3557.
[4] Pounder R J, Stanford M J, Brooks P , et al. Metal free thiol-maleimide ``Click'' reaction as a mild functionalization strategy for degradable polymers[J]. Chemical Communications, 2008,41:5158-5160.
[5] Lutz J F, B$\acute{o}$rner H G, Weichenhan K. Combining ATRP and ``Click'' chemistry: a promising platform toward functional biocompatible polymers and polymer bioconjugates[J]. Macromolecules, 2006,39:6376-6383.
[6] Harvison M A, Lowe A B . Nucleophile-initiated thiol-michael reactions: effect of organocatalyst, thiol, and ene[J]. Macromolecules Rapid Communications, 2011,32:779-800.
[7] Alessandro D . The emergence of thiol-ene coupling as a click process for materials and bioorganic chemistry[J]. Angewandte Chemie International Edition, 2008,47:2-5.
[8] Killops K L, Campos L M, Hawker C J . Robust, efficient, and orthogonal synjournal of dendrimers via thiol-ene ``Click'' chemistry[J]. Journal of the American Chemical Society, 2008,130:5062-5064.
[9] Altintas O, Hizal G, Tunca U . ABC-type hetero-arm star terpolymers through "Click" chemistry[J]. Journal of Polymer Science. Part A: Polymer Chemistry, 2006,44:5699-5707.
[10] Otsuka H, Nagano S, Kobashi Y , et al. A dynamic covalent polymer driven by disulfide metajournal under photoirradiation[J]. Chemical Communications, 2010,46:1150-1152.
[11] Chan J W, Hoyle C E, Lowe A B , et al. Nucleophile-initiated thiol-michael reactions: effect of organocatalyst, thiol, and ene[J]. Macromolecules, 2010,43:6381-6388.
[12] Lalev$\acute{e}$e J, Fabrice M S, Mohamad E R , et al. Thiyl radical generation in thiol or disulfide containing photosensitive systems[J]. Macromolecular Chemistry and Physics, 2010,211(1):103-110.
[13] Hoyle C E, Lee T Y, Roper T . Thiol-enes: chemistry of the past with promise for the future[J]. Journal of Polymer Science. Part A: Polymer Chemistry, 2004,42:5301-5338.
[14] Hoyle C E, Bowman C N . Thiol-ene click chemistry[J]. Angewandte Chemie International Edition, 2010,49:1540-1573.
[15] Campos L M, Meinel I, Guino R G , et al. Highly versatile and robust materials for soft imprint lithography based on thiol-ene click chemistry[J]. Advanced Materials, 2008,20:1-6.
[16] Uygun M, Tasdelen M A, Yagci Y . Influence of type of initiation on thiol-ene ``Click'' chemistry[J]. Macromolecular Chemistry and Physics, 2010,211(1):103-110.
Outlines

/