Sequential Control over Thiol Click Chemistry by a Reversibly Photoactivated Thiol Mechanism of Spirothiopyran

作者: Zhenzhen Liu , Tao Liu , Qiuning Lin , Chunyan Bao , Linyong Zhu

DOI: 10.1002/ANIE.201409097

关键词:

摘要: A novel photocontrolled thiol click chemistry based on spirothiopyran and maleimide is reported. Upon irradiation with λ=365 nm light, the can isomerize to open merocyanine form, a thiophenolate group, which rapidly react maleimide. The unreacted MC will readily back starting spirothiopyran, be repeatedly photoactivated as needed. Thus, this reversible confers spatiotemporal sequential control thiol–maleimide reaction using only one type of photochemical reaction. Polymer post-functionalization hydrogel building subsequent multipatterning different molecules in temporal manner indicate that Michael addition modulate specific chemical events sequence.

参考文章(40)
Vladimir I. Minkin, Photo-, thermo-, solvato-, and electrochromic spiroheterocyclic compounds. Chemical Reviews. ,vol. 104, pp. 2751- 2776 ,(2004) , 10.1021/CR020088U
K. Barry Sharpless, M. G. Finn, Hartmuth C. Kolb, Click Chemistry: Diverse Chemical Function from a Few Good Reactions. Angewandte Chemie. ,vol. 40, pp. 2004- 2021 ,(2001) , 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.3.CO;2-X
Ryan M. Hensarling, Vanessa A. Doughty, Justin W. Chan, Derek L. Patton, "Clicking" polymer brushes with thiol-yne chemistry: indoors and out. Journal of the American Chemical Society. ,vol. 131, pp. 14673- 14675 ,(2009) , 10.1021/JA9071157
Kuen Yong Lee, David J. Mooney, Hydrogels for tissue engineering. Chemical Reviews. ,vol. 101, pp. 1869- 1879 ,(2001) , 10.1021/CR000108X
Cole A. DeForest, Brian D. Polizzotti, Kristi S. Anseth, Sequential click reactions for synthesizing and patterning three-dimensional cell microenvironments Nature Materials. ,vol. 8, pp. 659- 664 ,(2009) , 10.1038/NMAT2473
Christian Wendeln, Ishwar Singh, Stefan Rinnen, Christian Schulz, Heinrich F. Arlinghaus, Glenn A. Burley, Bart Jan Ravoo, Orthogonal, metal-free surface modification by strain-promoted azide–alkyne and nitrile oxide–alkene/alkyne cycloadditions Chemical Science. ,vol. 3, pp. 2479- 2484 ,(2012) , 10.1039/C2SC20555F
Brian J Adzima, Youhua Tao, Christopher J Kloxin, Cole A DeForest, Kristi S Anseth, Christopher N Bowman, None, Spatial and temporal control of the alkyne–azide cycloaddition by photoinitiated Cu(II) reduction Nature Chemistry. ,vol. 3, pp. 256- 259 ,(2011) , 10.1038/NCHEM.980
Yasuhiro Shiraishi, Kazuya Tanaka, Eri Shirakawa, Yoshitsune Sugano, Satoshi Ichikawa, Shunsuke Tanaka, Takayuki Hirai, Light‐Triggered Self‐Assembly of Gold Nanoparticles Based on Photoisomerization of Spirothiopyran Angewandte Chemie. ,vol. 52, pp. 8304- 8308 ,(2013) , 10.1002/ANIE.201302430
C. Remzi Becer, Richard Hoogenboom, Ulrich S. Schubert, Click Chemistry beyond Metal-Catalyzed Cycloaddition Angewandte Chemie. ,vol. 48, pp. 4900- 4908 ,(2009) , 10.1002/ANIE.200900755
Ryan G. Wylie, Shoeb Ahsan, Yukie Aizawa, Karen L. Maxwell, Cindi M. Morshead, Molly S. Shoichet, Spatially controlled simultaneous patterning of multiple growth factors in three-dimensional hydrogels Nature Materials. ,vol. 10, pp. 799- 806 ,(2011) , 10.1038/NMAT3101