Thiol-yne click polymerization

Chinese Science Bulletin

Volumn 58, Issue 22, 2013, Pages 2711-2718

  Yao, BiCheng ^a   Sun, JingZhi ^a   Qin, AnJun ^a   Tang, Ben Zhong ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

amine; function; radical mechanism; rhodium complex; thiol yne click polymerization

Indexed keywords

EID: 84881616191     PISSN: 10016538     EISSN: 18619541     Source Type: Journal    
DOI: 10.1007/s11434-013-5892-1     Document Type: Review

References (46)

1. Liu J Z, Lam J W Y, Tang B Z. Acetylenic polymers: Syntheses, structures and functions. Chem Rev, 2009, 109: 5799-5867.
2. Kolb H C, Finn M G, Sharpless K B. Click chemistry: Diverse chemical function from a few good reactions. Angew Chem Int Ed, 2001, 40: 2004-2021.
3. Qin A J, Lam J W Y, Tang B Z. Click polymerization. Chem Soc Rev, 2010, 39: 2522-2544.
4. Li H K, Sun J Z, Qin A J, et al. Azide-alkyne click polymerization: An update. Chin J Polym Sci, 2012, 30: 1-15.
5. Qin A J, Lam J W Y, Tang B Z. Click polymerization: Progresses, challenges, and opportunities. Macromolecules, 2010, 43: 8693-8702.
6. Wan X J, Xu J, Liu S Y. Facile synthesis of dendrimer-like star-branched poly(isopropylacrylamide) via combination of click chemistry and atom transfer radical polymerization. Sci China-Chem, 2010, 53: 2520-2527.
7. Hoogenboom R. Thiol-yne chemistry: A powerful tool for creating highly functional materials. Angew Chem Int Ed, 2010, 49: 3415-3417.
8. Killops K L, Campos L M, Hawker C J. Robust, efficient, and orthogonal synthesis of dendrimers via thiol-ene "click" chemistry. J Am Chem Soc, 2008, 130: 5062-5064.
9. Kade M J, Burke D J, Hawker C J. The power of thiol-ene chemistry. J Polym Sci Part A: Polym Chem, 2010, 48: 743-750.
10. Hoyle C E, Bowman C N. Thiol-ene click chemistry. Angew Chem Int Ed, 2010, 49: 1540-1573.
11. Altintas O, Barner-Kowollik C, Tunca U, et al. Constructing star polymers via modular ligation strategies. Polym Chem, 2012, 3: 34-35.
12. Tasdelen M A. Diels-Alder "click" reactions: Recent applications in polymer and material science. Polym Chem, 2011, 2: 2133-2145.
13. Wang C, Huang X J, Ren B F, et al. Glycosylation of polymer membrane surface by thiol-yne click chemistry for lectin affinity adsorption. Chem Commun, 2011, 47: 3930-3932.
14. Bader H, Heilbron I, Jones E R H, et al. The addition of thiolacetic acid to acetylenic hydrocarbons. The conversion of monosubstituted acetylenes into aldehydes and 1: 2-dithiols. J Chem Soc, 1949, 619-623.
15. Lowe A B, Hoyleb C E, Bowman C N. Thiol-yne click chemistry: A powerful and versatile methodology for materials synthesis. J Mater Chem, 2010, 20: 4745-4750.
16. Fairbanks B D, Anseth K S, Bowman C N, et al. Thiol-yne photopolymerizations: Novel mechanism, kinetics, and step-growth formation of highly cross-linked networks. Macromolecules, 2009, 42: 211-217.
17. Jim C K W, Qin A, Lam J W Y, et al. Metal-free alkyne polyhydrothiolation: Synthesis of functional poly(vinylenesulfide)s with high stereoregularity by regioselective thioclick polymerization. Adv Funct Mater, 2010, 20: 1319-1328.
18. Liu J, Lam J W Y, Jim C K W, et al. Thiol-yne click polymerization: Regio- and stereoselective synthesis of sulfur-rich acetylenic polymers with controllable chain conformations and tunable optical properties. Macromolecules, 2011, 44: 68-79.
19. Han J, Gao Y, Gao C, et al. Fast and scalable production of hyperbranched polythioether-ynes by a combination of thiol-halogen click-like coupling and thiol-yne click polymerization. Polym Chem, 2012, 3: 1918-1925.
20. 2 approach. Polym Chem, 2011, 2: 2175-2178.
21. Konkolewicz D, Gray-Wealeb A, Perrier S. Hyperbranched polymers by thiol-yne chemistry: From small molecules to functional polymers. J Am Chem Soc, 2009, 131: 18075-18077.
22. Konkolewicz D, Gray-Wealeb A, Perrier S, et al. Hyperbranched alternating block copolymers using thiol-yne chemistry: Materials with tuneable properties. Chem Commun, 2011, 47: 239-241.
23. Liu W, Dong C M. Versatile strategy for the synthesis of hyperbranched poly(e{open}-caprolactone)s and polypseudorotaxanes thereof. Macromolecules, 2010, 43: 8447-8455.
24. Fairbanks B D, Anseth K S, Bowman C N, et al. Reaction rates and mechanisms for radical, photoinitated addition of thiols to alkynes, and implications for thiol-yne photopolymerizations and click reactions. Macromolecules, 2010, 43: 4113-4119.
25. Fairbanks B D, Anseth K S, Bowman C N, et al. Thiol-yne photopolymerizations: Novel mechanism, kinetics, and step-growth formation of highly cross-linked networks. Macromolecules, 2009, 42: 211-217.
26. Chan J W, Hoyle C E, Lowe A B, et al. Photopolymerization of thiolalkynes: Polysulfide networks. Chem Mater, 2009, 21: 1579-1585.
27. Chan J W, Bowman C N, Lowe A B, et al. Synthesis, thiol-yne "click" photopolymerization, and physical properties of networks derived from novel multifunctional alkynes. Macromolecules, 2010, 43: 4937-4942.
28. Turunc O, Meier M A R. A novel polymerization approach via thiolyne addition. J Polym Sci Part A: Polym Chem, 2012, 50: 1689-1695.
29. Lomba M, Serrano J L, Fuente J M D, et al. In situ photopolymerization of biomaterials by thiol-yne click chemistry. Macromol Biosci, 2011, 11: 1505-1514.
30. Jikei M, Kakimoto M. Hyperbranched polymers: A promising new class of materials. Prog Polym Sci, 2001, 26: 1233-1285.
31. Gao C, Yan D Y. Hyperbranched polymers: From synthesis to applications. Prog Polym Sci, 2004, 29: 183-275.
32. Häußler M, Qin A J, Tang B Z. Acetylenes with multiple triple bonds: A group of versatile An-type building blocks for the construction of functional hyperbranched polymers. Polymer, 2007, 48: 6181-6204.
33. Voit B I, Lederer A. Hyperbranched and highly branched polymer architectures-synthetic strategies and major characterization aspects. Chem Rev, 2009, 109: 5924-5973.
34. Hensarling R M, Chan J W, Patton D L, et al. "Clicking" polymer brushes with thiol-yne chemistry: Indoors and out. J Am Chem Soc, 2009, 131: 14673-14675.
35. Qin A J, Jim C K W, Lu W X, et al. Click polymerization: Facile synthesis of functional poly(aroyltriazole)s by metal-free, regioselective 1, 3-dipolar Polycycloaddition. Macromolecules, 2007, 40: 2308-2317.
36. Qin A J, Tang L, Lam J W Y, et al. Metal-free click polymerization: Synthesis and photonic properties of poly(aroyltriazole)s. Adv Funct Mater, 2009, 19: 1891-1900.
37. Li H K, Mei J, Wang J, et al. Facile synthesis of poly(aroxycar-bonyltriazole)s with aggregation-induced emission characteristics by metal-free click polymerization. Sci China-Chem, 2011, 54: 611-616.
38. Li H K, Wang J, Sun J Z, et al. Metal-free click polymerization of propiolates and azides: Facile synthesis of functional poly(aroxycarbonyltriazole)s. Polym Chem, 2012, 3: 1075-1083.
39. Wei Q, Wang J, Shen X Y, et al. Self-healing hyperbranched poly(aroyltriazole)s. Sci Rep, 2013, 3: 1093.
40. Gokmen M T, Prasath R A, Du Prez F E, et al. Revealing the nature of thio-click reactions on the solid phase. Chem Commun, 2011, 47: 4652-4654.
41. Kuniyasu H, Ogawa A, Sonoda N, et al. The first example of transition-metal-catalyzed addition of aromatic thiols to acetylenes. J Am Chem Soc, 1992, 114: 5902-5903.
42. Munro-Leighton C, Delp S A, Gunnoe T B, et al. Anti-Markovnikov hydroamination and hydrothiolation of electron-deficient vinylarenes catalyzed by well-defined monomeric copper (I) amido and thiolate complexes. Chem Commun, 2008, 111-113.
43. Ananikov V P, Khrustalev V N, Antipin M Y, et al. Two distinct mechanisms of alkyne insertion into the metal-sulfur bond: combined experimental and theoretical study and application in catalysis. Chem Eur J, 2010, 16: 2063-2071.
44. Giuseppe A D, Castarlenas R, Polo V, et al. Ligand-controlled regioselectivity in the hydrothiolation of alkynes by rhodium N-hetero-cyclic carbene catalysts. J Am Chem Soc, 2012, 134: 8171-8183.
45. Ananikov V P, Aleksandrov G G, Eremenko I L, et al. Nickel (II) chloride-catalyzed regioselective hydrothiolation of alkynes. Adv Synth Catal, 2005, 347: 1993-2001.
46. Yang Y, Rioux R M. Highly regio- and stereoselective hydrothiolation of acetylenes with thiols catalyzed by a well-defined supported Rh complex. Chem Commun, 2011, 6557-6559.