Light-induced click reactions

Angewandte Chemie - International Edition

Volumn 52, Issue 23, 2013, Pages 5930-5938

  Tasdelen, Mehmet Atilla ^a   Yagci, Yusuf ^b,c  

^a YALOVA UNIVERSITY   (Turkey)

^b ISTANBUL TECHNICAL UNIVERSITY   (Turkey)

^c KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

Author keywords

cycloaddition; Diels Alder reaction; hybrid materials; photochemistry; polymers

Indexed keywords

BIOMOLECULAR SYSTEM; CHEMICAL AND BIOLOGICALS; CLICK REACTION; DIELS-ALDER REACTION; DIVERSE FIELDS; MODERN SCIENCE; SYNTHETIC CHEMISTS; TEMPORAL CONTROLS;

BIOLOGICAL MATERIALS; CYCLOADDITION; HYBRID MATERIALS; LIGHT SOURCES; PHOTOCHEMICAL REACTIONS; POLYMERS;

CHEMICAL REACTIONS;

EID: 84878393371     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201208741     Document Type: Article

References (108)

1. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056-2075
2. Angew. Chem. Int. Ed. 2001, 40, 2004-2021.
3. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708-2711
4. Angew. Chem. Int. Ed. 2002, 41, 2596-2599
5. C. W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057-3064.
6. G. Franc, A. K. Kakkar, Chem. Eur. J. 2009, 15, 5630-5639
7. M. A. Tasdelen, Polym. Chem. 2011, 2, 2133-2145
8. G. Hizal, U. Tunca, A. Sanyal, J. Polym. Sci. Part A 2011, 49, 4103-4120
9. A. Sanyal, Macromol. Chem. Phys. 2010, 211, 1417-1425.
10. G. Kumaraswamy, K. Ankamma, A. Pitchaiah, J. Org. Chem. 2007, 72, 9822-9825.
11. K. L. Heredia, Z. P. Tolstyka, H. D. Maynard, Macromolecules 2007, 40, 4772-4779
12. A. Dirksen, P. E. Dawson, Bioconjugate Chem. 2008, 19, 2543-2548
13. M. Bahta, F. Liu, S. E. Kim, A. G. Stephen, R. J. Fisher, T. R. Burke, Nat. Protoc. 2012, 7, 686-702.
14. L. M. Campos, K. L. Killops, R. Sakai, J. M. J. Paulusse, D. Damiron, E. Drockenmuller, B. W. Messmore, C. J. Hawker, Macromolecules 2008, 41, 7063-7070
15. K. L. Killops, L. M. Campos, C. J. Hawker, J. Am. Chem. Soc. 2008, 130, 5062-5064
16. C. E. Hoyle, C. N. Bowman, Angew. Chem. 2010, 122, 1584-1617
17. Angew. Chem. Int. Ed. 2010, 49, 1540-1573
18. C. E. Hoyle, A. B. Lowe, C. N. Bowman, Chem. Soc. Rev. 2010, 39, 1355-1387
19. A. B. Lowe, C. E. Hoyle, C. N. Bowman, J. Mater. Chem. 2010, 20, 4745-4750.
20. C. Brieke, F. Rohrbach, A. Gottschalk, G. Mayer, A. Heckel, Angew. Chem. 2012, 124, 8572-8604
21. Angew. Chem. Int. Ed. 2012, 51, 8446-8476.
22. J. D. Haigh, Nature 1994, 370, 544-546
23. G. Steinberg-Yfrach, J. L. Rigaud, E. N. Durantini, A. L. Moore, D. Gust, T. A. Moore, Nature 1998, 392, 479-482
24. M. H. B. Stowell, T. M. McPhillips, D. C. Rees, S. M. Soltis, E. Abresch, G. Feher, Science 1997, 276, 812-816.
25. P. Brumer, M. Shapiro, Chem. Phys. Lett. 1986, 126, 541-546
26. A. Assion, T. Baumert, M. Bergt, T. Brixner, B. Kiefer, V. Seyfried, M. Strehle, G. Gerber, Science 1998, 282, 919-922.
27. M. L. Wang, K. L. Han, G. Z. He, J. Phys. Chem. A 1998, 102, 10204-10210
28. F. F. Crim, J. Phys. Chem. 1996, 100, 12725-12734.
29. Y. Yagci, S. Jockusch, N. J. Turro, Macromolecules 2010, 43, 6245-6260.
30. Y. Z. Wang, W. J. Song, W. J. Hu, Q. Lin, Angew. Chem. 2009, 121, 5434-5437
31. Angew. Chem. Int. Ed. 2009, 48, 5330-5333
32. S. V. Orski, A. A. Poloukhtine, S. Arumugam, L. D. Mao, V. V. Popik, J. Locklin, J. Am. Chem. Soc. 2010, 132, 11024-11026
33. A. A. Poloukhtine, N. E. Mbua, M. A. Wolfert, G. J. Boons, V. V. Popik, J. Am. Chem. Soc. 2009, 131, 15769-15776.
34. A. Kuzmin, A. Poloukhtine, M. A. Wolfert, V. V. Popik, Bioconjugate Chem. 2010, 21, 2076-2085.
35. V. Kumbaraci, N. Talinli, Y. Yagci, Macromolecules 2006, 39, 6031-6035
36. M. A. Tasdelen, V. Kumbaraci, N. Talinli, Y. Yagci, Polymer 2006, 47, 7611-7614
37. M. A. Tasdelen, V. Kumbaraci, S. Jockusch, N. J. Turro, N. Talinli, Y. Yagci, Macromolecules 2008, 41, 295-297
38. Y. Y. Durmaz, V. Kumbaraci, A. L. Demirel, N. Talinli, Y. Yagci, Macromolecules 2009, 42, 3743-3749
39. V. Kumbaraci, N. Talinli, Y. Yagci, Macromol. Rapid Commun. 2007, 28, 72-77
40. M. A. Tasdelen, V. Kumbaraci, N. Talinli, Y. Yagci, Macromolecules 2007, 40, 4406-4408.
41. S. Arumugam, V. V. Popik, J. Am. Chem. Soc. 2011, 133, 5573-5579.
42. F. Fringuelli, O. Piermatti, F. Pizzo, L. Vaccaro, Eur. J. Org. Chem. 2001, 439-455.
43. A. Chanda, V. V. Fokin, Chem. Rev. 2009, 109, 725-748.
44. R. Huisgen, Pure Appl. Chem. 1980, 52, 2283-2302.
45. S. C. Ritter, B. Koenig, Chem. Commun. 2006, 4694-4696.
46. V. Hong, A. K. Udit, R. A. Evans, M. G. Finn, ChemBioChem 2008, 9, 1481-1486
47. N. K. Devaraj, P. H. Dinolfo, C. E. D. Chidsey, J. P. Collman, J. Am. Chem. Soc. 2006, 128, 1794-1795.
48. L. D. Pachón, J. H. vanMaarseveen, G. Rothenberg, Adv. Synth. Catal. 2005, 347, 811-815
49. G. Molteni, C. L. Bianchi, G. Marinoni, N. Santo, A. Ponti, New J. Chem. 2006, 30, 1137-1139.
50. M. A. Tasdelen, Y. Yagci, Tetrahedron Lett. 2010, 51, 6945-6947
51. M. A. Tasdelen, G. Yilmaz, B. Iskin, Y. Yagci, Macromolecules 2012, 45, 56-61.
52. B. J. Adzima, Y. Tao, C. J. Kloxin, C. A. DeForest, K. S. Anseth, C. N. Bowman, Nat. Chem. 2011, 3, 256-259.
53. R. T. Chen, S. Marchesan, R. A. Evans, K. E. Styan, G. K. Such, A. Postma, K. M. McLean, B. W. Muir, F. Caruso, Biomacromolecules 2012, 13, 889-895.
54. C. Bowman, C.J. Kloxin, B.J. Adzima, (Univ Colorado), WO Patent 074931, 2012.
55. L. Harmand, S. Cadet, B. Kauffmann, L. Scarpantonio, P. Batat, G. Jonusauskas, N. D. McClenaghan, D. Lastecoueres, J.-M. Vincent, Angew. Chem. 2012, 124, 7249-7253
56. Angew. Chem. Int. Ed. 2012, 51, 7137-7141.
57. N. J. Agard, J. A. Prescher, C. R. Bertozzi, J. Am. Chem. Soc. 2004, 126, 15046-15047
58. J. M. Baskin, J. A. Prescher, S. T. Laughlin, N. J. Agard, P. V. Chang, I. A. Miller, A. Lo, J. A. Codelli, C. R. Bertozzi, Proc. Natl. Acad. Sci. USA 2007, 104, 16793-16797.
59. J. S. Clovis, A. Eckell, R. Huisgen, R. Sustmann, Chem. Ber. 1967, 100, 60-70.
60. W. Song, Y. Wang, J. Qu, M. M. Madden, Q. Lin, Angew. Chem. 2008, 120, 2874-2877
61. Angew. Chem. Int. Ed. 2008, 47, 2832-2835
62. W. Song, Y. Wang, J. Qu, Q. Lin, J. Am. Chem. Soc. 2008, 130, 9654-9655.
63. S.-L. Zheng, Y. Wang, Z. Yu, Q. Lin, P. Coppens, J. Am. Chem. Soc. 2009, 131, 18036-18037.
64. M. M. Madden, C. I. R. Vera, W. Song, Q. Lin, Chem. Commun. 2009, 5588-5590
65. Z. Yu, R. K. V. Lim, Q. Lin, Chem. Eur. J. 2010, 16, 13325-13329
66. J. Wang, W. Zhang, W. Song, Y. Wang, Z. Yu, J. Li, M. Wu, L. Wang, J. Zang, Q. Lin, J. Am. Chem. Soc. 2010, 132, 14812-14818.
67. M. Dietrich, G. Delaittre, J. P. Blinco, A. J. Inglis, M. Bruns, C. Barner-Kowollik, Adv. Funct. Mater. 2012, 22, 304-312.
68. Y. Wang, W. J. Hu, W. Song, R. K. V. Lint, Q. Lin, Org. Lett. 2008, 10, 3725-3728
69. Z. Yu, L. Y. Ho, Z. Wang, Q. Lin, Bioorg. Med. Chem. Lett. 2011, 21, 5033-5036
70. Z. Yu, L. Y. Ho, Q. Lin, J. Am. Chem. Soc. 2011, 133, 11912-11915.
71. R. K. V. Lim, Q. Lin, Acc. Chem. Res. 2011, 44, 828-839.
72. R. K. V. Lim, Q. Lin, Chem. Commun. 2010, 46, 7993-7995.
73. S. Arumugam, V. V. Popik, J. Am. Chem. Soc. 2011, 133, 15730-15736
74. S. Arumugam, S. V. Orski, J. Locklin, V. V. Popik, J. Am. Chem. Soc. 2012, 134, 179-182.
75. M. Glassner, K. K. Oehlenschlaeger, T. Gruendling, C. Barner-Kowollik, Macromolecules 2011, 44, 4681-4689
76. M. Winkler, J. O. Mueller, K. K. Oehlenschlaeger, L. M. deEspinosa, M. A. R. Meier, C. Barner-Kowollik, Macromolecules 2012, 45, 5012-5019
77. K. K. Oehlenschlaeger, J. O. Mueller, N. B. Heine, M. Glassner, N. K. Guimard, G. Delaittre, F. G. Schmidt, C. Barner-Kowollik, Angew. Chem. 2013, 125, 791
78. Angew. Chem. Int. Ed. 2013, 52, 762.
79. T. Pauloehrl, G. Delaittre, V. Winkler, A. Welle, M. Bruns, H. G. Boerner, A. M. Greiner, M. Bastmeyer, C. Barner-Kowollik, Angew. Chem. 2012, 124, 1096-1099
80. Angew. Chem. Int. Ed. 2012, 51, 1071-1074.
81. M. Uygun, M. A. Tasdelen, Y. Yagci, Macromol. Chem. Phys. 2010, 211, 103-110
82. A. Dondoni, A. Marra, Chem. Soc. Rev. 2012, 41, 573-586
83. A. B. Lowe, Polym. Chem. 2010, 1, 17-36
84. C. E. Hoyle, T. Y. Lee, T. Roper, J. Polym. Sci. Part A 2004, 42, 5301-5338.
85. S. Arumugam, V. V. Popik, J. Am. Chem. Soc. 2012, 134, 8408-8411.
86. K. L. Christman, R. M. Broyer, Z. P. Tolstyka, H. D. Maynard, J. Mater. Chem. 2007, 17, 2021-2027
87. S. Park, M. N. Yousaf, Langmuir 2008, 24, 6201-6207.
88. T. Pauloehrl, G. Delaittre, M. Bruns, M. Meißler, H. G. Börner, M. Bastmeyer, C. Barner-Kowollik, Angew. Chem. 2012, 124, 9316-9319
89. Angew. Chem. Int. Ed. 2012, 51, 9181-9184.
90. F. A. Leibfarth, Y. Schneider, N. A. Lynd, A. Schultz, B. Moon, E. J. Kramer, G. C. Bazan, C. J. Hawker, J. Am. Chem. Soc. 2010, 132, 14706-14709
91. M. Wolffs, M. J. Kade, C. J. Hawker, Chem. Commun. 2011, 47, 10572-10574.
92. O. Soltani, J. K. DeBrabander, Angew. Chem. 2005, 117, 1724-1727
93. Angew. Chem. Int. Ed. 2005, 44, 1696-1699
94. V. Kumbaraci, B. Aydogan, N. Talinli, Y. Yagci, J. Polym. Sci. Part A 2012, 50, 2612-2618
95. G. Yilmaz, V. Kumbaraci, N. Talinli, P. Tatar, A. L. Demirel, Y. Yagci, J. Polym. Sci. Part A 2012, 50, 2517-2520.
96. M. Yan, Chem. Eur. J. 2007, 13, 4138-4144
97. S. A. Al-Bataineh, R. Luginbuehl, M. Textor, M. Yan, Langmuir 2009, 25, 7432-7437
98. L.-H. Liu, H. Dietsch, P. Schurtenberger, M. Yan, Bioconjugate Chem. 2009, 20, 1349-1355
99. J. P. Gann, M. Yan, Langmuir 2008, 24, 5319-5323
100. X. Wang, O. Ramstrom, M. Yan, J. Mater. Chem. 2009, 19, 8944-8949.
101. L.-H. Liu, M. Yan, Acc. Chem. Res. 2010, 43, 1434-1443.
102. M. D. Yan, J. Ren, Chem. Mater. 2004, 16, 1627-1632
103. L. Liu, M. H. Engelhard, M. Yan, J. Am. Chem. Soc. 2006, 128, 14067-14072.
104. M. D. Yan, J. Ren, J. Mater. Chem. 2005, 15, 523-527
105. H. Wang, L. Li, Q. Tong, M. Yan, ACS Appl. Mater. Interfaces 2011, 3, 3463-3471.
106. Y. Pei, H. Yu, Z. Pei, M. Theurer, C. Ammer, S. Andre, H.-J. Gabius, M. Yan, O. Ramstroem, Anal. Chem. 2007, 79, 6897-6902.
107. T. Kubo, X. Wang, Q. Tong, M. Yan, Langmuir 2011, 27, 9372-9378.
108. M. Conradi, T. Junkers, Macromolecules 2011, 44, 7969-7976.