Structural Design Principle of Small-Molecule Organic Semiconductors for Metal-Free, Visible-Light-Promoted Photocatalysis

Angewandte Chemie - International Edition

Volumn 55, Issue 33, 2016, Pages 9783-9787

  Wang, Lei ^a   Huang, Wei ^a   Li, Run ^a   Gehrig, Dominik ^a   Blom, Paul W M ^a   Landfester, Katharina ^a   Zhang, Kai A I ^a  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

Author keywords

C H functionalization; metal free catalysts; photocatalysis; small molecule organic semiconductor; visible light

Indexed keywords

BAND STRUCTURE; ELECTRON TRANSPORT PROPERTIES; METALS; MOLECULES; ORGANIC SEMICONDUCTOR MATERIALS; PHOTOCATALYSIS; PHOTOCATALYTIC ACTIVITY; STRUCTURAL DESIGN; SYNTHESIS (CHEMICAL);

FUNCTIONALIZATIONS; MECHANISTIC STUDIES; METAL-FREE CATALYSTS; PHOTOGENERATED EXCITONS; SEMICONDUCTOR MOLECULES; SMALL-MOLECULE ORGANIC SEMICONDUCTOR; VISIBLE LIGHT; VISIBLE LIGHT ACTIVE PHOTOCATALYSTS;

LIGHT;

EID: 84978961891     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201603789     Document Type: Article

References (65)

1. D. Ravelli, M. Fagnoni, A. Albini, Chem. Soc. Rev. 2013, 42, 97–113;
2. K. Zeitler, Angew. Chem. Int. Ed. 2009, 48, 9785–9789;
3. Angew. Chem. 2009, 121, 9969–9974;
4. J. Xuan, W. J. Xiao, Angew. Chem. Int. Ed. 2012, 51, 6828–6838;
5. Angew. Chem. 2012, 124, 6934–6944;
6. J. M. R. Narayanam, C. R. J. Stephenson, Chem. Soc. Rev. 2011, 40, 102–113;
7. C. K. Prier, D. A. Rankic, D. W. C. MacMillan, Chem. Rev. 2013, 113, 5322–5363;
8. D. A. Nicewicz, D. W. C. MacMillan, Science 2008, 322, 77–80;
9. J. M. R. Narayanam, J. W. Tucker, C. R. J. Stephenson, J. Am. Chem. Soc. 2009, 131, 8756.
10. S. Ventre, F. R. Petronijevic, D. W. C. MacMillan, J. Am. Chem. Soc. 2015, 137, 5654–5657;
11. J. D. Cuthbertson, D. W. C. MacMillan, Nature 2015, 519, 74–77;
12. E. L. Tyson, M. S. Ament, T. P. Yoon, J. Org. Chem. 2013, 78, 2046–2050;
13. L. R. Espelt, I. S. McPherson, E. M. Wiensch, T. P. Yoon, J. Am. Chem. Soc. 2015, 137, 2452–2455;
14. J. D. Nguyen, E. M. D′Amato, J. M. R. Narayanam, C. R. J. Stephenson, Nat. Chem. 2012, 4, 854–859;
15. C. J. Yao, Q. Sun, N. Rastogi, B. Konig, ACS Catal. 2015, 5, 2935–2938;
16. E. Brachet, T. Ghosh, I. Ghosh, B. Konig, Chem. Sci. 2015, 6, 987–992;
17. R. Brimioulle, D. Lenhart, M. M. Maturi, T. Bach, Angew. Chem. Int. Ed. 2015, 54, 3872–3890;
18. Angew. Chem. 2015, 127, 3944–3963.
19. Q. M. Kainz, C. D. Matier, A. Bartoszewicz, S. L. Zultanski, J. C. Peters, G. C. Fu, Science 2016, 351, 681–684;
20. S. Paria, O. Reiser, ChemCatChem 2014, 6, 2477–2483.
21. S. P. Pitre, C. D. McTiernan, H. Ismaili, J. C. Scaiano, ACS Catal. 2014, 4, 2530–2535;
22. M. Neumann, S. Fuldner, B. Konig, K. Zeitler, Angew. Chem. Int. Ed. 2011, 50, 951–954;
23. Angew. Chem. 2011, 123, 981–985;
24. K. Ohkubo, K. Mizushima, R. Iwata, K. Souma, N. Suzuki, S. Fukuzumi, Chem. Commun. 2010, 46, 601–603;
25. S. P. Pitre, C. D. McTiernan, H. Ismaili, J. C. Scaiano, J. Am. Chem. Soc. 2013, 135, 13286–13289;
26. K. Ohkubo, T. Kobayashi, S. Fukuzumi, Angew. Chem. Int. Ed. 2011, 50, 8652–8655;
27. Angew. Chem. 2011, 123, 8811–8814;
28. D. P. Hari, P. Schroll, B. Konig, J. Am. Chem. Soc. 2012, 134, 2958–2961;
29. D. J. Wilger, N. J. Gesmundo, D. A. Nicewicz, Chem. Sci. 2013, 4, 3160–3165.
30. Y. Lin, Y. Li, X. Zhan, Chem. Soc. Rev. 2012, 41, 4245–4272;
31. A. Mishra, P. Bäuerle, Angew. Chem. Int. Ed. 2012, 51, 2020–2067;
32. Angew. Chem. 2012, 124, 2060–2109.
33. F. Su, S. C. Mathew, G. Lipner, X. Fu, M. Antonietti, S. Blechert, X. Wang, J. Am. Chem. Soc. 2010, 132, 16299–16301;
34. F. Su, S. C. Mathew, L. Möhlmann, M. Antonietti, X. Wang, S. Blechert, Angew. Chem. Int. Ed. 2011, 50, 657–660;
35. Angew. Chem. 2011, 123, 683–686;
36. X. Wang, S. Blechert, M. Antonietti, ACS Catal. 2012, 2, 1596–1606;
37. F. Vilela, K. Zhang, M. Antonietti, Energy Environ. Sci. 2012, 5, 7819–7832;
38. K. Zhang, D. Kopetzki, P. H. Seeberger, M. Antonietti, F. Vilela, Angew. Chem. Int. Ed. 2013, 52, 1432–1436;
39. Angew. Chem. 2013, 125, 1472–1476;
40. N. Kang, J. H. Park, K. C. Ko, J. Chun, E. Kim, H. W. Shin, S. M. Lee, H. J. Kim, T. K. Ahn, J. Y. Lee, S. U. Son, Angew. Chem. Int. Ed. 2013, 52, 6228–6232;
41. Angew. Chem. 2013, 125, 6348–6352;
42. K. Zhang, Z. Vobecka, K. Tauer, M. Antonietti, F. Vilela, Chem. Commun. 2013, 49, 11158–11160;
43. S. Ghasimi, S. Prescher, Z. J. Wang, K. Landfester, J. Yuan, K. A. I. Zhang, Angew. Chem. Int. Ed. 2015, 54, 14549–14553;
44. Angew. Chem. 2015, 127, 14757–14761;
45. M. Baar, S. Blechert, Chem. Eur. J. 2015, 21, 526–530.
46. X. Wang, K. Maeda, A. Thomas, K. Takanabe, G. Xin, J. M. Carlsson, K. Domen, M. Antonietti, Nat. Mater. 2009, 8, 76–80;
47. J. Zhang, G. Zhang, X. Chen, S. Lin, L. Mohlmann, G. Dolega, G. Lipner, M. Antonietti, S. Blechert, X. Wang, Angew. Chem. Int. Ed. 2012, 51, 3183–3187;
48. Angew. Chem. 2012, 124, 3237–3241;
49. Y. Wang, X. Wang, M. Antonietti, Angew. Chem. Int. Ed. 2012, 51, 68;
50. Angew. Chem. 2012, 124, 70;
51. R. S. Sprick, J.-X. Jiang, B. Bonillo, S. Ren, T. Ratvijitvech, P. Guiglion, M. A. Zwijnenburg, D. J. Adams, A. I. Cooper, J. Am. Chem. Soc. 2015, 137, 3265–3270;
52. Y. Zheng, L. Lin, B. Wang, X. Wang, Angew. Chem. Int. Ed. 2015, 54, 12868–12884;
53. Angew. Chem. 2015, 127, 13060–13077;
54. R. S. Sprick, B. Bonillo, R. Clowes, P. Guiglion, N. J. Brownbill, B. J. Slater, F. Blanc, M. A. Zwijnenburg, D. J. Adams, A. I. Cooper, Angew. Chem. Int. Ed. 2016, 55, 1792–1796;
55. Angew. Chem. 2016, 128, 1824–1828.
56. I. Ghosh, T. Ghosh, J. I. Bardagi, B. König, Science 2014, 346, 725–728;
57. C. D. McTiernan, S. P. Pitre, J. C. Scaiano, ACS Catal. 2014, 4, 4034–4039.
58. V. Coropceanu, J. Cornil, D. A. da Silva Filho, Y. Olivier, R. Silbey, J.-L. Brédas, Chem. Rev. 2007, 107, 926–952.
59. J.-L. Bredas, Mater. Horiz. 2014, 1, 17–19.
60. L. Furst, B. S. Matsuura, J. M. R. Narayanam, J. W. Tucker, C. R. J. Stephenson, Org. Lett. 2010, 12, 3104–3107.
61. Z. J. Wang, S. Ghasimi, K. Landfester, K. A. I. Zhang, Adv. Mater. 2015, 27, 6265–6270;
62. R. Li, Z. J. Wang, L. Wang, B. C. Ma, S. Ghasimi, H. Lu, K. Landfester, K. A. I. Zhang, ACS Catal. 2016, 6, 1113–1121.
63. See Ref. [11].
64. D. A. Nagib, D. W. C. MacMillan, Nature 2011, 480, 224–228.
65. M. Belletete, L. Mazerolle, N. Desrosiers, M. Leclerc, G. Durocher, Macromolecules 1995, 28, 8587–8597.