Organic donor-acceptor assemblies form coaxial p-n heterojunctions with high photoconductivity

Angewandte Chemie - International Edition

Volumn 54, Issue 3, 2015, Pages 946-950

  Prasanthkumar, Seelam ^a   Ghosh, Samrat ^a   Nair, Vijayakumar C ^a   Saeki, Akinori ^b   Seki, Shu ^b   Ajayaghosh, Ayyappanpillai ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

Donor acceptor systems; p n heterojunctions; Photoconductivity; Self assembly; Self sorting

Indexed keywords

ABSORPTION SPECTROSCOPY; ATOMIC FORCE MICROSCOPY; MOLECULES; PHOTOCONDUCTIVITY; PHOTOLYSIS; SELF ASSEMBLY; X RAY DIFFRACTION;

DONOR-ACCEPTOR SYSTEM; KELVIN PROBE FORCE MICROSCOPY; N-TYPE SEMICONDUCTORS; P-N HETEROJUNCTIONS; PHOTOCURRENT GENERATIONS; POWDER X RAY DIFFRACTION; SELF-SORTING; TIME-RESOLVED MICROWAVE CONDUCTIVITIES;

HETEROJUNCTIONS;

EID: 84920837154     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201408831     Document Type: Article

References (82)

1. a) T. Aida, E. W. Meijer, S. I. Stupp, Science 2012, 335, 813-817;
2. b) F. S. Kim, G. Q. Ren, S. A. Jenekhe, Chem. Mater. 2011, 23, 682-732;
3. c) L. C. Palmer, S. I. Stupp, Acc. Chem. Res. 2008, 41, 1674-1684;
4. d) J. D. Hartgerink, E. Beniash, S. I. Stupp, Science 2001, 294, 1684-1688;
5. e) F. J. M. Hoeben, P. Jonkheijm, E. W. Meijer, A. P. H. J. Schenning, Chem. Rev. 2005, 105, 1491-1546;
6. f) A. P. Alivisatos, Science 1996, 271, 933-937.
7. a) A. Mishra, P. Bäuerle, Angew. Chem. Int. Ed. 2012, 51, 2020-2067;
8. Angew. Chem. 2012, 124, 2060-2109;
9. b) G. Li, R. Zhu, Y. Yang, Nat. Photonics 2012, 6, 153-161;
10. c) N. S. Dang, L. Hirsch, G. Wantz, J. D. Wuest, Chem. Rev. 2013, 113, 3734-3765;
11. d) Y. Lin, Y. Li, X. Zhan, Chem. Soc. Rev. 2012, 41, 4245-4272.
12. a) J. J. M. Halls, C. A. Walsh, N. C. Greenham, E. A. Marseglia, R. H. Friend, S. C. Moratti, A. B. Holmes, Nature 1995, 376, 498-500;
13. b) G. Yu, J. Gao, J. C. Hummelen, F. Wudl, A. J. Heeger, Science 1995, 270, 1789-1791;
14. c) P. Peumans, S. Uchida, S. R. Forrest, Nature 2003, 425, 158-162;
15. d) J. Y. Kim, K. Lee, N. E. Coates, D. Moses, T. Q. Nguyen, M. Dante, A. J. Heeger, Science 2007, 317, 222-225;
16. e) L. Dong, W. Li, W.-S. Li, Nanoscale 2011, 3, 3447-3461.
17. a) J. M. Lehn, Supramolecular Chemistry: Concepts and Perspectives, Wiley, New York, 1995, pp. 139-198;
18. b) M. M. Safont-Sempere, G. Fernández, F. Würthner, Chem. Rev. 2011, 111, 5784-5814;
19. c) A. Das, S. Ghosh, Angew. Chem. Int. Ed. 2014, 53, 2038-2054;
20. Angew. Chem. 2014, 126, 2068-2084;
21. d) S. S. Babu, S. Prasanthkumar, A. Ajayaghosh, Angew. Chem. Int. Ed. 2012, 51, 1766-1776;
22. Angew. Chem. 2012, 124, 1800-1810.
23. a) W. Zhang, W. Jin, T. Fukushima, A. Saeki, S. Seki, T. Aida, Science 2011, 334, 340-343;
24. b) R. Bhosale, J. Misek, N. Sakai, S. Matile, Chem. Soc. Rev. 2010, 39, 138-149;
25. c) J. van Herrikhuyzen, A. Syamakumari, A. P. H. J. Schenning, E. W. Meijer, J. Am. Chem. Soc. 2004, 126, 10021-10027;
26. d) D. M. Bassani, L. Jonusauskaite, A. Lavie-Cambot, N. D. McClenaghan, J. L. Pozzo, D. Ray, G. Vives, Coord. Chem. Rev. 2010, 254, 2429-2445.
27. a) F. Würthner, Z. Chen, F. J. M. Hoeben, P. Osswald, C. C. You, P. Jonkheijm, J. van Herrikhuyzen, A. P. H. J. Schenning, P. P. A. M. van der Schoot, E. W. Meijer, E. H. A. Beckers, S. C. J. Meskers, R. A. J. Janssen, J. Am. Chem. Soc. 2004, 126, 10611-10618;
28. b) H. Huang, C. E. Chou, Y. Che, L. Li, C. Wang, X. Yang, Z. Peng, L. Zang, J. Am. Chem. Soc. 2013, 135, 16490-16496;
29. c) L. Bu, E. Pentzer, F. A. Bokel, T. Emrick, R. C. Hayward, ACS Nano 2012, 6, 10924-10929;
30. d) M. Brinkmann, E. Gonthier, S. Bogen, K. Tremel, S. Ludwigs, M. Hufnagel, M. Sommer, ACS Nano 2012, 6, 10319-10326.
31. a) A. Ajayaghosh, V. K. Praveen, Acc. Chem. Res. 2007, 40, 644-656;
32. b) A. Ajayaghosh, V. K. Praveen, C. Vijayakumar, Chem. Soc. Rev. 2008, 37, 109-122;
33. c) V. K. Praveen, C. Ranjith, E. Bandini, A. Ajayaghosh, N. Armaroli, Chem. Soc. Rev. 2014, 43, 4222-4242;
34. d) K. K. Kartha, R. D. Mukhopadhyay, A. Ajayaghosh, Chimia 2013, 67, 51-63;
35. e) S. S. Babu, V. K. Praveen, A. Ajayaghosh, Chem. Rev. 2014, 114, 1973-2129;
36. f) M. R. Molla, A. Das, S. Ghosh, Chem. Eur. J. 2010, 16, 10084-10093;
37. g) E. Busseron, Y. Ruff, E. Moulin, N. Giuseppone, Nanoscale 2013, 5, 7098-7140.
38. a) A. Ajayaghosh, S. J. George, V. K. Praveen, Angew. Chem. Int. Ed. 2003, 42, 332-335;
39. Angew. Chem. 2003, 115, 346-349;
40. b) V. K. Praveen, S. J. George, R. Varghese, C. Vijayakumar, A. Ajayaghosh, J. Am. Chem. Soc. 2006, 128, 7542-7550;
41. c) A. Ajayaghosh, V. K. Praveen, S. Srinivasan, R. Varghese, Adv. Mater. 2007, 19, 411-415;
42. d) C. Vijayakumar, V. K. Praveen, A. Ajayaghosh, Adv. Mater. 2009, 21, 2059-2063;
43. e) S. S. Babu, K. K. Kartha, A. Ajayaghosh, J. Phys. Chem. Lett. 2010, 1, 3413-3424;
44. f) F. García, J. Buendìa, S. Ghosh, A. Ajayaghosh, L. Sánchez, Chem. Commun. 2013, 49, 9278-9280;
45. g) S. Santhosh Babu, J. Aimi, H. Ozawa, N. Shirahata, A. Saeki, S. Seki, A. Ajayaghosh, H. Möhwald, T. Nakanishi, Angew. Chem. Int. Ed. 2012, 51, 3391-3395;
46. Angew. Chem. 2012, 124, 3447-3451.
47. a) K. P. Goetz, D. Vermeulen, M. E. Payne, C. Kloc, L. E. McNeil, O. D. Jurchescu, J. Mater. Chem. C 2014, 2, 3065-3076;
48. b) K. Jalani, M. Kumar, S. J. George, Chem. Commun. 2013, 49, 5174-5176;
49. c) P. Jonkheijm, N. Stutzmann, Z. Chen, D. M. de Leeuw, E. W. Meijer, A. P. H. J. Schenning, F. Würthner, J. Am. Chem. Soc. 2006, 128, 9535-9540;
50. d) L. F. Dössel, V. Kamm, I. A. Howard, F. Laquai, W. Pisula, X. Feng, C. Li, M. Takase, T. Kudernac, S. De Feyter, K. Müllen, J. Am. Chem. Soc. 2012, 134, 5876-5886.
51. a) K. Sugiyasu, S. I. Kawano, N. Fujita, S. Shinkai, Chem. Mater. 2008, 20, 2863-2865;
52. b) A. Wicklein, S. Ghosh, M. Sommer, F. Würthner, M. Thelakkat, ACS Nano 2009, 3, 1107-1114.
53. a) S. Prasanthkumar, A. Saeki, S. Seki, A. Ajayaghosh, J. Am. Chem. Soc. 2010, 132, 8866-8867;
54. b) S. Prasanthkumar, A. Gopal, A. Ajayaghosh, J. Am. Chem. Soc. 2010, 132, 13206-13207.
55. a) D. Görl, X. Zhang, F. Würthner, Angew. Chem. Int. Ed. 2012, 51, 6328-6348;
56. Angew. Chem. 2012, 124, 6434-6455;
57. b) F. Würthner, Chem. Commun. 2004, 1564-1579;
58. c) T. E. Kaiser, H. Wang, V. Stepanenko, F. Würthner, Angew. Chem. Int. Ed. 2007, 46, 5541-5544;
59. Angew. Chem. 2007, 119, 5637-5640.
60. a) Y. Wen, Y. Liu, Adv. Mater. 2010, 22, 1331-1345;
61. b) X. Zhan, Z. Tan, B. Domercq, Z. An, X. Zhang, S. Barlow, Y. Li, D. Zhu, B. Kippelen, S. R. Marder, J. Am. Chem. Soc. 2007, 129, 7246-7247.
62. K. Balakrishnan, A. Datar, T. Naddo, J. Huang, R. Oitker, M. Yen, J. Zhao, L. Zang, J. Am. Chem. Soc. 2006, 128, 7390-7398.
63. a) F. C. Spano, Acc. Chem. Res. 2009, 42, 429-439;
64. b) A. Ajayaghosh, C. Vijayakumar, R. Varghese, S. J. George, Angew. Chem. Int. Ed. 2006, 45, 456-460;
65. Angew. Chem. 2006, 118, 470-474;
66. c) U. Rösch, S. Yao, R. Wortmann, F. Würthner, Angew. Chem. Int. Ed. 2006, 45, 7026-7030;
67. Angew. Chem. 2006, 118, 7184-7188.
68. F. Würthner, T. E. Kaiser, C. R. Saha-Möller, Angew. Chem. Int. Ed. 2011, 50, 3376-3410;
69. Angew. Chem. 2011, 123, 3436-3473.
70. a) A. Liscio, V. Palermo, P. Samorì, Adv. Funct. Mater. 2008, 18, 907-914;
71. b) A. Liscio, V. Palermo, P. Samorì, Acc. Chem. Res. 2010, 43, 541-550;
72. c) A. Liscio, G. De Luca, F. Nolde, V. Palermo, K. Müllen, P. Samorì, J. Am. Chem. Soc. 2008, 130, 780-781;
73. d) V. Palermo, M. B. J. Otten, A. Liscio, E. Schwartz, P. A. J. de Witte, M. A. Castriciano, M. M. Wienk, F. Nolde, G. De Luca, J. J. L. M. Cornelissen, R. A. J. Janssen, K. Müllen, A. E. Rowan, R. J. M. Nolte, P. Samorì, J. Am. Chem. Soc. 2008, 130, 14605-14614;
74. e) F. Fuchs, M. Linares, C. de Vet, P. Leclère, R. Demadrille, B. Grévin, Adv. Mater. 2014, 26, 6416-6422.
75. a) A. Saeki, S. Seki, T. Takenobu, Y. Iwasa, S. Tagawa, Adv. Mater. 2008, 20, 920-923;
76. b) A. Saeki, S.-i. Ohsaki, S. Seki, S. Tagawa, J. Phys. Chem. C 2008, 112, 16643-16650;
77. c) Y. He, Y. Yamamoto, W. Jin, T. Fukushima, A. Saeki, S. Seki, N. Ishii, T. Aida, Adv. Mater. 2010, 22, 829-832;
78. d) A. Saeki, Y. Koizumi, T. Aida, S. Seki, Acc. Chem. Res. 2012, 45, 1193-1202.
79. a) A. Saeki, M. Tsuji, S. Seki, Adv. Energy Mater. 2011, 1, 661-669;
80. b) A. Saeki, S. Yoshikawa, M. Tsuji, Y. Koizumi, M. Ide, C. Vijayakumar, S. Seki, J. Am. Chem. Soc. 2012, 134, 19035-19042;
81. c) B. Balan, C. Vijayakumar, A. Saeki, Y. Koizumi, M. Tsujia, S. Seki, Polym. Chem. 2013, 4, 2293-2303;
82. d) W. A. Braunecker, S. D. Oosterhout, Z. R. Owczarczyk, R. E. Larsen, B. W. Larson, D. S. Ginley, O. V. Boltalina, S. H. Strauss, N. Kopidakis, D. C. Olson, Macromolecules 2013, 46, 3367-3375.