Ultrathin n-type organic nanoribbons with high photoconductivity and application in optoelectronic vapor sensing of explosives

Journal of the American Chemical Society

Volumn 132, Issue 16, 2010, Pages 5743-5750

  Che, Yanke ^a   Yang, Xiaomei ^a   Liu, Guilin ^b   Yu, Chun ^b   Ji, Hongwei ^b   Zuo, Jianmin ^c   Zhao, Jincai ^b   Zang, Ling ^a  

^a UNIVERSITY OF UTAH   (United States)

^b INSTITUTE OF CHEMISTRY   (China)

^c UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADSORBED OXYGEN; AMPHIPHILICS; CHARGE TRANSPORT; CHEMIRESISTORS; ELECTRICAL CONDUCTIVITY; ELECTRON DONOR ACCEPTORS; INTERMOLECULAR ASSEMBLY; INTRAMOLECULAR CHARGE; KINETIC BALANCE; LARGE SURFACE AREA; LIGHT TURNING; MOLECULAR DESIGN; N-TYPE SEMICONDUCTORS; NANOPOROSITY; NANORIBBONS; NITRO-BASED EXPLOSIVES; OXIDIZING SPECIES; PERYLENE TETRACARBOXYLIC DIIMIDE; PHOTOCONDUCTION; PHOTOGENERATED ELECTRONS; SUPRAMOLECULES; ULTRA-THIN; UNIQUE FEATURES; VAPOR SENSING; WHITE LIGHT;

CHARGE CARRIERS; OXYGEN; VAPORS;

PHOTOCONDUCTIVITY;

AMPHOPHILE; EXPLOSIVE; GLYCERYL TRINITRATE; NANORIBBON; OXIDIZING AGENT; OXYGEN; PERYLENE; PERYLENE TETRACARBOXYLIC DIIMIDE; UNCLASSIFIED DRUG;

ADSORPTION; ARTICLE; CONDUCTANCE; CONTROLLED STUDY; ELECTRIC CONDUCTIVITY; ELECTRON; FIBER; FILM; ILLUMINATION; KINETICS; MOLECULE; MORPHOLOGY; NANOPORE; OPTOELECTRONIC VAPOR SENSING; PHOTOCONDUCTION; POROSITY; REPRODUCIBILITY; SEMICONDUCTOR; SENSOR; SURFACE PROPERTY; SYNTHESIS; VAPOR; WHITE LIGHT;

EID: 77952573030     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja909797q     Document Type: Article

References (55)

1. Hoeben, F. J. M., Jonkheijm, P., Meijer, E. W., and Schenning, A. P. H. J. Chem. Rev. 2005, 105, 1491-1546
2. Xia, Y., Yang, P., Sun, Y., Wu, Y., Mayers, B., Gates, B., Yin, Y., Kim, F., and Yan, H. Adv. Mater. 2003, 15, 353-389
3. Hu, J., Odom, T. W., and Lieber, C. M. Acc. Chem. Res. 1999, 32, 435-445
4. Zang, L., Che, Y., and Moore, J. S. Acc. Chem. Res. 2008, 41, 1596-1608
5. Zhao, Y. S., Fu, H., Peng, A., Ma, Y., Xiao, D., and Yao, J. Adv. Mater. 2008, 20, 2859-2876
6. Wang, J., Gudiksen, M. S., Duan, X., Cui, Y., and Lieber, C. M. Science 2001, 293, 1455-1457
7. Kind, H., Yan, H., Messer, B., Law, M., and Yang, P. Adv. Mater. 2002, 14, 158-60
8. Ahn, Y., Dunning, J., and Park, J. Nano Lett. 2005, 5, 1367-1370
9. OBrien, G. A., Quinn, A. J., Tanner, D. A., and Redmond, G. Adv. Mater. 2006, 18, 2379-2383
10. Yamamoto, Y., Fukushima, T., Suna, Y., Ishii, N., Saeki, A., Seki, S., Tagawa, S., Taniguchi, M., Kawai, T., and Aida, T. Science 2006, 314, 1761-1764
11. Schwab, A. D., Smith, D. E., Bond-Watts, B., Johnston, D. E., Hone, J., Johnson, A. T., dePaula, J. C., and Smith, W. F. Nano Lett. 2004, 4, 1261-1265
12. Jiang, L., Fu, Y., Li, H., and Hu, W. J. Am. Chem. Soc. 2008, 130, 3937
13. Zhang, Y., Chen, P., Jiang, L., Hu, W., and Liu, M. J. Am. Chem. Soc. 2009, 131, 2756-2757
14. Gong, J., Li, Y., Chai, X., Hu, Z., and Deng, Y. J. Phys. Chem. C 114, 1293-1298
15. Lao, C., Li, Y., Wong, C. P., and Wang, Z. L. Nano Lett. 2007, 7, 1323-1328
16. Wang, D., Hao, C., Zheng, W., Peng, Q., Wang, T., Liao, Z., Yu, D., and Li, Y. Adv. Mater. 2008, 20, 2628-2632
17. Freitag, M., Martin, Y., Misewich, J. A., Martel, R., and Avouris, P. Nano Lett. 2003, 3, 1067-71
18. Zhang, X., Jie, J., Zhang, W., Zhang, C., Luo, L., He, Z., Zhang, X., Zhang, W., Lee, C., and Lee, S. Adv. Mater. 2008, 20, 2427-2432
19. Newman, C. R., Frisbie, C. D., da Silva Filho, D. A., Bredas, J.-L., Ewbank, P. C., and Mann, K. R. Chem. Mater. 2004, 16, 4436-4451
20. Jones, B. A., Facchetti, A., Wasielewski, M. R., and Marks, T. J. J. Am. Chem. Soc. 2007, 129, 15259-15278
21. Pisula, W., Kastler, M., Wasserfallen, D., Robertson Joseph, W. F., Nolde, F., Kohl, C., and Mullen, K. Angew. Chem., Int. Ed. 2006, 45, 819-23
22. Percec, V., Glodde, M., Bera, T. k., Miura, Y., Shiyanovsaya, I., Singer, K. D., Balagurusamy, V. S. K., Helney, P. A., Schnell, I., Rapp, A., Spiess, H. W., Hudson, S. D., and Duan, H. Nature 2002, 417, 384-387
23. Kishore, R. S. K., Kel, O., Banerji, N., Emery, D., Bollot, G., Mareda, J., Gomez-Casado, A., Jonkheijm, P., Huskens, J., Maroni, P., Borkovec, M., Vauthey, E., Sakai, N., and Matile, S. J. Am. Chem. Soc. 2009, 131, 11106-11116
24. Wurthner, F. Chem. Commun. 2004, 1564-79
25. Schenning, A. P. H. J., Herrikhuyzen, J. V., Jonkheijm, P., Chen, Z., Wurthner, F., and Meijer, E. W. J. Am. Chem. Soc. 2002, 124, 10252-10253
26. Wurthner, F., Chen, Z., Hoeben, F. J. M., Osswald, P., You, C. C., Jonkheijm, P., Herrikhuyzen, J. v., Schenning, A. P. H. J., vanderSchoot, P. P. A. M., Meijer, E. W., Beckers, E. H. A., Meskers, S. C. J., and Janssen, R. A. J. J. Am. Chem. Soc. 2004, 126, 10611-10618
27. Beckers, E. H. A., Meskers, S. C. J., Schenning, A. P. H. J., Chen, Z., Wurthner, F., Marsal, P., Beljonne, D., Cornil, J., and Janssen, R. A. J. J. Am. Chem. Soc. 2005, 128, 649
28. Bullock, J. E., Carmieli, R., Mickley, S. M., Vura-Weis, J., and Wasielewski, M. R. J. Am. Chem. Soc. 2009, 131, 11919
29. Kelley, R. F., Shin, W. S., Rybtchinski, B., Sinks, L. E., and Wasielewski, M. R. J. Am. Chem. Soc. 2007, 129, 3173
30. Xie, D., Jiang, Y., Pan, W., Jiang, J., Wu, Z., and Li, Y. Thin Solid Films 2002, 406, 262-267
31. Antonisse, M. M. G., Snellink-Ruel, B. H. M., Yigit, I., Engbersen, J. F. J., and Reinhoudt, D. N. J. Org. Chem. 1997, 62, 9034
32. Kazmaier, P. M. and Hoffmann, R. J. Am. Chem. Soc. 1994, 116, 9684-91
33. Zang, L., Liu, R., Holman, M. W., Nguyen, K. T., and Adams, D. M. J. Am. Chem. Soc. 2002, 124, 10640-10641
34. Langhals, H. Heterocycles 1995, 40, 477-500
35. Che, Y., Datar, A., Balakrishnan, K., and Zang, L. J. Am. Chem. Soc. 2007, 129, 7234-7235
36. Palmer, L. C. and Stupp, S. I. Acc. Chem. Res. 2008, 41, 1674
37. Zubarev, E. R., Sone, E. D., and Stupp, S. I. Chem.-Eur. J. 2006, 12, 7313-7327
38. Bushey, M. L., Hwang, A., Stephens, P. W., and Nuckolls, C. J. Am. Chem. Soc. 2001, 123, 8157-8
39. Che, Y., Yang, X., Loser, S., and Zang, L. Nano Lett. 2008, 8, 2219-2223
40. Zhang, X., Chen, Z., and Wurthner, F. J. Am. Chem. Soc. 2007, 129, 4886-4887
41. Yang, W.-Y., Lee, E., and Lee, M. J. Am. Chem. Soc. 2006, 128, 3484
42. Crispin, X., Cornil, J., Friedlein, R., Okudaira, K. K., Lemaur, V., Crispin, A., Kestemont, G., Lehmann, M., Fahlman, M., Lazzaroni, R., Geerts, Y., Wendin, G., Ueno, N., Bredas, J.-L., and Salaneck, W. R. J. Am. Chem. Soc. 2004, 126, 11889-11899
43. Cohen, Y. S., Xiao, S., Steigerwald, M. L., Nuckolls, C., and Kagan, C. R. Nano Lett. 2006, 6, 2838-2841
44. Rochefort, A., Martel, R., and Avouris, P. Nano Lett. 2002, 2, 877-880
45. Sofos, M., Goldberger, J., Stone, D. A., Allen, J. E., Ma, Q., Herman, D. J., Tsai, W.-W., Lauhon, L. J., and Stupp, S. I. Nat. Mater. 2009, 8, 68-75
46. Messmore, B. W., Hulvat, J. F., Sone, E. D., and Stupp, S. I. J. Am. Chem. Soc. 2004, 126, 14452
47. Due to the negligible conductivity of the materials in the dark, depositing more materials within the two-electrode junction will bring little change to the dark current. However, the photocurrent will increase proportionally with the amount of materials deposited. Therefore, the longer the electrode used, the more materials incorporated, and thus the higher the on/off ratio obtained, as previously practiced by Aida et al. (10)
48. Adams, D. M. J. Phys. Chem. B 2003, 107, 6668-6697
49. Xu, B. Q. and Tao, N. J. Science 2003, 301, 1221-1223
50. Naddo, T., Che, Y., Zhang, W., Balakrishnan, K., Yang, X., Yen, M., Zhao, J., Moore, J. S., and Zang, L. J. Am. Chem. Soc. 2007, 129, 6978-6979
51. Che, Y. and Zang, L. Chem. Commun. 2009, 5106-5108
52. Naddo, T., Yang, X., Moore, J. S., and Zang, L. Sens. Actuators, B 2008, B134, 287-291
53. Yang, J.-S. and Swager, T. M. J. Am. Chem. Soc. 1998, 120, 11864-11873
54. DHS Science & Technology Directorate Explosives Division: http://www.dhs.gov/xabout/structure/gc-1224522488810.shtm.
55. Che, Y., Datar, A., Yang, X., Naddo, T., Zhao, J., and Zang, L. J. Am. Chem. Soc. 2007, 129, 6354-6355