Synthesis and structural characterization of a TCNQ based organic semi-conducting material with a 2:5 stoichiometry

Journal of Organic Chemistry

Volumn 76, Issue 24, 2011, Pages 10078-10082

  Lu, Jinzhen ^a   Qu, Xiaohu ^a   Peleckis, Germanas ^b   Boas, John F ^a   Bond, Alan M ^a   Martin, Lisandra L ^a  

^a MONASH UNIVERSITY   (Australia)

^b UNIVERSITY OF WOLLONGONG   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRICAL CONDUCTIVITY MEASUREMENTS; ORGANIC SEMICONDUCTOR; QUASI-ONE-DIMENSIONAL; RAMAN SPECTRUM; STRUCTURAL CHARACTERIZATION; TETRABUTYLAMMONIUM;

ELECTRIC CONDUCTIVITY; MAGNETIC SUSCEPTIBILITY; X RAY CRYSTALLOGRAPHY;

STOICHIOMETRY;

7,7',8,8' TETRACYANOQUINODIMETHANE; CATION; METHANE; METHANOL; ORGANIC COMPOUND; SOLVENT; TETRABUTYLAMMONIUM; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; DIFFUSION; ELECTRIC CONDUCTIVITY; ELECTROCHEMISTRY; ELECTRON SPIN RESONANCE; EVAPORATION; FILTRATION; INFRARED SPECTROSCOPY; MAGNETISM; MEASUREMENT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RAMAN SPECTROMETRY; ROOM TEMPERATURE; SEMICONDUCTOR; SOLID STATE; STOICHIOMETRY; STRUCTURE ANALYSIS; SURFACE CHARGE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 84055200138     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2018334     Document Type: Article

References (47)

1. Acker, D. S.; Harder, R. J.; Hertler, W. R.; Mahler, W.; Melby, L. R.; Benson, R. E.; Mochel, W. E. J. Am. Chem. Soc. 1960, 82, 6408-6409.
2. Melby, L. R.; Mahler, W.; Mochel, W. E.; Harder, R. J.; Hertler, W. R.; Benson, R. E. J. Am. Chem. Soc. 1962, 84, 3374-3387.
3. Torrance, J. B. Mol. Cryst. Liq. Cryst. 1985, 126, 55-67.
4. Qu, X.; Lu, J.; Zhao, C.; Boas, J. F.; Moubaraki, B.; Murray, K. S.; Siriwardana, A.; Bond, A. M.; Martin, L. L. Angew. Chem., Int. Ed. 2011, 50, 1589-1592.
5. Bond, A. M. Broadening Electrochemical Horizons: Principles and Illustration of Voltammetric and Related Techniques; Oxford University Press: Oxford, 2002; Chapter 5.
6. Kirtley, J. R.; Mannhart, J. Nat. Mater. 2008, 7, 520-521.
7. Kivala, M.; Boudon, C.; Gisselbrecht, J. P.; Seiler, P.; Gross, M.; Diederich, F. Chem. Commun. 2007, 4731-4733.
8. Jain, R.; Kabir, K.; Gilroy, J. B.; Mitchell, K. A. R.; Wong, K. C.; Hicks, R. G. Nature 2007, 445, 291-294.
9. Nafady, A.; Bond, A. M. Inorg. Chem. 2007, 46, 4128-4137.
10. O'Mullane, A. P.; Neufeld, A. K.; Harris, A. R.; Bond, A. M. Langmuir 2006, 22, 10499-10505.
11. Neufeld, A. K.; O'Mullane, A. P.; Bond, A. M. J. Am. Chem. Soc. 2005, 127, 13846-13853.
12. Hu, Z. P.; Shen, Z. X.; Qin, L.; Tang, S. H.; Kuok, M. H.; Xu, G. Q.; Mok, K. F.; Huang, H. H. J. Mol. Struct. 1995, 356, 163-168.
13. Wallace, W. L.; Jaeger, C. D.; Bard, A. J. J. Am. Chem. Soc. 1979, 101, 4840-4843.
14. Mochida, T.; Yamazaki, S.; Suzuki, S.; Shimizu, S.; Mori, H. Bull. Chem. Soc. Jpn. 2003, 76, 2321-2328.
15. Bond, A. M.; Colton, R.; van den Bergen, A.; Walter, J. N. Organometallics 2004, 23, 3164-3176.
16. Herbstein, F. H.; Kapon, M. Crystallogr. Rev. 2008, 14, 3-74.
17. Kuroda, N.; Sugimoto, T.; Hagiwara, M.; Hasanudin.; Ueda, K.; Tada, T.; Uozaki, H.; Toyota, N.; Mogi, I.; Watanabe, K.; Motokawa, M. Synth. Met. 2003, 133, 535-537.
18. Andrzej, G.; Andrzej, B. Mini-Rev. Med. Chem. 2010, 7, 145-160.
19. Chen, Y. C.; Liu, G. X.; Wang, P. F.; Xu, H.; Ren, X. M.; Song, Y.; Sui, Y. X. Polyhedron 2007, 26, 1781-1786.
20. Chen, Y. C.; Wang, P. F.; Liu, G. X.; Xu, H.; Ren, X. M.; Song, Y.; Ni, Z. P. J. Phys. Chem. Solids 2008, 69, 2445-2452.
21. Martin, L. L.; Siriwardana, A.; Lu, J.; Qu, X.; Zhao, C.; Bond, A. M. Aust. J. Chem. 2011, 64, 732-740.
22. Qu, X.; Lu, J.; Boas, J. F.; Bond, A. M.; Martin, L. L. Eur. J. chem. 2011, 17, 9350-9358.
23. Torrance, J. B. Acc. Chem. Res. 1979, 12, 79-86.
24. Garito, A. F.; Heeger, A. J. Acc. Chem. Res. 1975, 7, 232-240.
25. Ashwell, G. J.; Eley, D. D.; Wallwork, S. C.; Willis, M. R.; Welch, G. D.; Woodward, J. Acta Crystallogr. 1977, B33, 2252-2257.
26. Ashwell, G. J.; Wallwork, S. C.; Baker, S. R.; Berthier, P. I. Acta Crystallogr. 1975, B31, 1174-1178.
27. Ashwell, G. J.; Bartlett, V. E.; Eley, D. D.; Wallwork, S. C.; Willis, M. R. Acta Crystallogr. 1977, B33, 2602-2607.
28. Ashwell, G. J.; Eley, D. D.; Drew, N. J.; Wallwork, S. C.; Willis, M. R. Acta Crystallogr. 1977, B33, 2598-2602.
29. Ashwell, G. J.; Eley, D. D.; Fleming, R. J.; Wallwork, S. C.; Willis, M. R. Acta Crystallogr. 1976, B32, 2948-2952.
30. Ashwell, G. J.; Eley, D. D.; Harper, A.; Torrance, A. C.; Wallwork, S. C.; Willis, M. R. Acta Crystallogr. 1977, B33, 2258-2263.
31. Ashwell, G. J.; Eley, D. D.; Drew, N. J.; Wallwork, S. C.; Willis, M. R. Acta Crystallogr. 1978, B34, 3608-3612.
32. Ashwell, G. J.; Eley, D. D.; Willis, M. R. Nature 1976, 259, 201-202.
33. Ueda, K.; Sugimoto, T.; Endo, S.; Toyota, N.; Kohama, M.; Yamamoto, K.; Suenaga, Y.; Morimoto, H.; Yamaguchi, T.; Munakata, M.; Hosoito, N.; Kanehisa, N.; Shibamoto, Y.; Kai, Y. Chem. Phys. Lett. 1996, 261, 295-300.
34. O'Kane, S. A.; Clerac, R.; Zhao, H. H.; Xiang, O. Y.; Galan-Mascaros, J. R.; Heintz, R.; Dunbar, K. R. J. Solid State Chem. 2000, 152, 159-173.
35. Herbstein, F. H. Crystalline Molecular Complexes and Compounds; Oxford University Press: Oxford, 2005; Vols. 1 and 2.
36. Flandrois, P. S.; Chasseau, D. Acta Crystallogr., Sect. B 1977, 33, 2744-2750.
37. Kistenmacher, T. J.; Emge, T. J.; Bloch, A. N.; Cowan, D. O. Acta Crystallogr., Sect. B 1982, 38, 1193-1199.
38. Epstein, A. J.; Conwell, E. M.; Miller, J. S. Ann. N.Y. Acad. Sci. 1978, 313, 183-209.
39. Schwoerer, M.; Wolf, H. C. Organic Molecular Solids; Wiley VCH: Weiheim, 2007.
40. Ashwell, G. L.; Jansen, S.; Jones, M. T.; Kennard, C. H. L. Phys. Stat. Sol. A 1983, 80, 127-134.
41. Bonner, J. C.; Fisher, M. E. Phys. Rev. 1964, 135A, 640-658.
42. Graja, A. Low Dimensional Organic Conductors; World Scientific: Singapore, 1992.
43. Peng, H.; Ran, C.; Liu, Z.; Long, Y.; Wang, Z.; Yu, Z.; Sun, H.; Wei, Y.; Gao, S.; Chen, Z.; Chen, E.-Q. J. Phys. Chem. C 2008, 112, 11001-11006.
44. Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112-122.
45. Barbour, L. J. J. Supramol. Chem 2001, 1, 189.
46. Wertz, J. E.; Orton, J. W.; Auzins, P. Disc. Faraday Soc. 1961, 31, 140-150.
47. Hanson, G. R.; Gates, K. E.; Noble, C. J.; Griffin, M.; Mitchell, A.; Benson, S. J. Inorg. Biochem. 2004, 98, 903-916.