Bis(phosphine imide)s: Easily tunable organic electron donors

Journal of Organic Chemistry

Volumn 70, Issue 19, 2005, Pages 7737-7743

  Guidi, Vanina V ^a   Jin, Zhou ^a   Busse, Devin ^a   Euler, William B ^a   Lucht, Brett L ^a  

^a University of Rhode Island   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; ELECTROCHEMISTRY; FREE RADICALS; OXIDATION; PHOSPHORUS COMPOUNDS; PROBABILITY DENSITY FUNCTION; SPECTROSCOPIC ANALYSIS; SUBSTITUTION REACTIONS;

AROMATIC LINKER; BIS(PHOSPHINE IMIDE); QUINONODIAL DICATIONIC STATE; SINGLE-ELECTRON OXIDATION;

ELECTRONS;

4 PHENYLENEBIS(PHOSPHINE IMIDE) DERIVATIVE; 4,4' BIPHENYLENE [BIS(TRIPHENYL)PHOSPHINE IMIDE]; BIS(PHOSPHINE IMIDE) DERIVATIVE; CATION; IMIDE; PHOSPHINE DERIVATIVE; PHOSPHORUS; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CARBON NUCLEAR MAGNETIC RESONANCE; DENSITY FUNCTIONAL THEORY; ELECTROCHEMISTRY; ELECTRON TRANSPORT; INFRARED SPECTROSCOPY; NEAR INFRARED SPECTROSCOPY; OXIDATION REDUCTION POTENTIAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; ULTRAVIOLET SPECTROSCOPY; VIBRATION;

EID: 24944465004     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051196u     Document Type: Article

References (42)

1. (a) Handbook of Conducting Polymers; Skotheim, T. A., Ed.; Marcel Dekker: New York, 1986.
2. (b) Fichou, D. In Conjugated Polymers: The Novel Science and Technology of Highly Conducting and Nonlinear Optically Active Materials; Bredas, J. L., Silbey, R., Eds.; Kluwer Academic: Dordecht, The Netherlands, 1991.
3. Burroughs, J. H.; Bradley, D. D. C.; Brown, A. R.; Marks, R. N.; Mackay, K.; Friend, R. H.; Burns, P. L.; Holmes, A. B. Nature 1990, 347, 539.
4. Kraft, A.; Grimsdale, A. C.; Holmes, A. B. Angew. Chem., Int. Ed. 1998, 37, 402.
5. Anderson, J. D.; McDonald, E. M.; Lee, P. A.; Anderson, M. L.; Ritchie, E. L.; Hall, H. K.; Hopkins, T.; Mash, E. A.; Wang, J.; Padias, A.; Thayumanavan, S.; Barlow, S.; Marder, S. R.; Jabbour, G. E.; Shaheen, S.; Kippelen, B.; Peyghambarian, N.; Wightman, R. M.; Armstrong, N. R. J. Am. Chem. Soc. 1998, 120, 9646.
6. Ferraro, J. R.; Williams, J. M. Introduction to Synthetic Electrical Conductors; Academic Press: Orlando, FL, 1987.
7. Cosmina, D.; Shashin, S.; Smith, R. C.; Choua, S.; Berclaz, T.; Geoffroy, M.; Protasiewicz, J. D. Inorg. Chem. 2003, 42, 6241.
8. (a) Bevierre, M. O.; Mercier, F.; Ricard, L.; Mathey, F. Angew. Chem., Int. Ed. Engl. 1990, 29, 655.
9. (b) Deschamps, E.; Ricard, L.; Mathey, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 1158.
10. (a) Lucht, B. L.; St. Onge, N. O. Chem. Commun. 2000, 2097.
11. (b) Jin, Z.; Lucht, B. L. J. Organomet. Chem. 2002, 653, 167.
12. (c) Jin, Z.; Lucht, B. L. J. Am. Chem. Soc. 2005, 127, 5586.
13. (a) Wright, V. A.; Gates, D. P. Angew. Chem., Int. Ed. 2002, 41, 2389.
14. (b) Smith, R. C.; Chen, X.; Protasiewicz, J. D. Inorg. Chem. 2003, 42, 5468.
15. (a) Blonsky, P. M.; Shriver, D. F.; Austin, P.; Allcock, H. R. J. Am. Chem. Soc. 1984, 106, 6854.
16. (b) Gray, F. M. Solid Polymer Electrolytes: Fundamentals and Technological Applications; VCH: New York, 1991.
17. (c) Neilson, R. H. Phosphorus-Nitrogen Compounds. In Encyclopedia of Inorganic Chemistry; King, B. R., Ed.; Wiley & Sons: New York, 1994; Vol. 6, pp 3180-3199.
18. Sudhakar, P. V.; Lammertsma, K. J. Am. Chem. Soc. 1991, 113, 1899.
19. Wiegrabe, W.; Bock, H. Chem. Ber. 1968, 101, 1414.
20. Escobar, M.; Jin, Z.; Lucht, B. L. Org. Lett. 2002, 2213.
21. Abel, E. W.; Mucklejohn, S. A. Phosphorus Sulfur 1981, 9, 235.
22. Herring, D. L. J. Org. Chem. 1961, 26, 3998.
23. Khmurova, I. N.; Yurchenko, V. G.; Kukhar, V. P.; Zolotareva, L. A. Zh. Obshch. Khim. 1974, 44, 74.
24. Homer, L.; Oediger, H. Ann. 1959, 627, 142.
25. Torrance, J. B. Mol. Cryst. Liq. Cryst. 1985, 126, 55.
26. Roncali, J. J. Mater. Chem. 1997, 12, 2307.
27. Laboratory Techniques in Electroanalytical Chemistry; Kissinger, P. T., Heineman, W. R., Eds.; Marcel Dekker: New York, 1985.
28. Barriere, F.; Camire, N.; Geiger, W. E.; Mueller-Westerhoff, U. T.; Sanders, R. J. Am. Chem. Soc. 2002, 124, 7262.
29. Lambert, C.; Noll, G. J. Am. Chem. Soc. 1999, 121, 8434.
30. Nelsen, S. F.; Kessel, C. R.; Brien, D. J. J. Am. Chem. Soc. 1980, 102, 702.
31. Shida, T. Electronic Absorption Spectra of Radical Ions; Elsevier: Amsterdam, 1988.
32. Bailey, S. E.; Zink, J. I.; Nelsen, S. F. J. Am. Chem. Soc. 2003, 125, 5939.
33. Nelsen, S. F.; Weaver, M. N.; Telo, J. P.; Lucht, B. L.; Barlow, S. J. Org. Chem. Submitted.
34. Nelsen, S. F. Chem.-Eur. J. 2000, 6, 581.
35. Brunschwig, B. S.; Creutz, C.; Sutin, N. Chem. Soc. Rev. 2002, 31, 168.
36. Hewlins, M. J. E. J. Chem. Soc. B 1971, 942.
37. Dunne, B. J.; Morris, R. B.; Orpen, A. G. J. Chem. Soc., Dalton Trans. 1991, 653.
38. Spartan for Linux; Wavefunction, Inc.: Irvine, CA.
39. Robin, M.; Day, P. Adv. Inorg. Chem. Radiochem. 1967, 10, 247.
40. Nelsen, S. F.; Tran, H. Q.; Nagy, M. A. J. Am. Chem. Soc. 1998, 120, 298.
41. Gilheany, D. G. Chem. Rev. 1994, 94, 1339.
42. Wheland, R. C.; Gillson, J. L. J. Am. Chem. Soc. 1976, 98, 3916.