Systematic investigation of PPV analogue oligomers incorporating low-coordinate phosphorus centres

European Journal of Inorganic Chemistry

Volumn , Issue 5, 2004, Pages 998-1006

  Smith, Rhett C ^a   Protasiewicz, John D ^a  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

Author keywords

Oligomers; Phosphaalkenes; Phosphorus

Indexed keywords

LIGANDS; OLIGOMERS;

BULKY LIGANDS; CONJUGATED SYSTEMS; DIPHOSPHENES; ELECTRONIC COMMUNICATIONS; EXPERIMENTAL EVIDENCE; EXTENDED SYSTEMS; PHOSPHAALKENES; PPV OLIGOMERS; RED SHIFT;

PHOSPHORUS;

ALKANE DERIVATIVE; ALKENE DERIVATIVE; CARBON; OLIGOMER; POLY(4 PHENYLENEVINYLENE); UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CONJUGATION; ELECTRONICS; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 4544376719     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejic.200300551     Document Type: Article

References (72)

1. [1a] H. Shirakawa, E. J. Louis, A. G. MacDiarmid, C. K. Chiang, A. J. Heeger, J. Chem. Soc., Chem. Commun. 1977, 578.
2. [1b] C. K. Chiang, C. R. Fincher, Y. W. Park, A. J. Heeger, H. Shirakawa, E. J. Louis, Phys. Rev. Lett. 1977, 39, 1098.
3. J. H. Burroughes, D. D. C. Bradley, A. R. Brown, R. N. Marks, K. MacKay, R. H. Friend, P. L. Burn, A. B. Holmes, Nature 1990, 347, 539-541.
4. [3a] H. Shirakawa, Angew. Chem. Int. Ed. 2001, 40, 2574-2580.
5. [3b] A. G. MacDiarmid, Angew. Chem. Int. Ed. 2001, 40, 2581-2590.
6. [3c] A. J. Heeger, Angew. Chem. Int. Ed. 2001, 40, 2591-2611.
7. [3d] Handbook of Conductive Materials and Polymers (Ed.: H. S. Nalwa); John Wiley & Sons: New York, 1997.
8. [3f] Handbook of Conducting Polymers, 2 ed. (Eds.: T. A. Skotheim, R. L. Elsenbaumer, J. R. Reynolds); Dekker: New York, 1998.
9. A. Kraft, A. C. Grimsdale, A. B. Holmes, Angew. Chem. Int. Ed. 1998, 37, 402-428, and references cited therein.
10. Phosphorus: The Carbon Copy (Eds.: K. B. Dillon, F. Mathey, J. F. Nixon); John Wiley & Sons: New York, 1998.
11. [6a] Multiple Bonds and Low Coordination in Phosphorus Chemistry (Eds.: M. Regitz, O. J. Scherer); Thieme Verlag: Stuttgart, 1990.
12. [6b] L. Nyulaszi, T. Veszpremi, J. Reffy, J. Phys. Chem. 1993, 97, 4011-4015.
13. [6c] P. P. Power, Chem. Rev. 1999, 99, 3463-3503.
14. V. A. Wright, D. P. Gates, Angew. Chem. Int. Ed. 2002, 41, 2389-2392.
15. R. C. Smith, X. Chen, J. D. Protasiewicz, Inorg. Chem. 2003, 42, 5468-5470.
16. C. Fave, T.-Y. Cho, M. Hissler, C.-W. Chen, T.-Y. Luh, C.-C. Wu, R. Reau, J. Am. Chem. Soc. 2003, 125; 9254-9255.
17. F. Mathey, Angew. Chem. Int. Ed. 2003, 42, 1578-1604.
18. J. Zhou, B. L. Lucht, J. Organomet. Chem. 2002, 653, 167-176.
19. [12a] S. S. H. Mao, T. D. Tilley, Macromolecules 1997, 30, 5566-5569.
20. [12b] This group has also incorporated germoles into conjugated polymers: B. L. Lucht, M. A. Buretea, T. D. Tilley, Organometallics 2000, 19, 3469-3475.
21. H. P. Withers, D. Seyferth, Organometallics 1982, 1, 1283-1288.
22. C. H. Honeyman, D. A. Foucher, F. Y. Dahmen, R. Rulkens, A. J. Lough, I. Manners, Organometallics 1995, 14, 5503-5512.
23. N. H. T. Huy, L. Ricard, F. Mathey, Angew. Chem. Int. Ed. 2001, 40, 1253-1255.
24. E. Deschamps, L. Ricard, F. Mathey, Angew. Chem. Int. Ed. Engl. 1994, 33, 1158-1161.
25. [17a] M.-O. Bevierre, F. Mercier, L. Ricard, F. Mathey, Angew. Chem. Int. Ed. Engl. 1990, 29, 655-657.
26. [17b] M.-O. Bevierre, F. Mercier, L. Ricard, F. Mathey, A. Jutland, C. Amatore, New J. Chem. 1991, 15, 545-550.
27. [18a] C. Hay, C. Fischmeister, M. Hissler, L. Toupet, R. Reau, Angew. Chem. Int. Ed. 2000, 39, 1812-1815.
28. [18b] C. Hay, M. Hissler, C. Fischmeister, J. Rault-Berthelot, L. Toupet, L. Nyulaszi, R. Reau, Chem. Eur. J. 2001, 7, 4222-4236.
29. [18c] C. Hay, M. Sauthier, M. Hissler, L. Nyulaszi, R. Reau, Phosphorus, Sulfur, and Relat Elem. 2002, 177, 1423-1425.
30. [19a] K. Müllen, G. Wegner, (Eds.) Electronic Materials. The Oligomer Approach; Wiley-VCH: New York, 1998.
31. [19b] J. M. Tour, Chem. Rev. 1996, 96, 537-553.
32. [19c] P. F. van Hutten, V. V. Krasnikov, G. Hadziioannou, Acc. Chem. Res. 1999, 32, 257-265.
33. [20a] A. A. Badri, A. Jouaiti, M. Geoffroy, Mag. Res. Chem. 1999, 37, 735-742.
34. [20b] M. Geoffroy, M. J. Cattani-Lorente, Chem. Phys. Phys.-Chim. Biol. 1991, 88, 1159-1166.
35. [20c] A. Jouaiti, A. A. Badri, M. Geoffroy, G. Bernardinelli, J. Organomet. Chem. 1997, 529, 143-149.
36. C. Dutan, S. Shah, R. C. Smith, S. Choua, T. Berclaz, M. Geoffroy, J. D. Protasiewicz, Inorg. Chem. 2003, 42, 6241-6251.
37. S. Shah, T. Concolino, A. L. Rheingold, J. D. Protasiewicz, Inorg. Chem. 2000, 39, 3860-3867.
38. H. Kawanami, K. Toyota, M. Yoshifuji, J. Organomet. Chem. 1997, 535, 1-5.
39. L. Weber, Chem. Rev. 1992, 92, 1839-1906.
40. M. Yoshifuji, I. Shima, N. Inamoto, K. Hirotsu, T. Higuchi, J. Am. Chem. Soc. 1981, 103, 4587-4589.
41. [26a] N. Burford, J. A. C. Clyburne, M. S. W. Chan, Inorg. Chem. 1998, 3204-3206.
42. [26b] K. W. Klinkhammer, Angew. Chem. Int. Ed. Engl. 1997, 2320-2322.
43. [27a] P. P. Power, Adv. Organomet. Chem. 1999, 32, 1-65.
44. [27b] G. H. Robinson, Acc. Chem. Res. 1999, 32, 773.
45. [27c] J. A. C. Clyburne, N. McMullen, Coord. Chem. Rev. 2000, 210, 73-99.
46. [28a] K. Tsuji, S. Sasaki, M. Yoshifuji, Tetrahedron Lett. 1999, 40, 3203-3206.
47. [28b] S. Sasaki, H. Aoki, K. Sutoh, S. Hakiri, K. Tsuji, M. Yoshifuji, Helv. Chim. Acta 2002, 85, 3842-3847.
48. A. Saednya, H. Hart, Synthesis 1996, 1455-1458.
49. R. M. Letch, Org. Magn. Reson. 1981, 16, 220-223.
50. [31a] J. S. Cha, H. C. Brown, J. Am. Chem. 1993, 58, 4727-4731.
51. [31b] I. F. Cottrell, D. H. Hands, G. Peter, G. R. Humphrey, S. H. B. Wright, J. Heterocycl. Chem. 1991, 28, 301-304.
52. [31c] H. Irngartinger, B. Stadler, Eur. J. Org. Chem. 1998, 4, 605-626.
53. S. Younes, G. Tchani, G. Baziard-Mouysset, J. L. Stigliani, M. Payard, Eur. J. Med. Chem. Chim. Ther. 1994, 29, 87-94.
54. [33a] T. Sawada, M. Wakabayashi, H. Takeo, A. Miyazawa, M. Tashiro, J. Chem. Soc., Perkin Trans. 1 1999, 403-408.
55. [33b] C. Bellucci, G. Gualtieri, A. Chiarini, Eur. J. Med. Chem. Chim. Ther. 1987, 22, 473-478.
56. K. Ruhlandt-Senge, J. J. Ellison, R. J. Wehmschulte, F. Pauer, P. P. Power, J. Am. Chem. Soc. 1993, 115, 11353-11357.
57. [35a] T. L. Alan, A. C. Scheiner, Y. Yamaguchi, H. F. Schaefer III, J. Am. Chem. Soc. 1986, 108, 7579-7588.
58. [35b] S. Elbel, A. Ellis, E. Nieke, H. Egsgaard, L. Carlsen, J. Chem. Soc., Dalton Trans. 1985, 879-884.
59. [35c] A. H. Cowley, Polyhedron 1984, 3, 389-432.
60. [35d] S. Nagase, S. Suzuki, T. Kurakake, Chem. Commun. 1990, 1724-1726.
61. A. H. Cowley, A. Decken, N. C. Norman, C. Kruger, F. Lutz, H. Jacobsen, T. Ziegler, J. Am. Chem. Soc. 1997, 119, 3389-3390.
62. D. Cao, D. Schollmeyer, H. Meier, Eur. J. Org. Chem. 1999, 791-796.
63. S.-J. Chung, D. W. Lee, O. Dong-Keun, J.-I. Jin, Acta Polym. 1999, 50, 298-303.
64. D. T. McQuaid, A. E. Pullen, T. M. Swager, Chem. Rev. 2000, 100, 2537-2574, and references cited therein.
65. [40a] H. Kawanami, K. Toyota, M. Yoshifuji, J. Organomet. Chem. 1997, 535, 1-5.
66. [40b] H. Kawanami, K. Toyota, M. Yoshifuji, Chem. Lett. 1996, 7, 533-534.
67. R. C. Smith, S. Shah, E. Urnezius, J. D. Protasiewicz, J. Am. Chem. Soc. 2003, 125, 40-41.
68. W. W. Simmons, The Stadtler Handbook of Ultraviolet Spectra, Stadtler Research Laboratories, Philadelphia, 1979.
69. R. F. Heck, J. Organomet. Chem. 1972, 37, 389-396.
70. [44a] S. Shah, J. D. Protasiewicz, Chem. Commun. 1998, 1585-1586.
71. [44b] S. Shah, J. D. Protasiewicz, Coord. Chem. Rev. 2000,210, 181-201.
72. E. Urnezius, J. D. Protasiewicz, Main Group Chemistry 1996, 1, 369-372.