Rapid solid-phase syntheses of conjugated homooligomers and [AB] alternating block cooligomers of precise length and constitution

Journal of Organic Chemistry

Volumn 64, Issue 24, 1999, Pages 8898-8906

  Huang, Shenlin ^a   Tour, James M ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

OLIGOMER;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; DECOMPOSITION; OLIGOMERIZATION; SYNTHESIS;

EID: 0033607470     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991201s     Document Type: Article

References (37)

1. Tour, J. M. Chem. Rev. 1996, 96, 537.
2. (a) Zhou, C.; Deshpande, M. R.; Reed, M. A.; Jones, L., II; Tour, J. M. Appl. Phys. Lett. 1987, 71, 611.
3. (b) Reinerth, W. A.; Jones, L., II.; Burgin, T. P.; Zhou, C.-W.; Muller, C. J.; Deshpande, M. R.; Reed, M. A.; Tour, J. M. Nanotechnology 1998, 9, 246.
4. (c) Tour, J. M.; Kozaki, M.; Seminario, J. M. J. Am. Chem. Soc. 1998, 120, 8486.
5. (d) Cygan, M. T.; Dunbar, T. D.; Arnold, J. J.; Bumm, L. A.; Shedloch, N. P.; Burgin, T. P.; Jones, L., II.; Allara, D. L.; Tour, J. M.; Weiss, P. S. J. Am. Chem. Soc. 1998, 120, 2721.
6. For routes to oligo(phenylene ethynylene)s, see (a) Zhang, J.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1992, 31, 922. (b) Young, J. K.; Nelson, J. C.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 10841. (c) Golt, A.; Ziener, U. J. Org. Chem. 1997, 62, 6137. (d) Jones, L., II.; Schumm, J. S.; Tour, J. M. J. Org. Chem. 1997, 62, 1388. (e) Schumm, J. S.; Pearson, D. L.; Tour, J. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1360. (f) Huang, S.; Tour, J. M. J. Am. Chem. Soc. 1999, 121, 4908. For routes to oligo(thiophene ethynylene)s, see: (g) Pearson, D. L.; Tour, J. M. J. Org. Chem. 1997, 62, 1376. (h) Pearson, D. L.; Schumm, J. S.; Tour, J. M. Macromolecules 1994, 27, 2348.
7. For routes to oligo(phenylene ethynylene)s, see (a) Zhang, J.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1992, 31, 922. (b) Young, J. K.; Nelson, J. C.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 10841. (c) Golt, A.; Ziener, U. J. Org. Chem. 1997, 62, 6137. (d) Jones, L., II.; Schumm, J. S.; Tour, J. M. J. Org. Chem. 1997, 62, 1388. (e) Schumm, J. S.; Pearson, D. L.; Tour, J. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1360. (f) Huang, S.; Tour, J. M. J. Am. Chem. Soc. 1999, 121, 4908. For routes to oligo(thiophene ethynylene)s, see: (g) Pearson, D. L.; Tour, J. M. J. Org. Chem. 1997, 62, 1376. (h) Pearson, D. L.; Schumm, J. S.; Tour, J. M. Macromolecules 1994, 27, 2348.
8. For routes to oligo(phenylene ethynylene)s, see (a) Zhang, J.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1992, 31, 922. (b) Young, J. K.; Nelson, J. C.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 10841. (c) Golt, A.; Ziener, U. J. Org. Chem. 1997, 62, 6137. (d) Jones, L., II.; Schumm, J. S.; Tour, J. M. J. Org. Chem. 1997, 62, 1388. (e) Schumm, J. S.; Pearson, D. L.; Tour, J. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1360. (f) Huang, S.; Tour, J. M. J. Am. Chem. Soc. 1999, 121, 4908. For routes to oligo(thiophene ethynylene)s, see: (g) Pearson, D. L.; Tour, J. M. J. Org. Chem. 1997, 62, 1376. (h) Pearson, D. L.; Schumm, J. S.; Tour, J. M. Macromolecules 1994, 27, 2348.
9. For routes to oligo(phenylene ethynylene)s, see (a) Zhang, J.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1992, 31, 922. (b) Young, J. K.; Nelson, J. C.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 10841. (c) Golt, A.; Ziener, U. J. Org. Chem. 1997, 62, 6137. (d) Jones, L., II.; Schumm, J. S.; Tour, J. M. J. Org. Chem. 1997, 62, 1388. (e) Schumm, J. S.; Pearson, D. L.; Tour, J. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1360. (f) Huang, S.; Tour, J. M. J. Am. Chem. Soc. 1999, 121, 4908. For routes to oligo(thiophene ethynylene)s, see: (g) Pearson, D. L.; Tour, J. M. J. Org. Chem. 1997, 62, 1376. (h) Pearson, D. L.; Schumm, J. S.; Tour, J. M. Macromolecules 1994, 27, 2348.
10. For routes to oligo(phenylene ethynylene)s, see (a) Zhang, J.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1992, 31, 922. (b) Young, J. K.; Nelson, J. C.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 10841. (c) Golt, A.; Ziener, U. J. Org. Chem. 1997, 62, 6137. (d) Jones, L., II.; Schumm, J. S.; Tour, J. M. J. Org. Chem. 1997, 62, 1388. (e) Schumm, J. S.; Pearson, D. L.; Tour, J. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1360. (f) Huang, S.; Tour, J. M. J. Am. Chem. Soc. 1999, 121, 4908. For routes to oligo(thiophene ethynylene)s, see: (g) Pearson, D. L.; Tour, J. M. J. Org. Chem. 1997, 62, 1376. (h) Pearson, D. L.; Schumm, J. S.; Tour, J. M. Macromolecules 1994, 27, 2348.
11. For routes to oligo(phenylene ethynylene)s, see (a) Zhang, J.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1992, 31, 922. (b) Young, J. K.; Nelson, J. C.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 10841. (c) Golt, A.; Ziener, U. J. Org. Chem. 1997, 62, 6137. (d) Jones, L., II.; Schumm, J. S.; Tour, J. M. J. Org. Chem. 1997, 62, 1388. (e) Schumm, J. S.; Pearson, D. L.; Tour, J. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1360. (f) Huang, S.; Tour, J. M. J. Am. Chem. Soc. 1999, 121, 4908. For routes to oligo(thiophene ethynylene)s, see: (g) Pearson, D. L.; Tour, J. M. J. Org. Chem. 1997, 62, 1376. (h) Pearson, D. L.; Schumm, J. S.; Tour, J. M. Macromolecules 1994, 27, 2348.
12. For routes to oligo(phenylene ethynylene)s, see (a) Zhang, J.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1992, 31, 922. (b) Young, J. K.; Nelson, J. C.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 10841. (c) Golt, A.; Ziener, U. J. Org. Chem. 1997, 62, 6137. (d) Jones, L., II.; Schumm, J. S.; Tour, J. M. J. Org. Chem. 1997, 62, 1388. (e) Schumm, J. S.; Pearson, D. L.; Tour, J. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1360. (f) Huang, S.; Tour, J. M. J. Am. Chem. Soc. 1999, 121, 4908. For routes to oligo(thiophene ethynylene)s, see: (g) Pearson, D. L.; Tour, J. M. J. Org. Chem. 1997, 62, 1376. (h) Pearson, D. L.; Schumm, J. S.; Tour, J. M. Macromolecules 1994, 27, 2348.
13. For routes to oligo(phenylene ethynylene)s, see (a) Zhang, J.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1992, 31, 922. (b) Young, J. K.; Nelson, J. C.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 10841. (c) Golt, A.; Ziener, U. J. Org. Chem. 1997, 62, 6137. (d) Jones, L., II.; Schumm, J. S.; Tour, J. M. J. Org. Chem. 1997, 62, 1388. (e) Schumm, J. S.; Pearson, D. L.; Tour, J. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1360. (f) Huang, S.; Tour, J. M. J. Am. Chem. Soc. 1999, 121, 4908. For routes to oligo(thiophene ethynylene)s, see: (g) Pearson, D. L.; Tour, J. M. J. Org. Chem. 1997, 62, 1376. (h) Pearson, D. L.; Schumm, J. S.; Tour, J. M. Macromolecules 1994, 27, 2348.
14. (a) Polymer-Supported Reactions in Organic Synthesis; Hodge, P., Sherrington, D. C., Eds.; Wiley: New York, 1980.
15. (b) Fruchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17.
16. (c) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527.
17. (d) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
18. (e) Malenfant, P. R. L.; Fréchet, J. M. J. Chem. Commun. 1998, 2657.
19. (f) Hodge, P. Chem. Soc. Rev. 1997, 26, 417.
20. Kraus, G. A.; Landgrebe, K. Synthesis 1984, 885.
21. Kumada, M.; Tamao, K.; Sumitani, K. Org. Synth. 1978, 58, 127
22. Suzuki, H.; Nakamura, K.; Goto, R. Bull. Chem. Soc. Jpn. 1966, 39, 128.
23. Weingarten, M. D.; Padwa, A. Tetrahedron Lett. 1995, 36, 4717.
24. (a) Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627.
25. (b) MacBride, J. A. H.; Wade, K. Synth. Commun. 1996, 26, 2309.
26. Thompson, L. A.; Ellman, J. A. Tetrahedron Lett. 1994, 35, 9333.
27. (a) Suffert, J.; Ziessel, R. Tetrahedron Lett. 1991, 32, 757.
28. (b) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467.
29. (c) Stephens, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 3313.
30. (d) For application of this reaction to poly[(1,4-phenylene ethynylene)-alt-(2,5-thiophene ethynylene)]s, see: Li, J.; Pang, Y. Macromolecules 1998, 31, 5740.
31. Quirk, R. P.; Kinning, D. J.; Fetters, L. J. In Comprehensive Polymer Science; Aggarwal, S. L., Ed., Pergamon Press Inc: New York, 1989; Vol. 7, p 1.
32. Li, W.; Maddux, T.; Yu, L. Macromolecules 1990, 29, 7329.
33. Müllen, K.; Wegner, G. Adv. Mater. 1998, 10, 433.
34. (a)Yan, B.; Kumaravel, G.; Anjaria, H.; Wu, A.; Petter, R. C.; Jewell, C. F., Jr.; Wareing, J. R. J. Org. Chem. 1995, 60, 5736.
35. (b) Grindley, T. B.; Johnson, D. F.; Katritzky, A. R.; Keogh, H. J.; Thirkettle, C.; Topsom, R. D. J. Chem. Soc., Perkin Trans. 2 1974, 3, 282.
36. (a) Heitz, W. Polym. Prepr. (Am. Chem. Soc. Div. Polym. Chem.) 1991, 32(1), 327.
37. (b) Solomin, V. A.; Heitz, W. Macromol. Chem. Phys. 1994, 195, 303.