Rapid Solution and Solid Phase Syntheses of Oligo(1,4-phenylene ethynylene)s with Thioester Termini: Molecular Scale Wires with Alligator Clips. Derivation of Iterative Reaction Efficiencies on a Polymer Support

Journal of Organic Chemistry

Volumn 62, Issue 5, 1997, Pages 1388-1410

  Jones II, LeRoy ^a   Schumm, Jeffry S ^a   Tour, James M ^a  

^a UNIVERSITY OF SOUTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001135635     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962336q     Document Type: Article

References (39)

1. See the preceding article (Pearson, D.; Tour, J. M. J. Org. Chem. 1997, 62, xxx) and references therein for a description of molecular scale electronics, the synthetic organic challenges involved, the efficacy of the iterative divergent/convergent approach for the conjugated structures via the coupling approaches chosen here, and the utility of thiol end groups to act as alligator clips.
2. Schumm, J. S.; Pearson, D. L.; Tour, J. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1360.
3. An iterative divergent/convergent approach has been used to prepare the analogous oligo(1,3-phenylene ethynylenes): (a) Zhang, J.; Moore, J. S.; Xu, Z. F.; Aguirre, R. A. J. Am. Chem. Soc. 1992, 114, 2273. (b) Xu, Z. F.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1993, 32, 1354. For related oligomers and polymers, see: (c) Grubbs, R. H.; Kratz, D. Chem. Ber. 1993, 126, 149. Scherf, U.; Müllen, K. Synthesis 1992, 23. For a recent review on the subject, see: (e) Tour, J. M. Chem. Rev. 1996, 96, 537.
4. An iterative divergent/convergent approach has been used to prepare the analogous oligo(1,3-phenylene ethynylenes): (a) Zhang, J.; Moore, J. S.; Xu, Z. F.; Aguirre, R. A. J. Am. Chem. Soc. 1992, 114, 2273. (b) Xu, Z. F.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1993, 32, 1354. For related oligomers and polymers, see: (c) Grubbs, R. H.; Kratz, D. Chem. Ber. 1993, 126, 149. Scherf, U.; Müllen, K. Synthesis 1992, 23. For a recent review on the subject, see: (e) Tour, J. M. Chem. Rev. 1996, 96, 537.
5. An iterative divergent/convergent approach has been used to prepare the analogous oligo(1,3-phenylene ethynylenes): (a) Zhang, J.; Moore, J. S.; Xu, Z. F.; Aguirre, R. A. J. Am. Chem. Soc. 1992, 114, 2273. (b) Xu, Z. F.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1993, 32, 1354. For related oligomers and polymers, see: (c) Grubbs, R. H.; Kratz, D. Chem. Ber. 1993, 126, 149. Scherf, U.; Müllen, K. Synthesis 1992, 23. For a recent review on the subject, see: (e) Tour, J. M. Chem. Rev. 1996, 96, 537.
6. An iterative divergent/convergent approach has been used to prepare the analogous oligo(1,3-phenylene ethynylenes): (a) Zhang, J.; Moore, J. S.; Xu, Z. F.; Aguirre, R. A. J. Am. Chem. Soc. 1992, 114, 2273. (b) Xu, Z. F.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1993, 32, 1354. For related oligomers and polymers, see: (c) Grubbs, R. H.; Kratz, D. Chem. Ber. 1993, 126, 149. Scherf, U.; Müllen, K. Synthesis 1992, 23. For a recent review on the subject, see: (e) Tour, J. M. Chem. Rev. 1996, 96, 537.
7. An iterative divergent/convergent approach has been used to prepare the analogous oligo(1,3-phenylene ethynylenes): (a) Zhang, J.; Moore, J. S.; Xu, Z. F.; Aguirre, R. A. J. Am. Chem. Soc. 1992, 114, 2273. (b) Xu, Z. F.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1993, 32, 1354. For related oligomers and polymers, see: (c) Grubbs, R. H.; Kratz, D. Chem. Ber. 1993, 126, 149. Scherf, U.; Müllen, K. Synthesis 1992, 23. For a recent review on the subject, see: (e) Tour, J. M. Chem. Rev. 1996, 96, 537.
8. Tour, J. M.; Jones, L., II; Pearson, D. L.; Lamba, J. S.; Burgin, T.; Whitesides, G. W.; Allara, D. L.; Parikh, A. N.; Atre, S. J. Am. Chem. Soc. 1995, 117, 9529.
9. (b) Dhirani, A. A.; Zehner, R. W.; Hsung, R. P.; Guyot-Sionnest, P., Sita, L. R. J. Am. Chem. Soc. 1996, 118, 3319.
10. (c) Bumm, L. A.; Arnold, J. J.; Cygan, M. T.; Dunbar, T. D.; Burgin, T. P.; Jones, L., II, Allara, D. L.; Tour, J. M.; Weiss, P. S. Science 1996, 271, 1705.
11. (a) Young, J. K.; Nelson, J. C.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 10841.
12. (b) Bharathi, P.; Patel U.; Kawaguchi, T.; Pesak, D. J.; Moore, J. S. Macromolecules 1995, 28, 5955.
13. (c) Polymer-Supported Reactions in Organic Synthesis; Hodge, P., Sherrington, D. C., Eds.; Wiley: New York, 1980.
14. (d) Nelson, J. C.; Young, J. K.; Moore, J. S. J. Org. Chem. 1996, 61, 8160.
15. Negishi, E.; King, A. O.; Tour, J. M. Org. Synth. 1985, 64, 44.
16. Doyle, M. P.; Bryker, W. J. J. Org. Chem. 1979, 44, 1572.
17. Lamba, J. S. S.; Tour, J. M. J. Am. Chem. Soc. 1994, 116, 11723.
18. (a) Suffert, J.; Ziessel, R. Tetrahedron Lett. 1991, 32, 757.
19. (b) Sonogashira, K; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467.
20. (c) Stephens, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 3313.
21. Moore, J. S.; Weinstein, E. J.; Wu, Z. Y. Tetrahedron Lett. 1991, 32, 2465.
22. Crowley, J. I.; Rapoport, H. Ace. Chem. Res. 1976, 9, 135.
23. (b) Leznoff, C. C. Chem. Soc. Rev. 1974, 3, 65.
24. (c) Leznoff, C. C. Ace. Chem. Res. 1978, 11, 327.
25. (d) Dewitt, S. H.; Czarnik, A. W.; Ellman, J. A. Ace. Chem. Res. 1996, 29, 114.
26. (e) Giralt, E.; Rizo, J.; Pedroso, E. Tetrahedron 1984, 40, 4141.
27. Van, B; Kumaravel, G; Anjaria, H; Wu, A; Fetter, R. C.; Jewell, C. F., Jr.; Wareing, J. R. J. Org. Chem. 1995, 60, 5736.
28. 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.
29. An analogous equation utilizing resin weight differences has been derived by Moore. See reference 5d.
30. Oligomer lengths were simulated using standard molecular modeling procedures. All calculations were performed on a Power Macintosh 8100/80 AV using Personal CAChe version 3.7 for both structure drawing and minimization. The CAChe mechanics application implements a standard MM2 force field. All energy calculations were minimized over a large number of iterations to convergence at local minima nearest in energy to the starting compounds' energies.
31. (a) Bengton, G.; Keyaniyan, S.; Demeijere, A. Chem. Ber. 1986, 119, 3607.
32. (b) Hurst, D. T.; McInnes, A. G. Can. J. Chem. 1965, 43, 2004.
33. (c) Gaffney, B. L.; Jones, R. A. Tetrahedron Lett. 1982, 23, 2257.
34. Giralt, E.; Rizo, J.; Pedroso, E. Tetrahedron 1984, 40, 4141.
35. McLafferty, F. W.; Turecek, F. Interpretation of Mass Spectra, 4th ed.; University Science: Mill Valley, California, 1993.
36. Briscoe, G. B.; Humphries, S. Talanta 1969, 16, 1403.
37. Zervais, L.; Photaki, L; Ghelis, N. J. Am. Chem. Soc. 1963, 85, 1337.
38. Incomplete carbon combustion in high MW materials with high unsaturated carbon content is a commonly observed property. See reference 8 and (a) Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1991, 113, 7411. (b) Stephens, E. B.; Tour, J. M. Macromolecules 1993, 26, 2420.
39. Incomplete carbon combustion in high MW materials with high unsaturated carbon content is a commonly observed property. See reference 8 and (a) Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1991, 113, 7411. (b) Stephens, E. B.; Tour, J. M. Macromolecules 1993, 26, 2420.