Synthesis and testing of new end-functionalized oligomers for molecular electronics

Tetrahedron

Volumn 59, Issue 43, 2003, Pages 8555-8570

  Flatt, Austen K ^a   Dirk, Shawn M ^a   Henderson, Jay C ^a   Shen, Dwanleen E ^a   Su, Jie ^b   Reed, Mark A ^b   Tour, James M ^a  

^a RICE UNIVERSITY   (United States)

^b YALE UNIVERSITY   (United States)

Author keywords

Molecular electronics; Oligomers

Indexed keywords

BENZENE DERIVATIVE; CHEMICAL COMPOUND; ETHYLENE DERIVATIVE; OLIGOMER; PYRIDINE DERIVATIVE; THIOL DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL INTERACTION; ELECTROCHEMISTRY; ELECTRONICS; IONIZING RADIATION; MOLECULAR DYNAMICS; MOLECULE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; SYNTHESIS; TEMPERATURE;

EID: 0141594835     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.09.004     Document Type: Article

References (45)

1. Tour J.M. Molecular Electronics: Commercial Insights, Chemistry, Devices, Architecture and Programming. 2003;World Scientific, New Jersey.
2. For recent reviews see: (a) Tour J.M. Acc. Chem. Res. 33:2000;791-804 (b) Tour J.M., Rawlett A.M., Kozaki M., Yao Y., Jagessar C., Dirk S.M., Price D.W., Reed M.A., Zhou C.-W., Chen J., Wang W., Campbell I. Chem. Eur. J. 7:2001;5118 (c) Reed M.A., Tour J.M. Sci. Am. 2000;86.
3. For recent reviews see: (a) Tour J.M. Acc. Chem. Res. 33:2000;791-804 (b) Tour J.M., Rawlett A.M., Kozaki M., Yao Y., Jagessar C., Dirk S.M., Price D.W., Reed M.A., Zhou C.-W., Chen J., Wang W., Campbell I. Chem. Eur. J. 7:2001;5118 (c) Reed M.A., Tour J.M. Sci. Am. 2000;86.
4. For recent reviews see: (a) Tour J.M. Acc. Chem. Res. 33:2000;791-804 (b) Tour J.M., Rawlett A.M., Kozaki M., Yao Y., Jagessar C., Dirk S.M., Price D.W., Reed M.A., Zhou C.-W., Chen J., Wang W., Campbell I. Chem. Eur. J. 7:2001;5118 (c) Reed M.A., Tour J.M. Sci. Am. 2000;86.
5. Chen J., Reed M.A., Rawlett A.M., Tour J.M. Science. 286:1999;1550-1552.
6. Chen J., Wang W., Reed M.A., Rawlett A.M., Tour J.M. Appl. Phys. Lett. 286:2000;1224-1226.
7. Chen J., Wang W., Reed M.A., Rawlett A.M., Price D.W., Tour J.M. Mater. Res. Soc. Symp. Proc. 582:2001;H321-H325.
8. Hwang J.-J., Tour J.M. Tetrahedron. 58:2002;10387-10405.
9. Dirk S.M., Tour J.M. Tetrahedron. 2003;287-293.
10. Price D.W., Dirk S.M., Maya F., Tour J.M. Tetrahedron. 59:2003;2497-2518.
11. Price D.W. Jr., Tour J.M. Tetrahedron. 59:2003;3131-3156.
12. Sikes H.D., Smalley J.F., Dudek S.P., Cook A.R., Newton M.D., Chidsey C.E.D., Feldberg S.W. Science. 291:2001;1519-1523.
13. Price, D. W.; Dirk, S. M.; Rawlett, A. M.; Chen, J.; Wang, W.; Reed, M. A.; Zacarias, A. G.; Tour, J. M. Mater. Res. Soc. Symp. Proc. 2001, 660, JJ9.4.1/D7.4.1-JJ.9.4.9/D7.4.9.
14. Seminario J.M., Zacarias A.G., Tour J.M. J. Am. Chem. Soc. 122:2000;3015-3020.
15. Ramachandran G.K., Hopson T.J., Rawlett A.M., Nagahara L.A., Primak A., Lindsay S.M. Science. 300:2003;1413-1416.
16. Donhauser Z.J., Mantooth B.A., Pearl T.P., Kelly K.F., Sanjini U.A., Weiss P.S. Jpn J. Appl. Phys. 41:2002;4871-4877.
17. Asano T., Furuta H., Hofmann H.-J., Cimiraglia R., Tsuno Y., Fujio M. J. Org. Chem. 58:1993;4418-4423.
18. Noureldin N.A., Bellegarde J.W. Synthesis. 6:1999;939-942.
19. Pearson D.L., Tour J.M. J. Org. Chem. 62:1997;1376-1387.
20. Orito K., Hatakeyama T., Takeo M., Uchiito S., Tokuda M., Suginome H. Tetrahedron. 54:1998;8403-8410.
21. Seminario J.M., Zacarias A.G., Tour J.M. J. Am. Chem. Soc. 121:1999;411-416.
22. For reviews see: (a) Fanta P.E. Synthesis. 1974;9 (b) Goshaev M., Otroshchenko O.S., Sadykov A.S. Russ. Chem. Rev. 41:1972;1046.
23. For reviews see: (a) Fanta P.E. Synthesis. 1974;9 (b) Goshaev M., Otroshchenko O.S., Sadykov A.S. Russ. Chem. Rev. 41:1972;1046.
24. Matsuda K., Yanagisawa I., Isomura Y., Mase T., Shibanuma T. Synth. Commun. 27:1997;2393-2402.
25. (a) Romero F.M., Ziessel R. Tetrahedron Lett. 36:1995;6471-6474.
26. (b) Benin V., Kaszynski P., Pink M., Young V.G. Jr. J. Org. Chem. 65:2000;6388-6397.
27. Wu J., Chi C., Wang X., Li J., Zhao X., Wang F. Synth. Commun. 30:2000;4293-4298.
28. (a) Petrow S. J. Chem. Soc. 1948;1389-1392.
29. (b) Zasshi Y. Chem. Abstr. 1959;1129-1132.
30. Case F.H. J. Am. Chem. Soc. 68:1946;2574-2577.
31. Kushmerick J.G., Holt D.B., Pollack S.K., Ratner M.A., Yang J.C., Schull T.L., Naciri J., Moore M.H., Shashidhar R. J. Am. Chem. Soc. 124:2002;10654-10655.
32. Overberger C.G., Lebovits A. J. Am. Chem. Soc. 78:1956;4792-4797.
33. Seyferth D., Stone F.G.A. J. Am. Chem. Soc. 79:1957;515-517.
34. Stille J.K. Angew. Chem., Int. Ed. Engl. 25:1986;508.
35. For a review see Beletskaya I.P., Cheprakov A.V. Chem. Rev. 100:2000;3009-3066.
36. Yu C.J., Chong Y., Kayyem J.F., Gozin M. J. Org. Chem. 64:1999;2070-2079.
37. Detert H., Sugiono E. Synth. Met. 115:2000;89-92.
38. Wong M.S., Li Z.H., Shek M.F., Samoc M., Samoc A., Luther-Davies B. Chem. Mater. 14:2002;2999-3004.
39. Syamakumari A., Schenning A.P.H.J., Meijer E.W. Chem. Eur. J. 8:2002;3353-3361.
40. Gu T., Ceroni P., Marconi G., Armaroli N., Nierengarten J.-F. J. Org. Chem. 66:2001;6432-6439.
41. Kushmerick J.G., Holt D.B., Pollack S.K., Ratner M.A., Yang J.C., Schull T.L., Naciri J., Moore M.H., Shashidhar R. J. Am. Chem. Soc. 124:2002;10654-10655.
42. Reed M.A., Chen J., Rawlett A.M., Price D.W., Tour J.M. Appl. Phys. Lett. 78:2001;3735-3737.
43. Sonogashira K., Tohda Y., Hagihara N. Tetrahedron Lett. 1975;4467.
44. Dougherty T.K., Lau K.S.Y., Hedberg F.L. J. Org. Chem. 48:1983;5273-5280.
45. Kosynkin D.V., Tour J.M. Org. Lett. 3:2001;993-995.