Potential molecular wires and molecular alligator clips

Nanotechnology

Volumn 7, Issue 4, 1996, Pages 430-433

  Schumm, Jeffry S ^a   Pearson, Darren L ^a   Jones II, LeRoy ^a   Hara, Ryuichiro ^a   Tour, James M ^a  

^a UNIVERSITY OF SOUTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ITERATIVE METHODS; MASS SPECTROMETRY; MOLECULES; OPTICAL PROPERTIES; SEMICONDUCTOR QUANTUM WIRES; SPECTROSCOPY; SYNTHESIS (CHEMICAL);

CLOSE COUPLING; IODINATION; MOLECULAR ALLIGATOR CLIPS; MOLECULAR WIRES; OPTICAL ABSORBANCE SATURATION; PHOTODESILYLATION;

OLIGOMERS;

EID: 0030365657     PISSN: 09574484     EISSN: None     Source Type: Journal    
DOI: 10.1088/0957-4484/7/4/023     Document Type: Article

References (36)

1. (a) Aviram A (ed) 1992 Molecular Electronics: Science and Technology Confer. Proc. No. 262 (New York: American Institute of Physics)
2. (b) Miller JS 1990 Adv. Mater. 2 378
3. (c) Waldeck D H and Beratan DN 1993 Science 261 576
4. (d) Guay J, Diaz A, Wu R and Tour J M 1993 J. Am. Chem. Soc. 115 1869
5. (a) Reed MA 1993 Yale University, personal communication
6. (b) Kirk W P and Reed M A (ed) 1992 Nanostructures and Mesoscopic Systems (San Diego: Academic)
7. Miller J S 1990 Adv. Mater. 2 495, 601
8. For a presentation of some fundamental work in the area of potential molecular wires, see: (a) Kenny P W and Miller L L 1988 J. Chem. Soc., Chem. Commun. 85 (b) Kugimiya S-i, Lazrak T, Blanchard-Desce M and Lehn J-M 1991 J. Chem. Soc., Chem. Commun. 1179 (c) Crossley M J and Burn PL 1991 J. Chem. Soc. Chem. Commun. 1569 (d) Zecevic S, Simic-Glavaski B and Yeager E 1985 J. Electroanal. Chem. 196 339 (e) Yoshimura T, Tatsuura S, Sotoyama W, Matsuura A and Hayano T 1992 Appl. Phys. Lett. 60 268 (f) Sessler J L, Capuano V L and Harriman A 1993 J. Am. Chem. Soc. 115 4618 (g) Tachibana H, Azumi R, Nakamura T, Matsumoto M and Kawabata Y 1992 Chem. Lett. 173 (h) O'Neil M P, Niemczyk M P, Svec W A, Gosztola D, Gaines III G L and Wasielewski M R 1992 Science 257 63 (i) Wudl F and Bitler SP 1986 J. Am. Chem. Soc. 108 4685 (j) Lu F-L, Wudl F, Nowak M and Heeger AJ 1986 J. Am. Chem. Soc. 108 8311
9. For a presentation of some fundamental work in the area of potential molecular wires, see: (a) Kenny P W and Miller L L 1988 J. Chem. Soc., Chem. Commun. 85 (b) Kugimiya S-i, Lazrak T, Blanchard-Desce M and Lehn J-M 1991 J. Chem. Soc., Chem. Commun. 1179 (c) Crossley M J and Burn PL 1991 J. Chem. Soc. Chem. Commun. 1569 (d) Zecevic S, Simic-Glavaski B and Yeager E 1985 J. Electroanal. Chem. 196 339 (e) Yoshimura T, Tatsuura S, Sotoyama W, Matsuura A and Hayano T 1992 Appl. Phys. Lett. 60 268 (f) Sessler J L, Capuano V L and Harriman A 1993 J. Am. Chem. Soc. 115 4618 (g) Tachibana H, Azumi R, Nakamura T, Matsumoto M and Kawabata Y 1992 Chem. Lett. 173 (h) O'Neil M P, Niemczyk M P, Svec W A, Gosztola D, Gaines III G L and Wasielewski M R 1992 Science 257 63 (i) Wudl F and Bitler SP 1986 J. Am. Chem. Soc. 108 4685 (j) Lu F-L, Wudl F, Nowak M and Heeger AJ 1986 J. Am. Chem. Soc. 108 8311
10. For a presentation of some fundamental work in the area of potential molecular wires, see: (a) Kenny P W and Miller L L 1988 J. Chem. Soc., Chem. Commun. 85 (b) Kugimiya S-i, Lazrak T, Blanchard-Desce M and Lehn J-M 1991 J. Chem. Soc., Chem. Commun. 1179 (c) Crossley M J and Burn PL 1991 J. Chem. Soc. Chem. Commun. 1569 (d) Zecevic S, Simic-Glavaski B and Yeager E 1985 J. Electroanal. Chem. 196 339 (e) Yoshimura T, Tatsuura S, Sotoyama W, Matsuura A and Hayano T 1992 Appl. Phys. Lett. 60 268 (f) Sessler J L, Capuano V L and Harriman A 1993 J. Am. Chem. Soc. 115 4618 (g) Tachibana H, Azumi R, Nakamura T, Matsumoto M and Kawabata Y 1992 Chem. Lett. 173 (h) O'Neil M P, Niemczyk M P, Svec W A, Gosztola D, Gaines III G L and Wasielewski M R 1992 Science 257 63 (i) Wudl F and Bitler SP 1986 J. Am. Chem. Soc. 108 4685 (j) Lu F-L, Wudl F, Nowak M and Heeger AJ 1986 J. Am. Chem. Soc. 108 8311
11. For a presentation of some fundamental work in the area of potential molecular wires, see: (a) Kenny P W and Miller L L 1988 J. Chem. Soc., Chem. Commun. 85 (b) Kugimiya S-i, Lazrak T, Blanchard-Desce M and Lehn J-M 1991 J. Chem. Soc., Chem. Commun. 1179 (c) Crossley M J and Burn PL 1991 J. Chem. Soc. Chem. Commun. 1569 (d) Zecevic S, Simic-Glavaski B and Yeager E 1985 J. Electroanal. Chem. 196 339 (e) Yoshimura T, Tatsuura S, Sotoyama W, Matsuura A and Hayano T 1992 Appl. Phys. Lett. 60 268 (f) Sessler J L, Capuano V L and Harriman A 1993 J. Am. Chem. Soc. 115 4618 (g) Tachibana H, Azumi R, Nakamura T, Matsumoto M and Kawabata Y 1992 Chem. Lett. 173 (h) O'Neil M P, Niemczyk M P, Svec W A, Gosztola D, Gaines III G L and Wasielewski M R 1992 Science 257 63 (i) Wudl F and Bitler SP 1986 J. Am. Chem. Soc. 108 4685 (j) Lu F-L, Wudl F, Nowak M and Heeger AJ 1986 J. Am. Chem. Soc. 108 8311
12. For a presentation of some fundamental work in the area of potential molecular wires, see: (a) Kenny P W and Miller L L 1988 J. Chem. Soc., Chem. Commun. 85 (b) Kugimiya S-i, Lazrak T, Blanchard-Desce M and Lehn J-M 1991 J. Chem. Soc., Chem. Commun. 1179 (c) Crossley M J and Burn PL 1991 J. Chem. Soc. Chem. Commun. 1569 (d) Zecevic S, Simic-Glavaski B and Yeager E 1985 J. Electroanal. Chem. 196 339 (e) Yoshimura T, Tatsuura S, Sotoyama W, Matsuura A and Hayano T 1992 Appl. Phys. Lett. 60 268 (f) Sessler J L, Capuano V L and Harriman A 1993 J. Am. Chem. Soc. 115 4618 (g) Tachibana H, Azumi R, Nakamura T, Matsumoto M and Kawabata Y 1992 Chem. Lett. 173 (h) O'Neil M P, Niemczyk M P, Svec W A, Gosztola D, Gaines III G L and Wasielewski M R 1992 Science 257 63 (i) Wudl F and Bitler SP 1986 J. Am. Chem. Soc. 108 4685 (j) Lu F-L, Wudl F, Nowak M and Heeger AJ 1986 J. Am. Chem. Soc. 108 8311
13. For a presentation of some fundamental work in the area of potential molecular wires, see: (a) Kenny P W and Miller L L 1988 J. Chem. Soc., Chem. Commun. 85 (b) Kugimiya S-i, Lazrak T, Blanchard-Desce M and Lehn J-M 1991 J. Chem. Soc., Chem. Commun. 1179 (c) Crossley M J and Burn PL 1991 J. Chem. Soc. Chem. Commun. 1569 (d) Zecevic S, Simic-Glavaski B and Yeager E 1985 J. Electroanal. Chem. 196 339 (e) Yoshimura T, Tatsuura S, Sotoyama W, Matsuura A and Hayano T 1992 Appl. Phys. Lett. 60 268 (f) Sessler J L, Capuano V L and Harriman A 1993 J. Am. Chem. Soc. 115 4618 (g) Tachibana H, Azumi R, Nakamura T, Matsumoto M and Kawabata Y 1992 Chem. Lett. 173 (h) O'Neil M P, Niemczyk M P, Svec W A, Gosztola D, Gaines III G L and Wasielewski M R 1992 Science 257 63 (i) Wudl F and Bitler SP 1986 J. Am. Chem. Soc. 108 4685 (j) Lu F-L, Wudl F, Nowak M and Heeger AJ 1986 J. Am. Chem. Soc. 108 8311
14. For a presentation of some fundamental work in the area of potential molecular wires, see: (a) Kenny P W and Miller L L 1988 J. Chem. Soc., Chem. Commun. 85 (b) Kugimiya S-i, Lazrak T, Blanchard-Desce M and Lehn J-M 1991 J. Chem. Soc., Chem. Commun. 1179 (c) Crossley M J and Burn PL 1991 J. Chem. Soc. Chem. Commun. 1569 (d) Zecevic S, Simic-Glavaski B and Yeager E 1985 J. Electroanal. Chem. 196 339 (e) Yoshimura T, Tatsuura S, Sotoyama W, Matsuura A and Hayano T 1992 Appl. Phys. Lett. 60 268 (f) Sessler J L, Capuano V L and Harriman A 1993 J. Am. Chem. Soc. 115 4618 (g) Tachibana H, Azumi R, Nakamura T, Matsumoto M and Kawabata Y 1992 Chem. Lett. 173 (h) O'Neil M P, Niemczyk M P, Svec W A, Gosztola D, Gaines III G L and Wasielewski M R 1992 Science 257 63 (i) Wudl F and Bitler SP 1986 J. Am. Chem. Soc. 108 4685 (j) Lu F-L, Wudl F, Nowak M and Heeger AJ 1986 J. Am. Chem. Soc. 108 8311
15. For a presentation of some fundamental work in the area of potential molecular wires, see: (a) Kenny P W and Miller L L 1988 J. Chem. Soc., Chem. Commun. 85 (b) Kugimiya S-i, Lazrak T, Blanchard-Desce M and Lehn J-M 1991 J. Chem. Soc., Chem. Commun. 1179 (c) Crossley M J and Burn PL 1991 J. Chem. Soc. Chem. Commun. 1569 (d) Zecevic S, Simic-Glavaski B and Yeager E 1985 J. Electroanal. Chem. 196 339 (e) Yoshimura T, Tatsuura S, Sotoyama W, Matsuura A and Hayano T 1992 Appl. Phys. Lett. 60 268 (f) Sessler J L, Capuano V L and Harriman A 1993 J. Am. Chem. Soc. 115 4618 (g) Tachibana H, Azumi R, Nakamura T, Matsumoto M and Kawabata Y 1992 Chem. Lett. 173 (h) O'Neil M P, Niemczyk M P, Svec W A, Gosztola D, Gaines III G L and Wasielewski M R 1992 Science 257 63 (i) Wudl F and Bitler SP 1986 J. Am. Chem. Soc. 108 4685 (j) Lu F-L, Wudl F, Nowak M and Heeger AJ 1986 J. Am. Chem. Soc. 108 8311
16. For a presentation of some fundamental work in the area of potential molecular wires, see: (a) Kenny P W and Miller L L 1988 J. Chem. Soc., Chem. Commun. 85 (b) Kugimiya S-i, Lazrak T, Blanchard-Desce M and Lehn J-M 1991 J. Chem. Soc., Chem. Commun. 1179 (c) Crossley M J and Burn PL 1991 J. Chem. Soc. Chem. Commun. 1569 (d) Zecevic S, Simic-Glavaski B and Yeager E 1985 J. Electroanal. Chem. 196 339 (e) Yoshimura T, Tatsuura S, Sotoyama W, Matsuura A and Hayano T 1992 Appl. Phys. Lett. 60 268 (f) Sessler J L, Capuano V L and Harriman A 1993 J. Am. Chem. Soc. 115 4618 (g) Tachibana H, Azumi R, Nakamura T, Matsumoto M and Kawabata Y 1992 Chem. Lett. 173 (h) O'Neil M P, Niemczyk M P, Svec W A, Gosztola D, Gaines III G L and Wasielewski M R 1992 Science 257 63 (i) Wudl F and Bitler SP 1986 J. Am. Chem. Soc. 108 4685 (j) Lu F-L, Wudl F, Nowak M and Heeger AJ 1986 J. Am. Chem. Soc. 108 8311
17. For a presentation of some fundamental work in the area of potential molecular wires, see: (a) Kenny P W and Miller L L 1988 J. Chem. Soc., Chem. Commun. 85 (b) Kugimiya S-i, Lazrak T, Blanchard-Desce M and Lehn J-M 1991 J. Chem. Soc., Chem. Commun. 1179 (c) Crossley M J and Burn PL 1991 J. Chem. Soc. Chem. Commun. 1569 (d) Zecevic S, Simic-Glavaski B and Yeager E 1985 J. Electroanal. Chem. 196 339 (e) Yoshimura T, Tatsuura S, Sotoyama W, Matsuura A and Hayano T 1992 Appl. Phys. Lett. 60 268 (f) Sessler J L, Capuano V L and Harriman A 1993 J. Am. Chem. Soc. 115 4618 (g) Tachibana H, Azumi R, Nakamura T, Matsumoto M and Kawabata Y 1992 Chem. Lett. 173 (h) O'Neil M P, Niemczyk M P, Svec W A, Gosztola D, Gaines III G L and Wasielewski M R 1992 Science 257 63 (i) Wudl F and Bitler SP 1986 J. Am. Chem. Soc. 108 4685 (j) Lu F-L, Wudl F, Nowak M and Heeger AJ 1986 J. Am. Chem. Soc. 108 8311
18. An iterative doubling approach was first described by Whiting and then later used by Moore to prepare oligo(1,3-phenylene-ethynylenes). See: (a) Igner E, Paynter O I, Simmonds D J and Whiting M C 1987 J. Chem. Soc., Perkin Trans, 1 2447 (b) Bidd I, Kelly D J, Ottley P M, Paynter O I, Simmonds D J and Whiting M C 1983 J. Chem. Soc., Perkin Trans, 1 1369 (c) Zhang J, Moore J S, Xu Z and Aguirre RA 1992 J. Am. Chem. Soc. 114 2273 (d) Xu Z and Moore J S 1993 Angew. Chem. Int. Ed. Engl. 32 1354 For related oligomers and polymers, see: (e) Grubbs R H and Kratz D 1993 Chem. Ber. 126 149 (f) Scherf U and Müllen K 1992 Synthesis 23
19. An iterative doubling approach was first described by Whiting and then later used by Moore to prepare oligo(1,3-phenylene-ethynylenes). See: (a) Igner E, Paynter O I, Simmonds D J and Whiting M C 1987 J. Chem. Soc., Perkin Trans, 1 2447 (b) Bidd I, Kelly D J, Ottley P M, Paynter O I, Simmonds D J and Whiting M C 1983 J. Chem. Soc., Perkin Trans, 1 1369 (c) Zhang J, Moore J S, Xu Z and Aguirre RA 1992 J. Am. Chem. Soc. 114 2273 (d) Xu Z and Moore J S 1993 Angew. Chem. Int. Ed. Engl. 32 1354 For related oligomers and polymers, see: (e) Grubbs R H and Kratz D 1993 Chem. Ber. 126 149 (f) Scherf U and Müllen K 1992 Synthesis 23
20. An iterative doubling approach was first described by Whiting and then later used by Moore to prepare oligo(1,3-phenylene-ethynylenes). See: (a) Igner E, Paynter O I, Simmonds D J and Whiting M C 1987 J. Chem. Soc., Perkin Trans, 1 2447 (b) Bidd I, Kelly D J, Ottley P M, Paynter O I, Simmonds D J and Whiting M C 1983 J. Chem. Soc., Perkin Trans, 1 1369 (c) Zhang J, Moore J S, Xu Z and Aguirre RA 1992 J. Am. Chem. Soc. 114 2273 (d) Xu Z and Moore J S 1993 Angew. Chem. Int. Ed. Engl. 32 1354 For related oligomers and polymers, see: (e) Grubbs R H and Kratz D 1993 Chem. Ber. 126 149 (f) Scherf U and Müllen K 1992 Synthesis 23
21. An iterative doubling approach was first described by Whiting and then later used by Moore to prepare oligo(1,3-phenylene-ethynylenes). See: (a) Igner E, Paynter O I, Simmonds D J and Whiting M C 1987 J. Chem. Soc., Perkin Trans, 1 2447 (b) Bidd I, Kelly D J, Ottley P M, Paynter O I, Simmonds D J and Whiting M C 1983 J. Chem. Soc., Perkin Trans, 1 1369 (c) Zhang J, Moore J S, Xu Z and Aguirre RA 1992 J. Am. Chem. Soc. 114 2273 (d) Xu Z and Moore J S 1993 Angew. Chem. Int. Ed. Engl. 32 1354 For related oligomers and polymers, see: (e) Grubbs R H and Kratz D 1993 Chem. Ber. 126 149 (f) Scherf U and Müllen K 1992 Synthesis 23
22. An iterative doubling approach was first described by Whiting and then later used by Moore to prepare oligo(1,3-phenylene-ethynylenes). See: (a) Igner E, Paynter O I, Simmonds D J and Whiting M C 1987 J. Chem. Soc., Perkin Trans, 1 2447 (b) Bidd I, Kelly D J, Ottley P M, Paynter O I, Simmonds D J and Whiting M C 1983 J. Chem. Soc., Perkin Trans, 1 1369 (c) Zhang J, Moore J S, Xu Z and Aguirre RA 1992 J. Am. Chem. Soc. 114 2273 (d) Xu Z and Moore J S 1993 Angew. Chem. Int. Ed. Engl. 32 1354 For related oligomers and polymers, see: (e) Grubbs R H and Kratz D 1993 Chem. Ber. 126 149 (f) Scherf U and Müllen K 1992 Synthesis 23
23. An iterative doubling approach was first described by Whiting and then later used by Moore to prepare oligo(1,3-phenylene-ethynylenes). See: (a) Igner E, Paynter O I, Simmonds D J and Whiting M C 1987 J. Chem. Soc., Perkin Trans, 1 2447 (b) Bidd I, Kelly D J, Ottley P M, Paynter O I, Simmonds D J and Whiting M C 1983 J. Chem. Soc., Perkin Trans, 1 1369 (c) Zhang J, Moore J S, Xu Z and Aguirre RA 1992 J. Am. Chem. Soc. 114 2273 (d) Xu Z and Moore J S 1993 Angew. Chem. Int. Ed. Engl. 32 1354 For related oligomers and polymers, see: (e) Grubbs R H and Kratz D 1993 Chem. Ber. 126 149 (f) Scherf U and Müllen K 1992 Synthesis 23
24. (a) Guay J, Diaz A, Wu R, Tour J M and Dao L H 1992 Chem. Mater. 4 254
25. (b) Tour J M and Wu R 1992 Macromolecules 25 1901
26. (c) Guay J, Kasai P, Diaz A, Wu R, Tour J M and Dao L H 1992 Chem. Mater. 4 1097
27. (d) Skotheim T A (ed) 1986 Handbook of Conducting Polymers (New York: Dekker)
28. (a) Abbott N L, Folkers J P and Whitesides G M 1992 Science 257 1380
29. (b) Charych D H and Bednarski MD 1992 Mater. Res. Soc. Bull. 17(11) 61
30. For the conversion of a methyl ketone to an alkyne, see: Negishi E, King A O and Tour J M 1985 Org. Synth. 64 44
31. For the iodination procedure, see: (a) Moore J S, Weinstein E J and Wu Z 1991 Tetrahedron Lett. 32 2465 For the cross coupling procedure, see: (b) Sonogashira K, Tohda Y and Hagihara N 1975 Tetrahedron Lett. 4467 (c) Stephens R D and Castro CE 1963 J. Org. Chem. 28 3313 (d) Suffert J and Ziessel R 1991 Tetrahedron Lett. 32 757
32. For the iodination procedure, see: (a) Moore J S, Weinstein E J and Wu Z 1991 Tetrahedron Lett. 32 2465 For the cross coupling procedure, see: (b) Sonogashira K, Tohda Y and Hagihara N 1975 Tetrahedron Lett. 4467 (c) Stephens R D and Castro CE 1963 J. Org. Chem. 28 3313 (d) Suffert J and Ziessel R 1991 Tetrahedron Lett. 32 757
33. For the iodination procedure, see: (a) Moore J S, Weinstein E J and Wu Z 1991 Tetrahedron Lett. 32 2465 For the cross coupling procedure, see: (b) Sonogashira K, Tohda Y and Hagihara N 1975 Tetrahedron Lett. 4467 (c) Stephens R D and Castro CE 1963 J. Org. Chem. 28 3313 (d) Suffert J and Ziessel R 1991 Tetrahedron Lett. 32 757
34. For the iodination procedure, see: (a) Moore J S, Weinstein E J and Wu Z 1991 Tetrahedron Lett. 32 2465 For the cross coupling procedure, see: (b) Sonogashira K, Tohda Y and Hagihara N 1975 Tetrahedron Lett. 4467 (c) Stephens R D and Castro CE 1963 J. Org. Chem. 28 3313 (d) Suffert J and Ziessel R 1991 Tetrahedron Lett. 32 757
35. Doyle M P and Bryker W J 1979 J. Org. Chem. 44 1572
36. Pearson D L, Schumm J S and Tour JM 1994 Macromolecules 27 2348