Rapid Syntheses of Oligo(2,5-thiophene ethynylene)s with Thioester Termini: Potential Molecular Scale Wires with Alligator Clips

Journal of Organic Chemistry

Volumn 62, Issue 5, 1997, Pages 1376-1387

  Pearson, Darren L ^a   Tour, James M ^a  

^a UNIVERSITY OF SOUTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000992211     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962335y     Document Type: Article

References (49)

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9. For some recent background work on the formation of molecular-based transporters and devices, see: (a) Grosshenny, V.; Harriman, A.; Ziessel R. Angew. Chem., Int. Ed. Engl. 1995, 34, 1100. (b) Langler, L.; Stockman, L.; Heremans, J. P.; Bayor, V.; Oik, C. H.; Van Haesendonck, C.; Bruynseraede, Y.; Issi, J.-P. Synth. Met. 1995, 70, 1393. Pascual, J. I.; Méndez, J.; Gómez-Herrero, J.; Baró, A. M.; Garcia, N.; Landman, U.; Luedtker, W. D.; Bogachek, E. N.; Cheng, H.-P. Science 1995, 267, 1793. Purcell, S. T.; Garcia, N.; Binh, V. T.; Jones, L., II; Tour, J. M. J. Am. Chem. Soc. 1994, 116, 11985. (e) Martin, C. R. Science 1994, 266, 1961. (f) Seth, J.; Palaniappan, V.; Johnson, T. E.; Prathapan, S.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1994, 116, 10578. (g) Gust, D. Nature 1994, 372, 133. (h) Wu, C.; Bein, T. Science 1994, 266, 1013. Wagner, R. W.; Lindsey, J. S.; Seth, J.; Palaniappan, V.; Bocain, D. F. J. Am. Chem. Soc. 1996, 118, 3996. (j) Sailor, M. J.; Curtis, C. L. Adv. Mater. 1994, 6, 688. (k) Brigelletti, F.; Flamigni, L.; Balzani, V.; Collin, J.; Sauvage, J.; Sour, A.; Constable, E. C.; Thompson, A. M. W. C. J. Am. Chem. Soc. 1994, 116, 7692. Wu, C.; Bein, T. Science 1994, 264, 1757. Moeroer, W. E. Science 1994, 265, 46. (n) Sessler J. L.; Capuano, V. L.; Harriman, A. J. Am. Chem. Soc. 1993, 115, 4618. (o) Farazdel, A.; Dupuis, M.; Clementi, E.; Aviram. A. J. Am. Chem. Soc. 1990, 112, 4206. (p) Tour, J. M.; Wu, R.; Schumm, J. S. J. Am. Chem. Soc. 1991, 113, 7064. (q) Dai, H.; Wong, E. W.; Lieber, C. M. Science 1996, 272, 523. (r) Wu, R.; Schumm, J. S.; Pearson, D. L.; Tour, J. M. J. Org. Chem. 1996, 61, 6906. (s) Ward, M. D. Chem. Ind. 1996, 569.
10. For some recent background work on the formation of molecular-based transporters and devices, see: (a) Grosshenny, V.; Harriman, A.; Ziessel R. Angew. Chem., Int. Ed. Engl. 1995, 34, 1100. (b) Langler, L.; Stockman, L.; Heremans, J. P.; Bayor, V.; Oik, C. H.; Van Haesendonck, C.; Bruynseraede, Y.; Issi, J.-P. Synth. Met. 1995, 70, 1393. Pascual, J. I.; Méndez, J.; Gómez-Herrero, J.; Baró, A. M.; Garcia, N.; Landman, U.; Luedtker, W. D.; Bogachek, E. N.; Cheng, H.-P. Science 1995, 267, 1793. Purcell, S. T.; Garcia, N.; Binh, V. T.; Jones, L., II; Tour, J. M. J. Am. Chem. Soc. 1994, 116, 11985. (e) Martin, C. R. Science 1994, 266, 1961. (f) Seth, J.; Palaniappan, V.; Johnson, T. E.; Prathapan, S.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1994, 116, 10578. (g) Gust, D. Nature 1994, 372, 133. (h) Wu, C.; Bein, T. Science 1994, 266, 1013. Wagner, R. W.; Lindsey, J. S.; Seth, J.; Palaniappan, V.; Bocain, D. F. J. Am. Chem. Soc. 1996, 118, 3996. (j) Sailor, M. J.; Curtis, C. L. Adv. Mater. 1994, 6, 688. (k) Brigelletti, F.; Flamigni, L.; Balzani, V.; Collin, J.; Sauvage, J.; Sour, A.; Constable, E. C.; Thompson, A. M. W. C. J. Am. Chem. Soc. 1994, 116, 7692. Wu, C.; Bein, T. Science 1994, 264, 1757. Moeroer, W. E. Science 1994, 265, 46. (n) Sessler J. L.; Capuano, V. L.; Harriman, A. J. Am. Chem. Soc. 1993, 115, 4618. (o) Farazdel, A.; Dupuis, M.; Clementi, E.; Aviram. A. J. Am. Chem. Soc. 1990, 112, 4206. (p) Tour, J. M.; Wu, R.; Schumm, J. S. J. Am. Chem. Soc. 1991, 113, 7064. (q) Dai, H.; Wong, E. W.; Lieber, C. M. Science 1996, 272, 523. (r) Wu, R.; Schumm, J. S.; Pearson, D. L.; Tour, J. M. J. Org. Chem. 1996, 61, 6906. (s) Ward, M. D. Chem. Ind. 1996, 569.
11. For some recent background work on the formation of molecular-based transporters and devices, see: (a) Grosshenny, V.; Harriman, A.; Ziessel R. Angew. Chem., Int. Ed. Engl. 1995, 34, 1100. (b) Langler, L.; Stockman, L.; Heremans, J. P.; Bayor, V.; Oik, C. H.; Van Haesendonck, C.; Bruynseraede, Y.; Issi, J.-P. Synth. Met. 1995, 70, 1393. Pascual, J. I.; Méndez, J.; Gómez-Herrero, J.; Baró, A. M.; Garcia, N.; Landman, U.; Luedtker, W. D.; Bogachek, E. N.; Cheng, H.-P. Science 1995, 267, 1793. Purcell, S. T.; Garcia, N.; Binh, V. T.; Jones, L., II; Tour, J. M. J. Am. Chem. Soc. 1994, 116, 11985. (e) Martin, C. R. Science 1994, 266, 1961. (f) Seth, J.; Palaniappan, V.; Johnson, T. E.; Prathapan, S.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1994, 116, 10578. (g) Gust, D. Nature 1994, 372, 133. (h) Wu, C.; Bein, T. Science 1994, 266, 1013. Wagner, R. W.; Lindsey, J. S.; Seth, J.; Palaniappan, V.; Bocain, D. F. J. Am. Chem. Soc. 1996, 118, 3996. (j) Sailor, M. J.; Curtis, C. L. Adv. Mater. 1994, 6, 688. (k) Brigelletti, F.; Flamigni, L.; Balzani, V.; Collin, J.; Sauvage, J.; Sour, A.; Constable, E. C.; Thompson, A. M. W. C. J. Am. Chem. Soc. 1994, 116, 7692. Wu, C.; Bein, T. Science 1994, 264, 1757. Moeroer, W. E. Science 1994, 265, 46. (n) Sessler J. L.; Capuano, V. L.; Harriman, A. J. Am. Chem. Soc. 1993, 115, 4618. (o) Farazdel, A.; Dupuis, M.; Clementi, E.; Aviram. A. J. Am. Chem. Soc. 1990, 112, 4206. (p) Tour, J. M.; Wu, R.; Schumm, J. S. J. Am. Chem. Soc. 1991, 113, 7064. (q) Dai, H.; Wong, E. W.; Lieber, C. M. Science 1996, 272, 523. (r) Wu, R.; Schumm, J. S.; Pearson, D. L.; Tour, J. M. J. Org. Chem. 1996, 61, 6906. (s) Ward, M. D. Chem. Ind. 1996, 569.
12. For some recent background work on the formation of molecular-based transporters and devices, see: (a) Grosshenny, V.; Harriman, A.; Ziessel R. Angew. Chem., Int. Ed. Engl. 1995, 34, 1100. (b) Langler, L.; Stockman, L.; Heremans, J. P.; Bayor, V.; Oik, C. H.; Van Haesendonck, C.; Bruynseraede, Y.; Issi, J.-P. Synth. Met. 1995, 70, 1393. Pascual, J. I.; Méndez, J.; Gómez-Herrero, J.; Baró, A. M.; Garcia, N.; Landman, U.; Luedtker, W. D.; Bogachek, E. N.; Cheng, H.-P. Science 1995, 267, 1793. Purcell, S. T.; Garcia, N.; Binh, V. T.; Jones, L., II; Tour, J. M. J. Am. Chem. Soc. 1994, 116, 11985. (e) Martin, C. R. Science 1994, 266, 1961. (f) Seth, J.; Palaniappan, V.; Johnson, T. E.; Prathapan, S.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1994, 116, 10578. (g) Gust, D. Nature 1994, 372, 133. (h) Wu, C.; Bein, T. Science 1994, 266, 1013. Wagner, R. W.; Lindsey, J. S.; Seth, J.; Palaniappan, V.; Bocain, D. F. J. Am. Chem. Soc. 1996, 118, 3996. (j) Sailor, M. J.; Curtis, C. L. Adv. Mater. 1994, 6, 688. (k) Brigelletti, F.; Flamigni, L.; Balzani, V.; Collin, J.; Sauvage, J.; Sour, A.; Constable, E. C.; Thompson, A. M. W. C. J. Am. Chem. Soc. 1994, 116, 7692. Wu, C.; Bein, T. Science 1994, 264, 1757. Moeroer, W. E. Science 1994, 265, 46. (n) Sessler J. L.; Capuano, V. L.; Harriman, A. J. Am. Chem. Soc. 1993, 115, 4618. (o) Farazdel, A.; Dupuis, M.; Clementi, E.; Aviram. A. J. Am. Chem. Soc. 1990, 112, 4206. (p) Tour, J. M.; Wu, R.; Schumm, J. S. J. Am. Chem. Soc. 1991, 113, 7064. (q) Dai, H.; Wong, E. W.; Lieber, C. M. Science 1996, 272, 523. (r) Wu, R.; Schumm, J. S.; Pearson, D. L.; Tour, J. M. J. Org. Chem. 1996, 61, 6906. (s) Ward, M. D. Chem. Ind. 1996, 569.
13. For some recent background work on the formation of molecular-based transporters and devices, see: (a) Grosshenny, V.; Harriman, A.; Ziessel R. Angew. Chem., Int. Ed. Engl. 1995, 34, 1100. (b) Langler, L.; Stockman, L.; Heremans, J. P.; Bayor, V.; Oik, C. H.; Van Haesendonck, C.; Bruynseraede, Y.; Issi, J.-P. Synth. Met. 1995, 70, 1393. Pascual, J. I.; Méndez, J.; Gómez-Herrero, J.; Baró, A. M.; Garcia, N.; Landman, U.; Luedtker, W. D.; Bogachek, E. N.; Cheng, H.-P. Science 1995, 267, 1793. Purcell, S. T.; Garcia, N.; Binh, V. T.; Jones, L., II; Tour, J. M. J. Am. Chem. Soc. 1994, 116, 11985. (e) Martin, C. R. Science 1994, 266, 1961. (f) Seth, J.; Palaniappan, V.; Johnson, T. E.; Prathapan, S.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1994, 116, 10578. (g) Gust, D. Nature 1994, 372, 133. (h) Wu, C.; Bein, T. Science 1994, 266, 1013. Wagner, R. W.; Lindsey, J. S.; Seth, J.; Palaniappan, V.; Bocain, D. F. J. Am. Chem. Soc. 1996, 118, 3996. (j) Sailor, M. J.; Curtis, C. L. Adv. Mater. 1994, 6, 688. (k) Brigelletti, F.; Flamigni, L.; Balzani, V.; Collin, J.; Sauvage, J.; Sour, A.; Constable, E. C.; Thompson, A. M. W. C. J. Am. Chem. Soc. 1994, 116, 7692. Wu, C.; Bein, T. Science 1994, 264, 1757. Moeroer, W. E. Science 1994, 265, 46. (n) Sessler J. L.; Capuano, V. L.; Harriman, A. J. Am. Chem. Soc. 1993, 115, 4618. (o) Farazdel, A.; Dupuis, M.; Clementi, E.; Aviram. A. J. Am. Chem. Soc. 1990, 112, 4206. (p) Tour, J. M.; Wu, R.; Schumm, J. S. J. Am. Chem. Soc. 1991, 113, 7064. (q) Dai, H.; Wong, E. W.; Lieber, C. M. Science 1996, 272, 523. (r) Wu, R.; Schumm, J. S.; Pearson, D. L.; Tour, J. M. J. Org. Chem. 1996, 61, 6906. (s) Ward, M. D. Chem. Ind. 1996, 569.
14. For some recent background work on the formation of molecular-based transporters and devices, see: (a) Grosshenny, V.; Harriman, A.; Ziessel R. Angew. Chem., Int. Ed. Engl. 1995, 34, 1100. (b) Langler, L.; Stockman, L.; Heremans, J. P.; Bayor, V.; Oik, C. H.; Van Haesendonck, C.; Bruynseraede, Y.; Issi, J.-P. Synth. Met. 1995, 70, 1393. Pascual, J. I.; Méndez, J.; Gómez-Herrero, J.; Baró, A. M.; Garcia, N.; Landman, U.; Luedtker, W. D.; Bogachek, E. N.; Cheng, H.-P. Science 1995, 267, 1793. Purcell, S. T.; Garcia, N.; Binh, V. T.; Jones, L., II; Tour, J. M. J. Am. Chem. Soc. 1994, 116, 11985. (e) Martin, C. R. Science 1994, 266, 1961. (f) Seth, J.; Palaniappan, V.; Johnson, T. E.; Prathapan, S.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1994, 116, 10578. (g) Gust, D. Nature 1994, 372, 133. (h) Wu, C.; Bein, T. Science 1994, 266, 1013. Wagner, R. W.; Lindsey, J. S.; Seth, J.; Palaniappan, V.; Bocain, D. F. J. Am. Chem. Soc. 1996, 118, 3996. (j) Sailor, M. J.; Curtis, C. L. Adv. Mater. 1994, 6, 688. (k) Brigelletti, F.; Flamigni, L.; Balzani, V.; Collin, J.; Sauvage, J.; Sour, A.; Constable, E. C.; Thompson, A. M. W. C. J. Am. Chem. Soc. 1994, 116, 7692. Wu, C.; Bein, T. Science 1994, 264, 1757. Moeroer, W. E. Science 1994, 265, 46. (n) Sessler J. L.; Capuano, V. L.; Harriman, A. J. Am. Chem. Soc. 1993, 115, 4618. (o) Farazdel, A.; Dupuis, M.; Clementi, E.; Aviram. A. J. Am. Chem. Soc. 1990, 112, 4206. (p) Tour, J. M.; Wu, R.; Schumm, J. S. J. Am. Chem. Soc. 1991, 113, 7064. (q) Dai, H.; Wong, E. W.; Lieber, C. M. Science 1996, 272, 523. (r) Wu, R.; Schumm, J. S.; Pearson, D. L.; Tour, J. M. J. Org. Chem. 1996, 61, 6906. (s) Ward, M. D. Chem. Ind. 1996, 569.
15. For some recent background work on the formation of molecular-based transporters and devices, see: (a) Grosshenny, V.; Harriman, A.; Ziessel R. Angew. Chem., Int. Ed. Engl. 1995, 34, 1100. (b) Langler, L.; Stockman, L.; Heremans, J. P.; Bayor, V.; Oik, C. H.; Van Haesendonck, C.; Bruynseraede, Y.; Issi, J.-P. Synth. Met. 1995, 70, 1393. Pascual, J. I.; Méndez, J.; Gómez-Herrero, J.; Baró, A. M.; Garcia, N.; Landman, U.; Luedtker, W. D.; Bogachek, E. N.; Cheng, H.-P. Science 1995, 267, 1793. Purcell, S. T.; Garcia, N.; Binh, V. T.; Jones, L., II; Tour, J. M. J. Am. Chem. Soc. 1994, 116, 11985. (e) Martin, C. R. Science 1994, 266, 1961. (f) Seth, J.; Palaniappan, V.; Johnson, T. E.; Prathapan, S.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1994, 116, 10578. (g) Gust, D. Nature 1994, 372, 133. (h) Wu, C.; Bein, T. Science 1994, 266, 1013. Wagner, R. W.; Lindsey, J. S.; Seth, J.; Palaniappan, V.; Bocain, D. F. J. Am. Chem. Soc. 1996, 118, 3996. (j) Sailor, M. J.; Curtis, C. L. Adv. Mater. 1994, 6, 688. (k) Brigelletti, F.; Flamigni, L.; Balzani, V.; Collin, J.; Sauvage, J.; Sour, A.; Constable, E. C.; Thompson, A. M. W. C. J. Am. Chem. Soc. 1994, 116, 7692. Wu, C.; Bein, T. Science 1994, 264, 1757. Moeroer, W. E. Science 1994, 265, 46. (n) Sessler J. L.; Capuano, V. L.; Harriman, A. J. Am. Chem. Soc. 1993, 115, 4618. (o) Farazdel, A.; Dupuis, M.; Clementi, E.; Aviram. A. J. Am. Chem. Soc. 1990, 112, 4206. (p) Tour, J. M.; Wu, R.; Schumm, J. S. J. Am. Chem. Soc. 1991, 113, 7064. (q) Dai, H.; Wong, E. W.; Lieber, C. M. Science 1996, 272, 523. (r) Wu, R.; Schumm, J. S.; Pearson, D. L.; Tour, J. M. J. Org. Chem. 1996, 61, 6906. (s) Ward, M. D. Chem. Ind. 1996, 569.
16. For some recent background work on the formation of molecular-based transporters and devices, see: (a) Grosshenny, V.; Harriman, A.; Ziessel R. Angew. Chem., Int. Ed. Engl. 1995, 34, 1100. (b) Langler, L.; Stockman, L.; Heremans, J. P.; Bayor, V.; Oik, C. H.; Van Haesendonck, C.; Bruynseraede, Y.; Issi, J.-P. Synth. Met. 1995, 70, 1393. Pascual, J. I.; Méndez, J.; Gómez-Herrero, J.; Baró, A. M.; Garcia, N.; Landman, U.; Luedtker, W. D.; Bogachek, E. N.; Cheng, H.-P. Science 1995, 267, 1793. Purcell, S. T.; Garcia, N.; Binh, V. T.; Jones, L., II; Tour, J. M. J. Am. Chem. Soc. 1994, 116, 11985. (e) Martin, C. R. Science 1994, 266, 1961. (f) Seth, J.; Palaniappan, V.; Johnson, T. E.; Prathapan, S.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1994, 116, 10578. (g) Gust, D. Nature 1994, 372, 133. (h) Wu, C.; Bein, T. Science 1994, 266, 1013. Wagner, R. W.; Lindsey, J. S.; Seth, J.; Palaniappan, V.; Bocain, D. F. J. Am. Chem. Soc. 1996, 118, 3996. (j) Sailor, M. J.; Curtis, C. L. Adv. Mater. 1994, 6, 688. (k) Brigelletti, F.; Flamigni, L.; Balzani, V.; Collin, J.; Sauvage, J.; Sour, A.; Constable, E. C.; Thompson, A. M. W. C. J. Am. Chem. Soc. 1994, 116, 7692. Wu, C.; Bein, T. Science 1994, 264, 1757. Moeroer, W. E. Science 1994, 265, 46. (n) Sessler J. L.; Capuano, V. L.; Harriman, A. J. Am. Chem. Soc. 1993, 115, 4618. (o) Farazdel, A.; Dupuis, M.; Clementi, E.; Aviram. A. J. Am. Chem. Soc. 1990, 112, 4206. (p) Tour, J. M.; Wu, R.; Schumm, J. S. J. Am. Chem. Soc. 1991, 113, 7064. (q) Dai, H.; Wong, E. W.; Lieber, C. M. Science 1996, 272, 523. (r) Wu, R.; Schumm, J. S.; Pearson, D. L.; Tour, J. M. J. Org. Chem. 1996, 61, 6906. (s) Ward, M. D. Chem. Ind. 1996, 569.
17. For some recent background work on the formation of molecular-based transporters and devices, see: (a) Grosshenny, V.; Harriman, A.; Ziessel R. Angew. Chem., Int. Ed. Engl. 1995, 34, 1100. (b) Langler, L.; Stockman, L.; Heremans, J. P.; Bayor, V.; Oik, C. H.; Van Haesendonck, C.; Bruynseraede, Y.; Issi, J.-P. Synth. Met. 1995, 70, 1393. Pascual, J. I.; Méndez, J.; Gómez-Herrero, J.; Baró, A. M.; Garcia, N.; Landman, U.; Luedtker, W. D.; Bogachek, E. N.; Cheng, H.-P. Science 1995, 267, 1793. Purcell, S. T.; Garcia, N.; Binh, V. T.; Jones, L., II; Tour, J. M. J. Am. Chem. Soc. 1994, 116, 11985. (e) Martin, C. R. Science 1994, 266, 1961. (f) Seth, J.; Palaniappan, V.; Johnson, T. E.; Prathapan, S.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1994, 116, 10578. (g) Gust, D. Nature 1994, 372, 133. (h) Wu, C.; Bein, T. Science 1994, 266, 1013. Wagner, R. W.; Lindsey, J. S.; Seth, J.; Palaniappan, V.; Bocain, D. F. J. Am. Chem. Soc. 1996, 118, 3996. (j) Sailor, M. J.; Curtis, C. L. Adv. Mater. 1994, 6, 688. (k) Brigelletti, F.; Flamigni, L.; Balzani, V.; Collin, J.; Sauvage, J.; Sour, A.; Constable, E. C.; Thompson, A. M. W. C. J. Am. Chem. Soc. 1994, 116, 7692. Wu, C.; Bein, T. Science 1994, 264, 1757. Moeroer, W. E. Science 1994, 265, 46. (n) Sessler J. L.; Capuano, V. L.; Harriman, A. J. Am. Chem. Soc. 1993, 115, 4618. (o) Farazdel, A.; Dupuis, M.; Clementi, E.; Aviram. A. J. Am. Chem. Soc. 1990, 112, 4206. (p) Tour, J. M.; Wu, R.; Schumm, J. S. J. Am. Chem. Soc. 1991, 113, 7064. (q) Dai, H.; Wong, E. W.; Lieber, C. M. Science 1996, 272, 523. (r) Wu, R.; Schumm, J. S.; Pearson, D. L.; Tour, J. M. J. Org. Chem. 1996, 61, 6906. (s) Ward, M. D. Chem. Ind. 1996, 569.
18. For some recent background work on the formation of molecular-based transporters and devices, see: (a) Grosshenny, V.; Harriman, A.; Ziessel R. Angew. Chem., Int. Ed. Engl. 1995, 34, 1100. (b) Langler, L.; Stockman, L.; Heremans, J. P.; Bayor, V.; Oik, C. H.; Van Haesendonck, C.; Bruynseraede, Y.; Issi, J.-P. Synth. Met. 1995, 70, 1393. Pascual, J. I.; Méndez, J.; Gómez-Herrero, J.; Baró, A. M.; Garcia, N.; Landman, U.; Luedtker, W. D.; Bogachek, E. N.; Cheng, H.-P. Science 1995, 267, 1793. Purcell, S. T.; Garcia, N.; Binh, V. T.; Jones, L., II; Tour, J. M. J. Am. Chem. Soc. 1994, 116, 11985. (e) Martin, C. R. Science 1994, 266, 1961. (f) Seth, J.; Palaniappan, V.; Johnson, T. E.; Prathapan, S.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1994, 116, 10578. (g) Gust, D. Nature 1994, 372, 133. (h) Wu, C.; Bein, T. Science 1994, 266, 1013. Wagner, R. W.; Lindsey, J. S.; Seth, J.; Palaniappan, V.; Bocain, D. F. J. Am. Chem. Soc. 1996, 118, 3996. (j) Sailor, M. J.; Curtis, C. L. Adv. Mater. 1994, 6, 688. (k) Brigelletti, F.; Flamigni, L.; Balzani, V.; Collin, J.; Sauvage, J.; Sour, A.; Constable, E. C.; Thompson, A. M. W. C. J. Am. Chem. Soc. 1994, 116, 7692. Wu, C.; Bein, T. Science 1994, 264, 1757. Moeroer, W. E. Science 1994, 265, 46. (n) Sessler J. L.; Capuano, V. L.; Harriman, A. J. Am. Chem. Soc. 1993, 115, 4618. (o) Farazdel, A.; Dupuis, M.; Clementi, E.; Aviram. A. J. Am. Chem. Soc. 1990, 112, 4206. (p) Tour, J. M.; Wu, R.; Schumm, J. S. J. Am. Chem. Soc. 1991, 113, 7064. (q) Dai, H.; Wong, E. W.; Lieber, C. M. Science 1996, 272, 523. (r) Wu, R.; Schumm, J. S.; Pearson, D. L.; Tour, J. M. J. Org. Chem. 1996, 61, 6906. (s) Ward, M. D. Chem. Ind. 1996, 569.
19. For some recent background work on the formation of molecular-based transporters and devices, see: (a) Grosshenny, V.; Harriman, A.; Ziessel R. Angew. Chem., Int. Ed. Engl. 1995, 34, 1100. (b) Langler, L.; Stockman, L.; Heremans, J. P.; Bayor, V.; Oik, C. H.; Van Haesendonck, C.; Bruynseraede, Y.; Issi, J.-P. Synth. Met. 1995, 70, 1393. Pascual, J. I.; Méndez, J.; Gómez-Herrero, J.; Baró, A. M.; Garcia, N.; Landman, U.; Luedtker, W. D.; Bogachek, E. N.; Cheng, H.-P. Science 1995, 267, 1793. Purcell, S. T.; Garcia, N.; Binh, V. T.; Jones, L., II; Tour, J. M. J. Am. Chem. Soc. 1994, 116, 11985. (e) Martin, C. R. Science 1994, 266, 1961. (f) Seth, J.; Palaniappan, V.; Johnson, T. E.; Prathapan, S.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1994, 116, 10578. (g) Gust, D. Nature 1994, 372, 133. (h) Wu, C.; Bein, T. Science 1994, 266, 1013. Wagner, R. W.; Lindsey, J. S.; Seth, J.; Palaniappan, V.; Bocain, D. F. J. Am. Chem. Soc. 1996, 118, 3996. (j) Sailor, M. J.; Curtis, C. L. Adv. Mater. 1994, 6, 688. (k) Brigelletti, F.; Flamigni, L.; Balzani, V.; Collin, J.; Sauvage, J.; Sour, A.; Constable, E. C.; Thompson, A. M. W. C. J. Am. Chem. Soc. 1994, 116, 7692. Wu, C.; Bein, T. Science 1994, 264, 1757. Moeroer, W. E. Science 1994, 265, 46. (n) Sessler J. L.; Capuano, V. L.; Harriman, A. J. Am. Chem. Soc. 1993, 115, 4618. (o) Farazdel, A.; Dupuis, M.; Clementi, E.; Aviram. A. J. Am. Chem. Soc. 1990, 112, 4206. (p) Tour, J. M.; Wu, R.; Schumm, J. S. J. Am. Chem. Soc. 1991, 113, 7064. (q) Dai, H.; Wong, E. W.; Lieber, C. M. Science 1996, 272, 523. (r) Wu, R.; Schumm, J. S.; Pearson, D. L.; Tour, J. M. J. Org. Chem. 1996, 61, 6906. (s) Ward, M. D. Chem. Ind. 1996, 569.
20. For some recent background work on the formation of molecular-based transporters and devices, see: (a) Grosshenny, V.; Harriman, A.; Ziessel R. Angew. Chem., Int. Ed. Engl. 1995, 34, 1100. (b) Langler, L.; Stockman, L.; Heremans, J. P.; Bayor, V.; Oik, C. H.; Van Haesendonck, C.; Bruynseraede, Y.; Issi, J.-P. Synth. Met. 1995, 70, 1393. Pascual, J. I.; Méndez, J.; Gómez-Herrero, J.; Baró, A. M.; Garcia, N.; Landman, U.; Luedtker, W. D.; Bogachek, E. N.; Cheng, H.-P. Science 1995, 267, 1793. Purcell, S. T.; Garcia, N.; Binh, V. T.; Jones, L., II; Tour, J. M. J. Am. Chem. Soc. 1994, 116, 11985. (e) Martin, C. R. Science 1994, 266, 1961. (f) Seth, J.; Palaniappan, V.; Johnson, T. E.; Prathapan, S.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1994, 116, 10578. (g) Gust, D. Nature 1994, 372, 133. (h) Wu, C.; Bein, T. Science 1994, 266, 1013. Wagner, R. W.; Lindsey, J. S.; Seth, J.; Palaniappan, V.; Bocain, D. F. J. Am. Chem. Soc. 1996, 118, 3996. (j) Sailor, M. J.; Curtis, C. L. Adv. Mater. 1994, 6, 688. (k) Brigelletti, F.; Flamigni, L.; Balzani, V.; Collin, J.; Sauvage, J.; Sour, A.; Constable, E. C.; Thompson, A. M. W. C. J. Am. Chem. Soc. 1994, 116, 7692. Wu, C.; Bein, T. Science 1994, 264, 1757. Moeroer, W. E. Science 1994, 265, 46. (n) Sessler J. L.; Capuano, V. L.; Harriman, A. J. Am. Chem. Soc. 1993, 115, 4618. (o) Farazdel, A.; Dupuis, M.; Clementi, E.; Aviram. A. J. Am. Chem. Soc. 1990, 112, 4206. (p) Tour, J. M.; Wu, R.; Schumm, J. S. J. Am. Chem. Soc. 1991, 113, 7064. (q) Dai, H.; Wong, E. W.; Lieber, C. M. Science 1996, 272, 523. (r) Wu, R.; Schumm, J. S.; Pearson, D. L.; Tour, J. M. J. Org. Chem. 1996, 61, 6906. (s) Ward, M. D. Chem. Ind. 1996, 569.
21. For some recent background work on the formation of molecular-based transporters and devices, see: (a) Grosshenny, V.; Harriman, A.; Ziessel R. Angew. Chem., Int. Ed. Engl. 1995, 34, 1100. (b) Langler, L.; Stockman, L.; Heremans, J. P.; Bayor, V.; Oik, C. H.; Van Haesendonck, C.; Bruynseraede, Y.; Issi, J.-P. Synth. Met. 1995, 70, 1393. Pascual, J. I.; Méndez, J.; Gómez-Herrero, J.; Baró, A. M.; Garcia, N.; Landman, U.; Luedtker, W. D.; Bogachek, E. N.; Cheng, H.-P. Science 1995, 267, 1793. Purcell, S. T.; Garcia, N.; Binh, V. T.; Jones, L., II; Tour, J. M. J. Am. Chem. Soc. 1994, 116, 11985. (e) Martin, C. R. Science 1994, 266, 1961. (f) Seth, J.; Palaniappan, V.; Johnson, T. E.; Prathapan, S.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1994, 116, 10578. (g) Gust, D. Nature 1994, 372, 133. (h) Wu, C.; Bein, T. Science 1994, 266, 1013. Wagner, R. W.; Lindsey, J. S.; Seth, J.; Palaniappan, V.; Bocain, D. F. J. Am. Chem. Soc. 1996, 118, 3996. (j) Sailor, M. J.; Curtis, C. L. Adv. Mater. 1994, 6, 688. (k) Brigelletti, F.; Flamigni, L.; Balzani, V.; Collin, J.; Sauvage, J.; Sour, A.; Constable, E. C.; Thompson, A. M. W. C. J. Am. Chem. Soc. 1994, 116, 7692. Wu, C.; Bein, T. Science 1994, 264, 1757. Moeroer, W. E. Science 1994, 265, 46. (n) Sessler J. L.; Capuano, V. L.; Harriman, A. J. Am. Chem. Soc. 1993, 115, 4618. (o) Farazdel, A.; Dupuis, M.; Clementi, E.; Aviram. A. J. Am. Chem. Soc. 1990, 112, 4206. (p) Tour, J. M.; Wu, R.; Schumm, J. S. J. Am. Chem. Soc. 1991, 113, 7064. (q) Dai, H.; Wong, E. W.; Lieber, C. M. Science 1996, 272, 523. (r) Wu, R.; Schumm, J. S.; Pearson, D. L.; Tour, J. M. J. Org. Chem. 1996, 61, 6906. (s) Ward, M. D. Chem. Ind. 1996, 569.
22. For some recent background work on the formation of molecular-based transporters and devices, see: (a) Grosshenny, V.; Harriman, A.; Ziessel R. Angew. Chem., Int. Ed. Engl. 1995, 34, 1100. (b) Langler, L.; Stockman, L.; Heremans, J. P.; Bayor, V.; Oik, C. H.; Van Haesendonck, C.; Bruynseraede, Y.; Issi, J.-P. Synth. Met. 1995, 70, 1393. Pascual, J. I.; Méndez, J.; Gómez-Herrero, J.; Baró, A. M.; Garcia, N.; Landman, U.; Luedtker, W. D.; Bogachek, E. N.; Cheng, H.-P. Science 1995, 267, 1793. Purcell, S. T.; Garcia, N.; Binh, V. T.; Jones, L., II; Tour, J. M. J. Am. Chem. Soc. 1994, 116, 11985. (e) Martin, C. R. Science 1994, 266, 1961. (f) Seth, J.; Palaniappan, V.; Johnson, T. E.; Prathapan, S.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1994, 116, 10578. (g) Gust, D. Nature 1994, 372, 133. (h) Wu, C.; Bein, T. Science 1994, 266, 1013. Wagner, R. W.; Lindsey, J. S.; Seth, J.; Palaniappan, V.; Bocain, D. F. J. Am. Chem. Soc. 1996, 118, 3996. (j) Sailor, M. J.; Curtis, C. L. Adv. Mater. 1994, 6, 688. (k) Brigelletti, F.; Flamigni, L.; Balzani, V.; Collin, J.; Sauvage, J.; Sour, A.; Constable, E. C.; Thompson, A. M. W. C. J. Am. Chem. Soc. 1994, 116, 7692. Wu, C.; Bein, T. Science 1994, 264, 1757. Moeroer, W. E. Science 1994, 265, 46. (n) Sessler J. L.; Capuano, V. L.; Harriman, A. J. Am. Chem. Soc. 1993, 115, 4618. (o) Farazdel, A.; Dupuis, M.; Clementi, E.; Aviram. A. J. Am. Chem. Soc. 1990, 112, 4206. (p) Tour, J. M.; Wu, R.; Schumm, J. S. J. Am. Chem. Soc. 1991, 113, 7064. (q) Dai, H.; Wong, E. W.; Lieber, C. M. Science 1996, 272, 523. (r) Wu, R.; Schumm, J. S.; Pearson, D. L.; Tour, J. M. J. Org. Chem. 1996, 61, 6906. (s) Ward, M. D. Chem. Ind. 1996, 569.
23. For some recent background work on the formation of molecular-based transporters and devices, see: (a) Grosshenny, V.; Harriman, A.; Ziessel R. Angew. Chem., Int. Ed. Engl. 1995, 34, 1100. (b) Langler, L.; Stockman, L.; Heremans, J. P.; Bayor, V.; Oik, C. H.; Van Haesendonck, C.; Bruynseraede, Y.; Issi, J.-P. Synth. Met. 1995, 70, 1393. Pascual, J. I.; Méndez, J.; Gómez-Herrero, J.; Baró, A. M.; Garcia, N.; Landman, U.; Luedtker, W. D.; Bogachek, E. N.; Cheng, H.-P. Science 1995, 267, 1793. Purcell, S. T.; Garcia, N.; Binh, V. T.; Jones, L., II; Tour, J. M. J. Am. Chem. Soc. 1994, 116, 11985. (e) Martin, C. R. Science 1994, 266, 1961. (f) Seth, J.; Palaniappan, V.; Johnson, T. E.; Prathapan, S.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1994, 116, 10578. (g) Gust, D. Nature 1994, 372, 133. (h) Wu, C.; Bein, T. Science 1994, 266, 1013. Wagner, R. W.; Lindsey, J. S.; Seth, J.; Palaniappan, V.; Bocain, D. F. J. Am. Chem. Soc. 1996, 118, 3996. (j) Sailor, M. J.; Curtis, C. L. Adv. Mater. 1994, 6, 688. (k) Brigelletti, F.; Flamigni, L.; Balzani, V.; Collin, J.; Sauvage, J.; Sour, A.; Constable, E. C.; Thompson, A. M. W. C. J. Am. Chem. Soc. 1994, 116, 7692. Wu, C.; Bein, T. Science 1994, 264, 1757. Moeroer, W. E. Science 1994, 265, 46. (n) Sessler J. L.; Capuano, V. L.; Harriman, A. J. Am. Chem. Soc. 1993, 115, 4618. (o) Farazdel, A.; Dupuis, M.; Clementi, E.; Aviram. A. J. Am. Chem. Soc. 1990, 112, 4206. (p) Tour, J. M.; Wu, R.; Schumm, J. S. J. Am. Chem. Soc. 1991, 113, 7064. (q) Dai, H.; Wong, E. W.; Lieber, C. M. Science 1996, 272, 523. (r) Wu, R.; Schumm, J. S.; Pearson, D. L.; Tour, J. M. J. Org. Chem. 1996, 61, 6906. (s) Ward, M. D. Chem. Ind. 1996, 569.
24. For some recent background work on the formation of molecular-based transporters and devices, see: (a) Grosshenny, V.; Harriman, A.; Ziessel R. Angew. Chem., Int. Ed. Engl. 1995, 34, 1100. (b) Langler, L.; Stockman, L.; Heremans, J. P.; Bayor, V.; Oik, C. H.; Van Haesendonck, C.; Bruynseraede, Y.; Issi, J.-P. Synth. Met. 1995, 70, 1393. Pascual, J. I.; Méndez, J.; Gómez-Herrero, J.; Baró, A. M.; Garcia, N.; Landman, U.; Luedtker, W. D.; Bogachek, E. N.; Cheng, H.-P. Science 1995, 267, 1793. Purcell, S. T.; Garcia, N.; Binh, V. T.; Jones, L., II; Tour, J. M. J. Am. Chem. Soc. 1994, 116, 11985. (e) Martin, C. R. Science 1994, 266, 1961. (f) Seth, J.; Palaniappan, V.; Johnson, T. E.; Prathapan, S.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1994, 116, 10578. (g) Gust, D. Nature 1994, 372, 133. (h) Wu, C.; Bein, T. Science 1994, 266, 1013. Wagner, R. W.; Lindsey, J. S.; Seth, J.; Palaniappan, V.; Bocain, D. F. J. Am. Chem. Soc. 1996, 118, 3996. (j) Sailor, M. J.; Curtis, C. L. Adv. Mater. 1994, 6, 688. (k) Brigelletti, F.; Flamigni, L.; Balzani, V.; Collin, J.; Sauvage, J.; Sour, A.; Constable, E. C.; Thompson, A. M. W. C. J. Am. Chem. Soc. 1994, 116, 7692. Wu, C.; Bein, T. Science 1994, 264, 1757. Moeroer, W. E. Science 1994, 265, 46. (n) Sessler J. L.; Capuano, V. L.; Harriman, A. J. Am. Chem. Soc. 1993, 115, 4618. (o) Farazdel, A.; Dupuis, M.; Clementi, E.; Aviram. A. J. Am. Chem. Soc. 1990, 112, 4206. (p) Tour, J. M.; Wu, R.; Schumm, J. S. J. Am. Chem. Soc. 1991, 113, 7064. (q) Dai, H.; Wong, E. W.; Lieber, C. M. Science 1996, 272, 523. (r) Wu, R.; Schumm, J. S.; Pearson, D. L.; Tour, J. M. J. Org. Chem. 1996, 61, 6906. (s) Ward, M. D. Chem. Ind. 1996, 569.
25. For some recent background work on the formation of molecular-based transporters and devices, see: (a) Grosshenny, V.; Harriman, A.; Ziessel R. Angew. Chem., Int. Ed. Engl. 1995, 34, 1100. (b) Langler, L.; Stockman, L.; Heremans, J. P.; Bayor, V.; Oik, C. H.; Van Haesendonck, C.; Bruynseraede, Y.; Issi, J.-P. Synth. Met. 1995, 70, 1393. Pascual, J. I.; Méndez, J.; Gómez-Herrero, J.; Baró, A. M.; Garcia, N.; Landman, U.; Luedtker, W. D.; Bogachek, E. N.; Cheng, H.-P. Science 1995, 267, 1793. Purcell, S. T.; Garcia, N.; Binh, V. T.; Jones, L., II; Tour, J. M. J. Am. Chem. Soc. 1994, 116, 11985. (e) Martin, C. R. Science 1994, 266, 1961. (f) Seth, J.; Palaniappan, V.; Johnson, T. E.; Prathapan, S.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1994, 116, 10578. (g) Gust, D. Nature 1994, 372, 133. (h) Wu, C.; Bein, T. Science 1994, 266, 1013. Wagner, R. W.; Lindsey, J. S.; Seth, J.; Palaniappan, V.; Bocain, D. F. J. Am. Chem. Soc. 1996, 118, 3996. (j) Sailor, M. J.; Curtis, C. L. Adv. Mater. 1994, 6, 688. (k) Brigelletti, F.; Flamigni, L.; Balzani, V.; Collin, J.; Sauvage, J.; Sour, A.; Constable, E. C.; Thompson, A. M. W. C. J. Am. Chem. Soc. 1994, 116, 7692. Wu, C.; Bein, T. Science 1994, 264, 1757. Moeroer, W. E. Science 1994, 265, 46. (n) Sessler J. L.; Capuano, V. L.; Harriman, A. J. Am. Chem. Soc. 1993, 115, 4618. (o) Farazdel, A.; Dupuis, M.; Clementi, E.; Aviram. A. J. Am. Chem. Soc. 1990, 112, 4206. (p) Tour, J. M.; Wu, R.; Schumm, J. S. J. Am. Chem. Soc. 1991, 113, 7064. (q) Dai, H.; Wong, E. W.; Lieber, C. M. Science 1996, 272, 523. (r) Wu, R.; Schumm, J. S.; Pearson, D. L.; Tour, J. M. J. Org. Chem. 1996, 61, 6906. (s) Ward, M. D. Chem. Ind. 1996, 569.
26. For some recent background work on the formation of molecular-based transporters and devices, see: (a) Grosshenny, V.; Harriman, A.; Ziessel R. Angew. Chem., Int. Ed. Engl. 1995, 34, 1100. (b) Langler, L.; Stockman, L.; Heremans, J. P.; Bayor, V.; Oik, C. H.; Van Haesendonck, C.; Bruynseraede, Y.; Issi, J.-P. Synth. Met. 1995, 70, 1393. Pascual, J. I.; Méndez, J.; Gómez-Herrero, J.; Baró, A. M.; Garcia, N.; Landman, U.; Luedtker, W. D.; Bogachek, E. N.; Cheng, H.-P. Science 1995, 267, 1793. Purcell, S. T.; Garcia, N.; Binh, V. T.; Jones, L., II; Tour, J. M. J. Am. Chem. Soc. 1994, 116, 11985. (e) Martin, C. R. Science 1994, 266, 1961. (f) Seth, J.; Palaniappan, V.; Johnson, T. E.; Prathapan, S.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1994, 116, 10578. (g) Gust, D. Nature 1994, 372, 133. (h) Wu, C.; Bein, T. Science 1994, 266, 1013. Wagner, R. W.; Lindsey, J. S.; Seth, J.; Palaniappan, V.; Bocain, D. F. J. Am. Chem. Soc. 1996, 118, 3996. (j) Sailor, M. J.; Curtis, C. L. Adv. Mater. 1994, 6, 688. (k) Brigelletti, F.; Flamigni, L.; Balzani, V.; Collin, J.; Sauvage, J.; Sour, A.; Constable, E. C.; Thompson, A. M. W. C. J. Am. Chem. Soc. 1994, 116, 7692. Wu, C.; Bein, T. Science 1994, 264, 1757. Moeroer, W. E. Science 1994, 265, 46. (n) Sessler J. L.; Capuano, V. L.; Harriman, A. J. Am. Chem. Soc. 1993, 115, 4618. (o) Farazdel, A.; Dupuis, M.; Clementi, E.; Aviram. A. J. Am. Chem. Soc. 1990, 112, 4206. (p) Tour, J. M.; Wu, R.; Schumm, J. S. J. Am. Chem. Soc. 1991, 113, 7064. (q) Dai, H.; Wong, E. W.; Lieber, C. M. Science 1996, 272, 523. (r) Wu, R.; Schumm, J. S.; Pearson, D. L.; Tour, J. M. J. Org. Chem. 1996, 61, 6906. (s) Ward, M. D. Chem. Ind. 1996, 569.
27. "Molecular electronics" is a poorly defined term since some authors refer to it as any molecular-based system such as a film or a liquid crystalline array. Other authors, including us, have preferred to reserve the term "molecular electronics" for single molecule tasks. such as single molecule-based devices or single molecular wires. Due to this confusion, we have chosen here to follow the Petty et al. (Introduction to Molecular Electronics, Petty, M. C., Bryce, M. R., Bloor, D., Eds.; Oxford Univ. Press: New York, 1995) terminology by using two subcategories, namely "molecular materials for electronics" for bulk applications and "molecular scale electronics" for single moleculs applications.
28. Handbook of Conducting Polymers; Skotheim, T. A., Ed.; Dekker: New York, 1986.
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