Toward isolated molecular wires: A pH-responsive canopied polypyrrole

Chemistry of Materials

Volumn 17, Issue 18, 2005, Pages 4622-4629

  Lee, Dongwhan ^a,b   Swager, Timothy M ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MOLECULAR WIRES; OXIDATIVE POLYMERIZATION; PHENYL GROUPS; POLYMER CHAINS;

CHARGE CARRIERS; ELECTRIC CONDUCTIVITY; ELECTROLYTES; ELECTROPOLYMERIZATION; MONOMERS; OXIDATION; PH EFFECTS; SYNTHESIS (CHEMICAL);

POLYPYRROLES;

EID: 25444458592     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm050803r     Document Type: Article

References (57)

1. Electronic Materials: The Oligomer Approach; Müllen, K., Wegner, G., Eds.; Wiley-VCH: New York, 1998.
2. Organic Electronic Materials: Conjugated Polymers and Low Molecular Weight Organic Solids; Farchioni, R., Grosso, G., Eds.; Springer: Berlin, 2001.
3. Special Issue on Organic Electronics. Chem. Mater. 2004, 16, No. 23.
4. Swager, T. M. Acc. Chem. Res. 1998, 31, 201-207.
5. McQuade, D. T.; Pullen, A. E.; Swager, T. M. Chem. Rev. 2000, 100, 2537-2574.
6. Wosnick, J. H.; Swager, T. M. Curr. Opin. Chem. Biol. 2000, 4, 715-720.
7. Lee, D.; Swager, T. M. Synlett 2004, 149-154.
8. Holliday, B. J.; Swager, T. M. Chem. Commun. 2005, 23-36.
9. Kittlesen, G. P.; White, H. S.; Wrighton, M. S. J. Am. Chem. Soc. 1984, 106, 7389-7396.
10. Ofer, D.; Crooks, R. M.; Wrighton, M. S. J. Am. Chem. Soc. 1990, 112, 7869-7879.
11. Buey, J.; Swager, T. M. Angew. Chem., Int. Ed. 2000, 39, 608-612.
12. Cornil, J.; Beljonne, D.; Calbert, J.-P.; Brédas, J.-L. Adv. Mater. 2001, 13, 1053-1067.
13. Cacialli, F.; Wilson, J. S.; Michels, J. J.; Daniel, C.; Silva, C.; Friend, R. H.; Severin, N.; Samorí, P.; Rabe, J. P.; O'Connell, M. J.; Taylor, P. N.; Anderson, H. L. Nat. Mater. 2002, 1, 160-164.
14. Cardin, D. J. Adv. Mater. 2002, 14, 553-563.
15. van den Boogaard, M.; Bonnet, G.; van't Hof, P.; Wang, Y.; Brochon, C.; van Hutten, P.; La A.; Hadziioannou, G. Chem. Mater. 2004, 16, 4383-4385.
16. Budd, P. M.; Ghanem, B. S.; Makhseed, S.; McKeown, N. B.; Msayib, K. J.; Tattershall, C. E. Chem. Commun. 2004, 230-231.
17. Yang, J.-S.; Swager, T. M. J. Am. Chem. Soc. 1998, 120, 11864-11873.
18. Long, T. M.; Swager, T. M. J. Am. Chem. Soc. 2002, 124, 3826-3827.
19. Aspects of this work have previously been communicated: Lee, D.; Swager, T. M. J. Am. Chem. Soc. 2003, 125, 6870-6871.
20. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518-1520.
21. Novak, B. H.; Lash, T. D. J. Org. Chem. 1998, 63, 3998-4010.
22. SMART v5.05: Software for the CCD Detector System, version 5.05; Bruker AXS: Madison, WI, 1998.
23. Sheldrick, G. M. SADABS: Area-Detector Absorption Correction; University of Göttingen: Göttingen, Germany, 1996.
24. Sheldrick, G. M. SHELXTL97-2: Program for the Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.
25. Spek, A. L. PLATON, A Multipurpose Crystallographic Tool; Utrecht University: Utrecht, The Netherlands, 1998.
26. Zotti, G.; Schiavon, G. Synth. Met. 1990, 39, 183-190.
27. Kingsborough, R. P.; Swager, T. M. J. Am. Chem. Soc. 1999, 121, 8825-8834.
28. Harvey, S. C. J. Am. Chem. Soc. 1949, 71, 1121-1122.
29. Abbady, M. S.; Kandeel, M. M.; Youssef, M. S. K. Phosphorus, Sulfur, Silicon 2000, 163, 55-64.
30. Hopkins, P. B.; Fuchs, P. L. J. Org. Chem. 1978, 43, 1208-1217.
31. Barton, D. H. R.; Zard, S. Z. J. Chem. Soc., Chem. Commun. 1985, 1098-1100.
32. Barton, D. H. R.; Kervagoret, J.; Zard, S. Z. Tetrahedron 1990, 46, 7587-7598.
33. Abel, Y.; Montforts, F.-P. Tetrahedron Lett. 1997, 38, 1745-1748.
34. Abel, Y.; Haake, E.; Haake, G.; Schmidt, W.; Struve, D.; Walter, A.; Montforts, F.-P. Helv. Chim. Acta 1998, 81, 1978-1996.
35. Craig, D. J. Am. Chem. Soc. 1951, 73, 4889-4892.
36. + unless otherwise noted.
37. Kaufman, J. H.; Colaneri, N.; Scott, J. C.; Street, G. B. Phys. Rev. Lett. 1984, 53, 1005-1008.
38. Zotti, G.; Schiavon, G. Synth. Met. 1989, 30, 151-158.
39. Amemiya, T.; Hashimoto, K.; Fujishima, A. J. Electrochem. Soc. 1991, 138, 2845-2850.
40. Son, Y.; Rajeshwar, K. J. Chem. Soc., Faraday Trans. 1992, 88, 605-610.
41. As shown in Figure S3, a large hysteresis was observed in the conductivity profile of poly(7′) in oxidative and reductive potential sweeps at pH 3, indicating a significant structural reorganization upon removal and injection of electrons. Repeated potential scans resulted in a rapid decay of the conductivity of poly(7′), preventing further studies.
42. Ramondenc, Y.; Schwenninger, R.; Phan, T.; Gruber, K.; Kratky, C.; Kräutler, B. Angew. Chem., Int. Ed. Engl. 1994, 33, 889-891.
43. Schlögl, J.; Kräutler, B. Synlett 1999, 969-971.
44. Ito, S.; Murashima, T.; Ono, N. J. Chem. Soc., Perkin Trans. 1 1997, 3161-3165.
45. Ito, S.; Uno, H.; Murashima, T.; Ono, N. Chem. Commun. 1999, 2275-2276.
46. Ito, S.; Ochi, N.; Uno, H.; Murashima, T.; Ono, N. Chem. Commun. 2000, 893-894.
47. Ito, S.; Uno, H.; Murashima, T.; Ono, N. Tetrahedron Lett. 2001, 42, 45-47.
48. Ito, S.; Watanabe, H.; Uno, H.; Murashima, T.; Ono, N.; Tsai, Y. C.; Compton, R. G. Tetrahedron Lett. 2001, 42, 707-710.
49. For example, a 2-pyridyl analogue of 7 could be prepared, in which a potential metal-binding site is installed directly above the pyrrole group.
50. Chiang, J.-C.; MacDiarmid, A. G. Synth. Met. 1986, 13, 193-205.
51. MacDiarmid, A. G.; Epstein, A. J. Faraday Discuss. Chem. Soc. 1989, 88, 317-332.
52. MacDiarmid, A. G. Angew. Chem., Int. Ed. 2001, 40, 2581-2590.
53. Yu, H.-h.; Xu, B.; Swager, T. M. J. Am. Chem. Soc. 2003, 125, 1142-1143.
54. Yu, H.-h.; Pullen, A. E.; Büschel, M. G.; Swager, T. M. Angew. Chem., Int. Ed. 2004, 43, 3700-3703.
55. Inganäs, O.; Erlandsson, R.; Nylander, C.; Lundström, I. J. Phys. Chem. Solids 1984, 45, 427-432.
56. Nishizawa, M.; Matsue, T.; Uchida, I. Anal. Chem. 1992, 64, 2642-2644.
57. Talaie, A. Polymer 1997, 38, 1145-1150.