Cyclodextrin-threaded conjugated polyrotaxanes as insulated molecular wires with reduced interstrand interactions

Nature Materials

Volumn 1, Issue 3, 2002, Pages 160-164

  Cacialli, Franco ^a,b   Wilson, Joanne S ^b   Michels, Jasper J ^c   Daniel, Clement ^b   Silva, Carlos ^b   Friend, Richard H ^b   Severin, Nikolai ^d   Samori, Paolo ^d,e   Rabe, Jürgen P ^d   O'connell, Michael J ^c   Taylor, Peter N ^c   Anderson, Harry L ^c  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

^b UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^c UNIVERSITY OF OXFORD   (United Kingdom)

^d HUMBOLDT UNIVERSITY   (Germany)

^e Istituto Per La Sintesi Organica E La Fotoreattività   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CATHODES; LIGHT EMITTING DIODES; PHOTOLUMINESCENCE; POLYMERS;

MOLECULAR WIRES;

SUPRAMOLECULAR CHEMISTRY;

CYCLODEXTRIN; POLYMER; ROTAXANE;

ARTICLE; ATOMIC FORCE MICROSCOPY; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; CONFORMATION; ELECTRIC CONDUCTIVITY; EVALUATION; INSTRUMENTATION; LIGHT; LUMINESCENCE; MACROMOLECULE; MATERIALS TESTING; METHODOLOGY; NANOTECHNOLOGY; OPTICS; PHOTOCHEMISTRY; QUALITY CONTROL; SEMICONDUCTOR; SENSITIVITY AND SPECIFICITY;

CYCLODEXTRINS; ELECTRIC CONDUCTIVITY; LIGHT; LUMINESCENT MEASUREMENTS; MACROMOLECULAR SUBSTANCES; MATERIALS TESTING; MICROSCOPY, ATOMIC FORCE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NANOTECHNOLOGY; OPTICS; PHOTOCHEMISTRY; POLYMERS; QUALITY CONTROL; ROTAXANES; SEMICONDUCTORS; SENSITIVITY AND SPECIFICITY;

EID: 0036879479     PISSN: 14761122     EISSN: None     Source Type: Journal    
DOI: 10.1038/nmat750     Document Type: Article

References (31)

1. Cornil, J., dos Santos, D. A., Crispin, X., Silbey, R. & Brédas, J. L. Influence of interchain interactions on the absorption and luminescence of conjugated oligomers and polymers: a quantum-chemical characterization. J. Am. Chem. Soc. 120, 1289-1299 (1998).
2. Cacialli, F. Organic semiconductors for the new millennium. Phil. Trans. Royal Soc. Lond. A 358, 173-192 (2000).
3. Liang, W., Shores, M. P., Bockrath, M., Long, J. R. & Park, H. Kondo resonance in a single-molecule transistor. Nature 417, 725-729 (2002).
4. Gong, C. & Gibson, H. W. in Molecular Catenanes, Rotaxanes and Knots (eds Sauvage, J.-P. & Dietrich-Buchecker, C.) 277-321 (Wiley-VCH, Weinheim, 1999).
5. Collier, C. P. at al. Molecular-based electronically switchable tunnel junction devices, J. Am. Chem. Soc. 123, 12632-12641 (2001).
6. Raymo, F. M. & Stoddart, J. F. Interlocked macromolecules. Chem. Rev. 99, 1643-1663 (1999).
7. Nepogodiev, S. A. & Stoddart, J. F. Cydodextrin-based catenanes and rotaxanes. Chem. Rev. 98, 1959-1976 (1998).
8. Zhu, S. S. & Swager, T. M. Conducting polymetallorotaxanes: Metal ion mediated enhancements in conductivity and charge localization. J. Am. Chem. Soc. 119, 12568-12577 (1997).
9. MacLachlan, M. J., Rose, A. & Swager, T. M. A rotaxane exciplex, J. Am. Chem. Soc. 123, 9180-9181 (2001).
10. Gadret, G. et al. Optical and electroemission properties of thin films of supermolecular anthracene-based rotranes. Appl. Surf. Sci. 175, 369-373 (2001).
11. Cornil, J., Heeger, A. J. & Brédas, J. L. Effects of intermolecular interactions on the lowest excited state in luminescent conjugated polymers and oligomers. Chem. Phys. Lett. 272, 463-470 (1997).
12. Burroughes, J. H. et al. Light-emitting diodes based on conjugated polymers. Nature 347, 539-541 (1990).
13. Kraft, A., Grimsdale, A. C. & Holmes, A. B. Electroluminescent conjugated polymers - seeing polymers in a new light. Angew. Chem. Int. Edn 37, 402-428 (1998).
14. Cardin, D. J. Encapsulated conducting polymers. Adv. Mater. 14, 553-563 (2002).
15. Shimomura, T., Akai, T., Abe, T. & Ito, K. Atomic force microscopy observation of insulated molecular wire formed by conducting polymer and molecular nanotube. J. Chem. Phys. 116, 1753-1756 (2002).
16. Buey, J. & Swager, T. M. Three-strand conducting ladder polymers: two-step electropolymerization of metallorotaxanes. Angew. Chem. Int. Edn 39, 608-612 (2000).
17. Lagrost, C. et al. Host-guest complexation: a convenient route to polybithiophene composites by electrosynthesis in aqueous media. synthesis and characterization of a new material containing cydodextrins. J. Mater. Chem. 9, 2351-2358 (1999).
18. Vidal, P. L. et al. Conjugated polyrotaxanes containing coordinating units: reversible copper(I) metallation-demetillation using lithium as Intermediate scaffolding. Chem. Commun. 629-630 (1998).
19. Taylor, P. N. et al. Insulated molecular wires: synthesis of conjugated polyrotaxanes by Suzuki coupling in water. Angew. Chem. Int. Edn 39, 3456-3460 (2000).
20. Balzani, V., Credi, A., Raymo, F. M. & Stoddart, J. F. Artificial molecular machines. Angew. Chem. Int. Edn 39, 3349-3391 (2000).
21. Brouwer, A. M. et al. Photoinduction of fast, reversible translational motion in a hydrogen-bonded molecular shuttle. Science 291, 2124-2128 (2001).
22. Stanier, C. A., Alderman, S. J., Claridge, T. D. W. & Anderson, H. L. Unidirectional photoinduced shuttling in a rotaxane with a symmetric stilbene dumbbell. Angew. Chem. Int. Edn 41, 1769-1772 (2002).
23. Sirringhaus, H. et al. Two-dimensional charge transport in self-organized, high-mobility conjugated polymers. Nature 401, 685-688 (1999).
24. Barta, P., Cacialli, F., Friend, R. H. & Zagorska, M. Efficient photo and electroluminescence of regioregular poly(alkylthiophene)s. J. Appl. Phys. 84, 6279-6284 (1998).
25. Gigli, G., Barbarella, G., Favaretto, L., Cacialli, F. & Cingolani, R. High-efficiency oligothiopene-based light-emitting diodes. Appl. Phys. Lett. 75, 439-441 (1999).
26. McQuade, D. T., Kim, J. & Swager, T. M. A rotaxane exciplex, J. Am. Chem. Soc. 122, 5885-5886 (2000).
27. Liu, H. et al. Synthesis and properties of crown-ether containing poly(p-phenylenevinylene). J. Mater. Chem. 11, 3063-3067 (2001).
28. Craig, M. R., Hutchings, M. G., Claridge, T. D. W. & Anderson, H. L. Rotaxane-encapsulation enhances the stability of an azo dye in solution when bound to cellulose. Angew. Chem. Int. Edn 40, 1071-1074 (2001).
29. Kim, J.S. et al. Indium-tin oxide treatments for single- and double-layer polymeric light-emitting diodes: the relation between the anode physical, chemical, and morphological properties and the device performance. J. Appl. Phys. 84, 6859-6870 (1998).
30. Samorì, P. et al. High shape persistence in single polymer chains rigidified with lateral hydrogen bonded networks. Macromolecules 35, 5290-5294 (2002).
31. Samorì, P., Francke, V., Mangel, T., Müllen, K. & Rabe, J. P. Poly-para-phenylene-ethynylene assemblies for a potential molecular nanowire: an SFM study. Opt. Mater. 9, 390-393 (1998).