Toward molecular muscles: Design and synthesis of an electrically conducting poly[cyclooctatetrathiophene]

Macromolecules

Volumn 32, Issue 18, 1999, Pages 5982-5984

  Marsella, Michael J ^a   Reid, Rodney J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTUATORS; AROMATIC POLYMERS; COMPUTATIONAL METHODS; CONFORMATIONS; ELECTROCHEMISTRY; MOLECULAR STRUCTURE; OXIDATION; SULFUR COMPOUNDS;

POLYANNULENE; POLYCYCLOOCTATETRATHIOPHENE;

CONDUCTIVE PLASTICS;

EID: 0032681954     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma990892r     Document Type: Article

References (19)

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2. Balzani, V.; Gómez-López, M.; Stoddart, J. F. Acc. Chem. Res. 1998, 31, 405-414.
3. For a previous example of photomechanical actuation based on the isomerization of stilbene units, see: Zimmerman, E. K.; Stille, J. K. Macromolecules 1985, 18, 321-327.
4. Garratt, P. J. Aromaticity; John Wiley & Sons: New York, 1986.
5. Strauss, H. L.; Katz, T. J.; Fraenkel, G. K. J. Am. Chem. Soc. 1963, 85, 2360-2364.
6. Unlike regioisomer 3, changes occurring in the S-C-C-S dihedral angle (φ, see text) of polymer 2 do not alone ensure significant single-molecule response. Other conformational issues (such as helicity) must also be addressed. Monomer 6 is designed to function as a helical directing group, and achieving optimal single-molecule EM actuation is contingent on polymer 2 existing in a helical conformation. The ability of 6 to function as a helical directing group as well as more complete conformational analysis of polymer 2 will be reported elsewhere.
7. Kauffmann, T.; Greving, B.; Kriegesmann, R.; Mitschker, A.; Woltermann, A. Chem. Ber. 1978, 111, 1330-1336.
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12. See: McCullough, R. D.; Ewbank, P. C. In Handbook of Conducting Polymers; Skotheim, T. A., Elsenbaumer, R. L., Reynolds, J. R., Eds.; Marcel Dekker: New York, 1998.
13. Gaussian 98W (Revision A.7): Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C. Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Parkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochtersji, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malik, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzolez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1998.
14. See Supporting Information.
15. It should be noted that the bending beam method would have only reported the bulk EM actuation of 2 and thus would not in itself have definitively proven a single-molecule response.
16. Pei, Q.; Inganas, O. J. Phys. Chem. 1992, 96, 10507-10514.
17. McCullough, R. D.; Lowe, R. D.; Jayaraman, M.; Anderson, D. L. J. Org. Chem. 1993, 58, 904-912.
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19. Compound 6 may function as a helical directing group. In general, cyclooctatetrathiophenes are heterocyclic analogues of tetra-o-phenylenes, which are fragments of a double helix. For a report of the synthesis of double-helical octaphenylene from tetra-o-phenylenes, see: Rajca, A.; Safronov, A.; Rajca, S.; Shoemaker, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 489-491.