Preparation of poly(diiododiacetylene), an ordered conjugated polymer of carbon and iodine

Science

Volumn 312, Issue 5776, 2006, Pages 1030-1034

  Sun, Aiwu ^a   Lauher, Joseph W ^a   Goroff, Nancy S ^a  

^a STONY BROOK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; CARBON; CRYSTALS; HYDROGEN BONDS; IODINE; MONOMERS; POLYMERIZATION; SCAFFOLDS; SCANNING ELECTRON MICROSCOPY; SINGLE CRYSTALS; ULTRAVIOLET SPECTROSCOPY; X RAY DIFFRACTION;

ACID-BASE INTERACTIONS; IODOALKYNES; TOPOCHEMICAL POLYMERIZATION; UNADORNED CARBON CHAINS;

ORGANIC POLYMERS;

ACETYLENE DERIVATIVE; CARBON; IODINE; LEWIS ACID; NITRILE; POLY(DIIODODIACETYLENE); POLYMER; UNCLASSIFIED DRUG;

ATOMIC ABSORPTION SPECTROSCOPY; CARBON; CRYSTAL; HYDROGEN; IODINE; POLYMER; X-RAY DIFFRACTION;

ARTICLE; CHEMICAL INTERACTION; CRYSTAL STRUCTURE; HYDROGEN BOND; POLYMERIZATION; PRIORITY JOURNAL; SCANNING ELECTRON MICROSCOPY; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY; X RAY DIFFRACTION;

EID: 33646722467     PISSN: 00368075     EISSN: 10959203     Source Type: Journal    
DOI: 10.1126/science.1124621     Document Type: Article

References (40)

1. H. Shirakawa, E. J. Louis, A. G. MacDiarmid, C. K. Chiang, A. J. Heeger, J. Chem. Soc. Chem. Comm. 1977, 578 (1977).
2. R. W. Carpick, D. Y. Sasaki, M. S. Marcus, M. A. Eriksson, A. R. Burns, J. Phys. Cond. Matter 16, R679 (2004).
3. J. M. Nunzi, C. R. Phys. 3, 523 (2002).
4. C. D. Dimitrakopoulos, P. R. L. Malenfant, Adv. Mater. 14, 99 (2002).
5. D. T. McQuade, A. E. Pullen, T. M. Swager, Chem. Rev. 100, 2537 (2000).
6. J. W. Y. Lam, B. Z. Tang, Acct. Chem. Res. 38, 745 (2005).
7. G. Wegner, Z. Naturforsch. Teil B 24, 824 (1969).
8. R. H. Baughman, J. Polymer Sci. Polymer Phys. Ed. 12, 1511 (1974).
9. D. Bloor, R. R. Chance, Eds., Polydiacetylenes: Synthesis, Structure and Electronic Properties, no. 102 of NATO ASI Series E: Applied Sciences (Nijhoff, Dordrecht, 1985).
10. F. W. Fowler, J. W. Lauher, J. Phys. Org. Chem. 13, 850 (2000).
11. J. J. Kane, R. F. Liao, J. W. Lauher, F. W. Fowler, J. Am. Chem. Soc. 117, 12003 (1995).
12. A. Sarkar, S. Okada, H. Matsuzawa, H. Matsuda, H. Nakanishi, J. Mater. Chem. 10, 819 (2000).
13. Y. H. Chan, J. T. Lin, I. W. P. Chen, C. H. Chen, J. Phys. Chem. B 109, 19161 (2005).
14. L. Kavan, Chem. Rev. 97, 3061 (1997).
15. R. B. Heimann, S. E. Evsyukov, L. Kavan, Carbyne and Carbynoid Structures. (Kluwer Academic, Dordrecht, 1999).
16. S. Hino, Y. Okada, K. Iwasaki, M. Kijima, H. Shirakawa, in Nanonetwork Materials: Fullerenes, Nanotubes, and Related Systems, vol. 590 of AIP Conference Proceedings (Springer, New York, 2001), pp. 521-524.
17. T. Gibtner, F. Hampel, J.-P. Gisselbrecht, A. Hirsch, Chem. Eur. J. 8, 408 (2002).
18. S. Eisler et al., J. Am. Chem. Soc. 127, 2666 (2005).
19. Q. Zheng, J. A. Gladysz, J. Am. Chem. Soc. 127, 10508 (2005).
20. J. Hlavatý, J. Rathousky, A. Zukal, L. Kavan, Carbon 39, 53 (2000).
21. A. Baeyer, Ber. Dtsch. Chem. Ges. 18, 2269 (1885).
22. F. Straus, L. Kollek, H. Hauptmann, Ber. Dtsch. Chem. Ges. B. 638, 1886 (1930).
23. E. Heilbronner, V. Hornung, J. P. Maier, E. Kloster-Jensen, J. Am. Chem. Soc. 96, 4252 (1974).
24. J. A. Webb, P.-H. Liu, O. L. Malkina, N. S. Goroff, Angew. Chem. Int. Ed. Engl. 41, 3011 (2002).
25. C. Laurence, M. Queignec-Cabanetos, T. Dziembowska, R. Queignec, B. Wojtkowiak, J. Am. Chem. Soc. 103, 2567 (1981).
26. C. Laurence, M. Queignec-Cabanetos, B. Wojtkowiak, Can. J. Chem. 61, 135 (1983).
27. J. A. Webb, J. E. Klijn, P. A. Hill, J. L. Bennett, N. S. Goroff, J. Org. Chem. 69, 660 (2004).
28. P. D. Rege, O. L. Malkina, N. S. Goroff,;. Am. Chem. Soc. 124, 370 (2002).
29. W. N. Moss, N. S. Goroff, J. Org. Chem. 70, 802 (2005).
30. P. Metrangolo, G. Resnati, Chem. Eur. J. 7, 2511 (2001).
31. A. Crihfield et al., Cryst. Growth Des. 3, 313 (2003).
32. N. S. Goroff, S. M. Curtis, J. A. Webb, F. W. Fowler, J. W. Lauher, Org. Lett. 7, 1891 (2005).
33. H. M. Yamamoto, J. I. Yamaura, R. Kato, Synth. Met. 102, 1448 (1999).
34. H. M. Yamamoto, J. I. Yamaura, R. Kato, Synth. Met. 102, 1515 (1999).
35. Materials and methods are available as supporting material on Science Online.
36. S. Coe et al., J. Am. Chem. Soc. 119, 86 (1997).
37. T. L. Nguyen, F. W. Fowler, J. W. Lauher, J. Am. Chem. Soc. 123, 11057 (2001).
38. For example, in the 2·6 co-crystal, the iodine-nitrogen halogen bonding distance is 3.07 A, and the C-I-N angle is 174.4°. In contrast, the iodine-nitrogen distance in the 1-7 co-crystal is 3.21 Å, and the C-I-N angle is 167.8°. The iodine-oxygen close contact is similar, with a distance of 3.20 Å and angle of 168.5°.
39. 3, Z = 1.
40. We thank N. S. Sampson and H. Tang for their help in measuring the electronic absorption spectrum of PIDA. We are grateful to NSF (grants CHE-9984937, CHE-0446749, and CHE-0453334) for financial support of this research. Crystallographic details for the 1·7 and 2·6 co-crystals are available free of charge from the Cambridge Crystallographic Data Centre under deposition numbers CCDC 294370 and CCDC 294371, respectively.