Synthesis and polymerization behavior of tridentate diacetylene hosts

Journal of Polymer Research

Volumn 13, Issue 2, 2006, Pages 133-144

  Holmes, Brian T ^a   Deb, Prasant ^b   Pennington, William T ^a   Hanks, Timothy W ^b  

^a CLEMSON UNIVERSITY   (United States)

^b FURMAN UNIVERSITY   (United States)

Author keywords

Halogen bonding; Host guest; Polydiacetylene; Polymerization; Topochemical

Indexed keywords

AMINO ACIDS; POLYMERIZATION; SULFUR; SYNTHESIS (CHEMICAL);

HALOGEN BONDING; HOST-GUEST; POLYDIACETYLENE; TOPOCHEMICAL;

ACETYLENE;

EID: 32044453315     PISSN: 10229760     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10965-005-9015-9     Document Type: Article

References (36)

1. Y. Sun, N. J. Taylor and A. J. Carty, Organometallics, 11, 4293 (1992).
2. A. Wong, P. C. W. Kang, C. D. Tage and D. R. Leon, Organometallics, 9, 1992 (1990).
3. P. K. Sahoo and S. K. Swain, J. Polym. Sci., Polym. Chem., 74, 3899 (1999).
4. F. Toda, in: Comprehensive Supramolecular Chemistry, Vol 6, Ch. 15, D. D. MacNicol, F. Toda and R. Bishop, Eds., Elsevier, Oxford, U.K., 1996.
5. For a recent review, see; O. Henze, D. Lentz, A. Schafer, P. Franke and A. D. Schluter, Eur. J. Chem., 8, 357 (2002).
6. For example, see: J. S. Lindsey, J. Org. Chem., 66, 7402 (2001) and references therein.
7. J. Y. Chang, J. R. Yeon, Y. S. Shin, M. J. Man and S.-K. Hong, Chem. Mater., 12, 1076 (2000).
8. D. Phelps, A. Crihfield, J. Hartwell, T. W. Hanks, W. T. Pennington and R. D. Bailey, Mol. Cryst. Liq. Cryst., 354, 1111 (2000).
9. A. Crihfield, J. Hartwell, D. Phelps, R. W. Bailey, W. T. Pennington and T. W. Hanks, Cryst. Growth Des., 3, 313 (2003).
10. T. W. Hanks, W. T. Pennington and R. D. Bailey, in: Anisotropic Organic Materials Approaches to Polar Order, ACS Symp. Ser., Vol. 798, R. Glaser and P. Kaszynski, Eds., 2001, p. 83.
11. R. B. Walsh, C. W. Padgett, P. Metrangolo, G. Resnati, T. W. Hanks and W. T. Pennington, Cryst. Growth Des., 1, 165 (2001).
12. R. D. Bailey, M. Grabarczyk, T. W. Hanks, E. M. Newton and W. T. Pennington, Electronic Conference on Trends in Organic Chemistry (ECTOC-1), H. S. Rzepa and J. M. Goodman, Eds., (CD-ROM), 1995, Royal Society of Chemistry publications. See also http://www.ch.ic.ac.uk/ectoc/papers.
13. W. T. Pennington, R. D. Bailey, B. T. Holmes, L. L. Hook, R. P. Watson, M. Warmoth and T. W. Hanks, Trans. Am. Crystallogr. Assoc. Cryst. Eng. Symp., 33, 145 (1998).
14. J.-H. Lee, M. D. Curtis and J. W. Kampf, Macromolecules, 33, 2136 (2000).
15. H. M. Barentsen, M. van Dijk, H. Zuilhof and E. J. R. Sudholter, Macromolecules, 33, 755 (2000).
16. R. H. Baughman and K. C. Yee, J. Polygr. Sci. Macromol Rev. 13, 248 (1978).
17. Polydiacetylenes, D. Bloor and R. R. Chance, Eds., Martinus Nijhoff, Boston, 1985.
18. Exceptions to this rule have been observed, see: V. Enkelmann, Adv. Polym. Sci., 63, 91 (1984).
19. A. Sarkar and S. S. Talwar, J. Chem. Soc., Perkin Trans. 1, 4141 (1998).
20. B. T. Holmes, W. T. Pennington and T. W. Hanks, Molecules, 7, 447 (2002).
21. The polymerization reaction actually bends the ring out of conjugation with the polymer backbone, but there is still some interaction between the π-syslems. W. H. Kim, N. B. Kodali, J. Kumar and S. K. Tripathy, Macromolecules, 27, 1819, (1994).
22. K. Inoue, A. Ono, Y. Kanehiyo, K. Yanabusa and S. Shinkai, Chem. Lett. 429 (1999).
23. P. Deb, B. T. Holmes, W. T. Pennington and T. W. Hanks, Poly. Prepr. (Am. Chem. Soc. Div. Polym. Chem.), 45, 223 (2004).
24. S. U. Son, B. Y. Kim, C. H. Choi, S. W. Lee, Y. S. Kim and Y. K. Chung Chem. Commun., 2528 (2003).
25. Crystallographically Ordered Polymers, D. J. Sandman, Ed., ACS Symp. Ser. 337, American Chemical Society, Washington, 1987.
26. S. Okada, S. Peng, W. Spevak and D. Charych, Acc. Chem. Res., 31, 229 (1998).
27. B. T. Holmes, C. W. Padgett and W. T. Pennington, Acta Crystallogr., C C58, 0602 (2002).
28. B. Liu and R. Roy, Tetrahedron, 57, 6909 (2001).
29. S. Sarkar, S. Okada, H. Nakanishi and H. Matsuda, Macromolecules, 31, 9174 (1998).
30. H. M. Barntsen, M. van Dijk, P. Kimkes, H. Zuilhof and E. J. R. Sudholter, Macromolecules, 32, 1753 (1999).
31. C. P. Dyer, P. J. Hendra and W. F. Maddams, Spectrochim. Acta, A, 53, 2323 (1997).
32. C. Castiglioni, M. Del Zoppo and G. Zerbi, J. Raman Spectrosc., 24, 485 (1993).
33. For a recent review of Raman investigations into PDAs and PDA crystals with color zones, see: A. Materny, T. Chen, A. Vierheilig and W. Kiefer, J. Raman Spectrosc., 32, 425 (2001).
34. K. Shiga, T. Inocuchi, K. Mori, K. Kondo, K. Kamada, K. Tawa, K. Ohta, T. Maruo, E. Mochizuki and Y. Kai, Macromol. Chem. Phys., 202, 257 (2001).
35. G. N. Patel, R. R. Chance, E. A. Turi and Y. P. Khanna, J. Am. Chem. Soc., 100, 6644 (1978).
36. Note that the monomer spectrum (Figure 8, dashed line) was taken in a quartz cell, while the polymer spectrum was taken through a glass slide. Thus, any peaks below 280 nm analogous to those in the monomer cannot be observed.