Conjugated polymers in an arene sandwich

Journal of the American Chemical Society

Volumn 128, Issue 38, 2006, Pages 12426-12427

  McNeil, Anne J ^a   Müller, Peter ^a   Whitten, James E ^b   Swager, Timothy M ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b University of Massachusetts Lowell   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON; POLYMER;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; CONJUGATION; FLUORESCENCE; MOLECULAR WEIGHT; REACTION ANALYSIS; SYNTHESIS;

EID: 33749170802     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0648099     Document Type: Article

References (35)

1. Zheng, J.; Swager, T. M. Adv. Polym. Sci. 2005, 177, 151-179.
2. McQuade, D. T.; Pullen, A. E.; Swager, T. M. Chem. Rev. 2000, 100, 2537-2574.
3. Kulkarni, A. P.; Tonzola, C. J.; Babel, A.; Jenekhe, S. A. Chem. Mater. 2004, 16, 4556-4573.
4. Akcelrud, L. Prog. Polym. Sci. 2003, 28, 875-962.
5. Dennler, G.; Sariciftci, N. S. Proc. IEEE 2005, 93, 1429-1439.
6. Coakley, K. M.; McGehee, M. D. Chem. Mater. 2004, 16, 4533-4542.
7. For recent examples, see: (a) Sun, D.; Rosokha, S. V.; Kochi, J. K. Angew. Chem., Int. Ed. 2005, 44, 5133-5136.
8. (b) Rathore, R.; Chebny, V. J.; Kopatz, E. J.; Guzei, I. A. Angew. Chem., Int. Ed. 2005, 44, 2771-2774.
9. (c) Nakano, T.; Yade, T. J. Am. Chem. Soc. 2003, 125, 15474-15484.
10. (d) Rathore, R.; Abdelwahed, S. H.; Guzei, I. A. J. Am. Chem. Soc. 2003, 125, 8712-8713.
11. (e) Sun, D.-L.; Rosokha, S. V.; Lindeman, S. V.; Kochi, J. K. J. Am. Chem. Soc. 2003, 125, 15950-15963.
12. For recent examples and leading references of segmented conjugated polymers containing paracyclophane, see: (a) Morisaki, Y.; Chujo, Y. Macromolecules 2002, 35, 587-589.
13. (b) Morisaki, Y.; Wada, N.; Chujo, Y. Polymer 2005, 46, 5884-5889.
14. (c) Guyard, L.; Audebert, P.; Dolbier, W. R., Jr.; Duan, J.-X. J. Electroanal. Chem. 2002, 537, 189-193.
15. (d) Salhi, F.; Collard, D. M. Adv. Mater. 2003, 15, 81-85.
16. Some segmented conjugated polymers containing the flexible dithia[3.3]-metacyclophane unit have also been reported. Morisaki, Y.; Ishida, T.; Chujo, Y. Org. Lett. 2006, 8, 1029-1032.
17. Morisaki, Y.; Ishida, T.; Chujo, Y. Polym. J. 2003, 35, 501-506.
18. Electronic conduction has been demonstrated for small molecules incorporating the segmented paracyclophane structure, see: Seferos, D. S.; Trammell, S. A.; Bazan, G. C.; Kushmerick, J. G. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 8821-8825.
19. Continuously conjugated polymers containing dithia[3.3]paracyclophane have been reported. Wang, W.; Xu, J.; Lai, Y.-H.; Wang, F. Macromolecules 2004, 37, 3546-3553.
20. Wang, W.; Xu, J.; Lai, Y.-H. Org. Lett. 2003, 5, 2765-2768.
21. Mataka, S.; Thiemann, T.; Taniguchi, M.; Sawada, T. Synlett 2000, 1211-1227.
22. Mataka, S.; Shigaki, K.; Sawada, T.; Mitoma, V.; Taniguchi, M.; Thiemann, T.; Ohga, K.; Egashira, N. Angew. Chem., Int. Ed. 1998, 37, 2532-2534.
23. Grimme, W., Kämmerling, H. T.; Lex, J.; Gleiter, R.; Heinze, J.; Dietrich, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 205-207.
24. Adapted from the synthesis of Janusene. Cristol, S. J.; Lewis, D. C. J. Am. Chem. Soc. 1967, 89, 1476-1483.
25. Noncovalent π-π-stacking interactions have been shown to influence the selectivity of Diels-Alder cycloadditions. Briggs, J. B.; Miller, G. P. C. R. Chimie 2006, 9, 916-927.
26. Miller, G. P.; Briggs, J. Tetrahedron Lett. 2004, 45, 477-481.
27. 1H NMR spectra. For leading references about the spectroscopic effects of π-π stacking, see: Jones, T. V.; Slutsky, M. M.; Laos, R.; de Greef, T. F. A.; Tew, G. N. J. Am. Chem. Soc. 2005, 127, 17235-17240.
28. Robertson, J. M. Organic Crystals and Molecules; Cornell University Press: Ithaca, New York, 1953; pp 157-160.
29. The TIPS substituents were replaced with hydrogen to simplify the calculations.
30. Frisch, M. J.; et al. Gaussian 03, revision c.02; Gaussian, Inc: Wallingford, CT, 2004.
31. 2 = 0.92 V) are reported relative to the ferrocene/ferricinium ion couple as an internal standard (set to 0.0 V). At this time it is unclear why near identical oxidation potentials are observed for 2b and 3b.
32. The optimized Pd/Cu(I)/benzoquinone-catalyzed polymerization conditions were previously reported, see: Williams, V. E.; Swager, T. M. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 4669-4676.
33. For leading references to discussions on the spectroscopic effects of alkyne-aryl bond rotations, see: (a) Sluch, M. I.; Godt, A.; Bunz, U. H. F.; Berg, M. A. J. Am. Chem. Soc. 2001, 123, 6447-6448.
34. (b) Schmieder, K.; Levitus, M.; Dang, H.; Garcia-Garibay, M. A. J. Phys. Chem. A 2002, 106, 1551-1556.
35. For leading references, see: Kim, Y.; Whitten, J. E.; Swager, T. M. J. Am. Chem. Soc. 2005, 127, 12122-12130.