Control of polymer solution structure via intra- and intermolecular aromatic stacking

Macromolecules

Volumn 32, Issue 19, 1999, Pages 6159-6162

  Ilhan, Faysal ^a   Gray, Mark ^a   Blanchette, Keven ^a   Rotello, Vincent M ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC POLYMERS; BINDING ENERGY; CHEMICAL BONDS; ELECTRONS; MACROMOLECULES; SYNTHESIS (CHEMICAL); THERMAL EFFECTS; THERMODYNAMIC STABILITY;

ANTHRACENE; AROMATIC STACKING;

POLYSTYRENES;

EID: 0343244604     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma990724z     Document Type: Article

References (45)

1. (a) Gibney, B. R.; Rabanal, F.; Reddy, K. S.; Dutton, P. L. Biochemistry 1998, 37, 4625-4643.
2. (b) Bowie, U. B. J. Mol. Biol. 1997, 272, 780-789.
3. Varani, G. Acc. Chem. Res. 1997, 30, 189-195.
4. Alivastos, A. P.; Barbara, P. F.; Castleman, A. W.; Chang, J.; Dixon, D. A.; Klein, M. L.; McLendon, G. L.; Miller, J. S.; Ratner, M. A.; Rossky, P. J.; Stupp, S. I.; Thompson, M. E. Adv. Mater. 1998, 10, 1297-1336.
5. (a) Sisson, T. M.; Srisiri, W.; O'Brien, D. F. J. Am. Chem. Soc. 1998, 120 (10), 2322-2329.
6. (b) Ramzi, A.; Prager, M.; Richter, D.; Efstratiadis, V.; Hadjichristidis, N.; Young, R. N.; Allgaier, J. B. Macromolecules 1997, 30, 7171-7182.
7. (c) Edgecombe, B. D.; Stein, J. A.; Fréchet, J. M. J.; Xu, Z.; Kramer, E. J. Macromokcules 1998, 31, 1292-1304.
8. (d) Yang, J. S.; Swager, T. M. J. Am. Chem. Soc. 1998, 120, 11864-11873.
9. (e) Frey, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 2193-2197.
10. (f) Kaifer, E. A. Nature 1993, 364, 484.
11. (g) Lin, H. C.; Lin, Y. S.; Lin, Y. S.; Chao, I.; Li, T. W. Macromolecules 1998, 31, 7298-7311.
12. Hunter, C. A. Chem. Soc. Rev. 1994, 23, 101-109.
13. (a) Burley, S. K.; Petsko, G. A. Adv. Protein Chem. 1988, 39, 125-189.
14. (b) Burley, S. K.; Petsko, G. A. Trends Biotechnol. 1989, 7, 354-359.
15. (a) Hunter, C. A. J. Mol. Biol. 1993, 230, 1025-1054.
16. (b) Saenger, W. Principles of Nucleic Acid Structure; Springer: New York, 1984.
17. (a) Kwon, Y. K.; Chvalun, S. N.; Blackwell, J.; Percec, V.; Heck, J. A. Macromolecules 1995, 28, 1552-1558.
18. (b) Bassani, D. M.; Lehn, J. M.; Baum, G.; Fenske, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 1845-1846.
19. (c)Prince, R. B.; Saven, J. G.; Wolynes, P. G.; Moore, J. S. J. Am. Chem. Soc. 1999, 121, 3114-3121.
20. (d) Yamamoto, T.; Maruyama, T.; Suganuma, H.; Arai, M.; Komarudin, D.; Sasaki, S. Chem. Lett. 1997, 139-140.
21. (e) Kwon, Y. K.;, Danko, C.; Chvalun, S.; Blackwell, J.; Heck, J. A.; Percec, V. Macromol. Symp. 1994, 87, 103-114.
22. (a) Nguyen, J. Q.; Iverson, B. L. J. Am. Chem. Soc. 1999, 121, 2639-2640.
23. (b) Yamamoto, T.; Komarudin, D.; Arai, M.; Lee, B. L.; Suganuma, H.; Asakawa, N.; Inoue, Y.; Kubota, K.; Sasaki, S.; Fukuda, T.; Matsuda, H. J. Am. Chem. Soc. 1998, 120, 139-140.
24. (a) Jin, J. I.; Chung S. J.; Yu S. H. Macromol. Symp. 1998, 79-87.
25. (b) Hurtrez, G.; Dumas, P.; Riess, G. Polym. Bull. 1998, 40, 203-210.
26. (c) Eckert, A. R.; Martin, T. J.; Webber, S. E. J. Phys. Chem. A 1997, 101, 1646-1656.
27. Dupray, L.; Meyer, T. Inorg. Chem. 1996, 35, 6299-6307.
28. Synthesized from corresponding acid via reaction with cyanuric fluoride. For a synthesis of the acid, see: Spivey, A. C.; Bissel, A. J.; Stammen, B. Synth. Commun. 1998 4, 623-632.
29. 3) of 20 ps (300 K) followed by the final 20 ps (300 K) simulation shown in Figure 1. For a description of the solvation method used see: Still, W.; Tempczyk, A.; Hawley, R.; Hendrickson, T. J. Am. Chem. Soc. 1990, 112, 6127-6129.
30. 3) of 20 ps (300 K) followed by the final 20 ps (300 K) simulation shown in Figure 1. For a description of the solvation method used see: Still, W.; Tempczyk, A.; Hawley, R.; Hendrickson, T. J. Am. Chem. Soc. 1990, 112, 6127-6129.
31. (a) Higashi, N.; Takahashi, M.; Niwa, M. Langmuir 1998, 15, 111-115.
32. (b) Spackova, N.; Berger, I.; Egli, M.; Sponer, J. J. Am. Chem. Soc. 1998, 120, 6147-6151.
33. (c) Endo, K.; Ezuhara, T.; Koyanagi, M.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1997, 119, 499-505.
34. (d) Fieser, L. F.; Fieser, M. Reagents for Organic Synthesis; Wiley: New York, 1967; Vol. 1.
35. 1H NMR studies were performed to demonstrate 1·2 complex formation. Addition of polymer 1 to a solution of picric acid (2) resulted in a marked upfield shift of aromatic protons of 2, characteristic of aromatic stacking. For other examples of this behavior, see: (a) Moriuchi, T.; Ikeda, I.; Hirao, T. Organometallics 1995, 14, 3578-3580.
36. (b) Adams, H.; Carver, F. J.; Hunter, C. A.; Morales, J. C.; Seward, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1542-1544.
37. (a) Zubarev, E. R.; Pralle, U. M.; Li, L.; Stupp, S. I. Science 1999, 283, 523-525.
38. (b) Deans, R.; Ilhan, F.; Rotello, V. M. Macromolecules 1999, 32, 4956-4960.
39. -3 M of guest 2. This difference can be explained by the fact that polymer swelling is controlled by multidentate recognition of guest 2 within the preorganized core. In contrast, fluorescence emission will be affected by both the more efficient interactions of picric acid with the core anthracene units, and less efficient interactions with external anthracene moieties.
40. (a) Lehninger, A. L.; Nelson, D. L.; Cox, M. M. Principles of Biochemistry: Worth Pub.: New York, 1993; pp 341-343.
41. (b) Thirumalai, D.; Woodson, S. A. Acc. Chem. Res. 1996, 29, 433-439.
42. Haq, I.; Ladbury, J. E.; Chowdhry, B. Z.; Jenkins, T. C. J. Am. Chem. Soc. 1996, 118, 10693-10701. Mohammadi, S.; Perree-Fauvet, M.; Gresh, N.; Hillairet, K.; Taillandier, E. Biochemistry 1998, 37, 6165-6178. Sartorius, J.; Schneider, H. J. J. Chem. Soc., Perkins Trans 2 1997, 2319-2327.
43. Haq, I.; Ladbury, J. E.; Chowdhry, B. Z.; Jenkins, T. C. J. Am. Chem. Soc. 1996, 118, 10693-10701. Mohammadi, S.; Perree-Fauvet, M.; Gresh, N.; Hillairet, K.; Taillandier, E. Biochemistry 1998, 37, 6165-6178. Sartorius, J.; Schneider, H. J. J. Chem. Soc., Perkins Trans 2 1997, 2319-2327.
44. Haq, I.; Ladbury, J. E.; Chowdhry, B. Z.; Jenkins, T. C. J. Am. Chem. Soc. 1996, 118, 10693-10701. Mohammadi, S.; Perree-Fauvet, M.; Gresh, N.; Hillairet, K.; Taillandier, E. Biochemistry 1998, 37, 6165-6178. Sartorius, J.; Schneider, H. J. J. Chem. Soc., Perkins Trans 2 1997, 2319-2327.
45. 2.