Molecular design of functionalized m-poly(phenylene ethynylene) foldamers: From simulation to synthesis

Macromolecules

Volumn 43, Issue 14, 2010, Pages 5932-5942

  Nguyen, Ha H ^a   McAliley, James H ^a   Batson, William R ^a   Bruce, David A ^a  

^a AMRL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

APRIORI; BIOMOLECULE SENSING; COMPUTING SYSTEM; DIFFERENT SOLVENTS; EXPERIMENTAL EVIDENCE; EXPERIMENTAL OBSERVATION; FOLDAMERS; FOLDING BEHAVIOR; FUNCTIONALIZED; HELICAL STRUCTURES; MOLECULAR DESIGN; POLY(PHENYLENE ETHYNYLENE)S; POLY(PHENYLENE-ETHYNYLENE); PRIMARY STRUCTURES; SECONDARY STRUCTURES; SIMPLE MODEL; SOLVENT BASED; SYNTHETIC MOLECULES;

ACETONITRILE; AROMATIC COMPOUNDS; CYANIDES; ESTERS; FUNCTIONAL GROUPS; MOLECULAR DYNAMICS;

SOLVENTS;

EID: 77955326923     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma100746x     Document Type: Article

References (62)

1. Nelson, J. C.; Saven, J. G.; Moore, J. S.; Wolynes, P. G. Science 1997, 277 (5333) 1793-1796
2. Lahiri, S.; Thompson, J. L.; Moore, J. S. J. Am. Chem. Soc. 2000, 122, 11315-11319
3. Stone, M. T.; Fox, J. M.; Moore, J. S. Org. Lett. 2004, 6, 3317-3320
4. Stone, M. T.; Heemstra, J. M.; Moore, J. S. Acc. Chem. Res. 2006, 39, 11-20
5. Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893-4011
6. Heemstra, J. M.; Moore, J. S. Org. Lett. 2004, 6, 659-662
7. Adisa, B.; Bruce, D. A. J. Phys. Chem. B 2005, 109, 7548-7556
8. Adisa, B.; Bruce, D. A. J. Phys. Chem. B 2005, 109, 19952-19959
9. Elmer, S. P.; Park, S.; Pande, V. S. J. Chem. Phys. 2005, 123, 114903
10. Elmer, S.; Pande, V. S. J. Phys. Chem. B 2001, 105, 482-485
11. Lee, O. S.; Saven, J. G. J. Phys. Chem. B 2004, 108, 11988-11994
12. Elmer, S. P.; Pande, V. S. J. Chem. Phys. 2004, 121, 12760-12771
13. Elmer, S. P.; Park, S.; Pande, V. S. J. Chem. Phys. 2005, 123, 114902.
14. Hill, D. J.; Moore, J. S. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5053-5057
15. Ray, C. R.; Moore, J. S., Supramolecular Organization of Foldable Phenylene Ethynylene Oligomers. In Poly(Arylene Etynylene)s: From Synthesis to Application, 2005; Vol. 177, pp 91-149.
16. Tan, C. Y.; Pinto, M. R.; Kose, M. E.; Ghiviriga, I.; Schanze, K. S. Adv. Mater. 2004, 16, 1208
17. Podeszwa, R.; Szalewicz, K. Phys. Chem. Chem. Phys. 2008, 10, 2735-2746
18. Sinnokrot, M. O.; Sherrill, C. D. J. Phys. Chem. A 2003, 107, 8377-8379
19. Sinnokrot, M. O.; Sherrill, C. D. J. Am. Chem. Soc. 2004, 126, 7690-7697
20. Tsuzuki, S.; Honda, K.; Uchimaru, T.; Mikami, M.; Fujii, A. J. Phys. Chem. A 2006, 110, 10163-10168
21. Nishio, M.; Hirota, M.; Umezawa, Y. The CH-[pi] interaction: evidence, nature, and consequences; Wiley: New York, 1998; p 217.
22. Arnstein, S. A.; Sherrill, C. D. Phys. Chem. Chem. Phys. 2008, 10, 2646-2655
23. Lee, E. C.; Hong, B. H.; Lee, J. Y.; Kim, J. C.; Kim, D.; Kim, Y.; Tarakeshwar, P.; Kim, K. S. J. Am. Chem. Soc. 2005, 127, 4530-4537
24. Tsuzuki, S.; Honda, K.; Uchimaru, T.; Mikami, M.; Tanabe, K. J. Phys. Chem. A 2002, 106, 4423-4428
25. Sugita, Y.; Okamoto, Y. Chem. Phys. Lett. 1999, 314, 141-151
26. Beck, D. A. C.; White, G. W. N.; Daggett, V. J. Struct. Biol. 2007, 157, 514-523
27. Periole, X.; Mark, A. E. J. Chem. Phys. 2007, 126, 014903.
28. Seibert, M. M.; Patriksson, A.; Hess, B.; van der Spoel, D. J. Mol. Biol. 2005, 354, 173-183
29. Zhang, W.; Wu, C.; Duan, Y., J. Chem. Phys. 2005, 123, 154105.
30. Van der Spoel, D.; Lindahl, E.; Hess, B.; Groenhof, G.; Mark, A. E.; Berendsen, H. J. C. J. Comput. Chem. 2005, 26, 1701-1718
31. Lindahl, E.; Hess, B.; van der Spoel, D. J. Mol. Model. 2001, 7, 306-317
32. Berendsen, H. J. C.; van der Spoel, D.; Vandrunen, R. Comput. Phys. Commun. 1995, 91, 43-56
33. GROMACS USER MANUAL. http://www.gromacs.org/Documentation/Manual.
34. Bekker, H.; Dijkstra, E. J.; Berendsen, H. J. C. Supercomputer 1993, 10 (2) 4-10
35. Hess, B.; Bekker, H.; Berendsen, H. J. C.; Fraaije, J. J. Comput. Chem. 1997, 18, 1463-1472
36. Hukushima, K.; Nemoto, K. J. Phys. Soc. Jpn. 1996, 65, 1604-1608
37. Materials Studio, v. 4.4, Accelrys Software Inc.: San Diego, CA, 2008.
38. Berendsen, H. J. C.; Postma, J. P. M.; Vangunsteren, W. F.; Dinola, A.; Haak, J. R. J. Chem. Phys. 1984, 81, 3684-3690
39. Parrinello, M.; Rahman, A. J. Appl. Phys. 1981, 52, 7182-7190
40. Patriksson, A.; van der Spoel, D. Phys. Chem. Chem. Phys. 2008, 10, 2073-2077
41. Humphrey, W.; Dalke, A.; Schulten, K. J. Mol. Graphics 1996, 14 (1) 33-38
42. Eisenberg, D.; McLachlan, A. D. Nature 1986, 319 (6050) 199-203
43. Eisenhaber, F.; Lijnzaad, P.; Argos, P.; Sander, C.; Scharf, M. J. Comput. Chem. 1995, 16, 273-284
44. High performance computing. http:/citi.clemson.edu/hpc.
45. Jorgensen, W. L.; Maxwell, D. S.; TiradoRives, J. J. Am. Chem. Soc. 1996, 118, 11225-11236
46. Jorgensen, W. L. J. Phys. Chem. 1986, 90, 1276-1284
47. Jorgensen, W. L.; Madura, J. D.; Swenson, C. J. J. Am. Chem. Soc. 1984, 106, 6638-6646
48. Sinnokrot, M. O.; Valeev, E. F.; Sherrill, C. D. J. Am. Chem. Soc. 2002, 124, 10887-10893
49. Lide, D. R.; Kehiaian, H. V. CRC Handbook of Thermophysical and Thermochemical Data; CRC Press: Boca Raton, FL, 1994.
50. Torres, R. B.; Francesconi, A. Z.; Volpe, P. L. O. Fluid Phase Equilib. 2002, 200 (1) 1-10
51. Yang, W. Y.; Prince, R. B.; Sabelko, J.; Moore, J. S.; Gruebele, M. J. Am. Chem. Soc. 2000, 122, 3248-3249
52. Stone, M. T.; Moore, J. S. Org. Lett. 2004, 6, 469-472
53. Adams, H.; Hunter, C. A.; Lawson, K. R.; Perkins, J.; Spey, S. E.; Urch, C. J.; Sanderson, J. M. Chem.-Eur. J. 2001, 7, 4863-4877
54. Cockroft, S. L.; Hunter, C. A.; Lawson, K. R.; Perkins, J.; Urch, C. J. J. Am. Chem. Soc. 2005, 127, 8594-8595
55. Sherrill, D. C., Computations of Noncovalent pi-interactions. In Reviews in computational chemistry; Lipkowitz, K. B.; Boyd, D. B., Eds. Wiley: New York, 2009; Vol. 26, pp 1-30.
56. Arnt, L.; Tew, G. N. J. Am. Chem. Soc. 2002, 124, 7664-7665
57. Prince, R. B.; Saven, J. G.; Wolynes, P. G.; Moore, J. S. J. Am. Chem. Soc. 1999, 121, 3114-3121
58. Carey, F. A.; Sundberg, R. J. Advanced organic chemistry, Part A: Structure and Mechanisms, 5 th ed.; Springer: New York, 2007.
59. Brunsveld, L.; Prince, R. B.; Meijer, E. W.; Moore, J. S. Org. Lett. 2000, 2, 1525-1528
60. Li, C. J.; Slaven, W. T.; Chen, Y. P.; John, V. T.; Rachakonda, S. H. Chem. Commun. 1998, 1351-1352
61. Reichardt, C., Solvents and solvent effects in organic chemistry, 3 rd ed.; Wiley-VCH: Weinheim, Germany, and Cambridge, U.K., 2003; p 640.
62. Blatchly, R. A.; Tew, G. N. J. Org. Chem. 2003, 68, 8780-8785