Positionally isomeric organic gelators: Structure-gelation study, racemic versus enantiomeric gelators, and solvation effects

Chemistry - A European Journal

Volumn 16, Issue 10, 2010, Pages 3066-3082

  Čaplar, Vesna ^a   Frkanec, Leo ^a   Vujičić, Nataša Šijaković ^a   Žinić, Mladen ^a  

^a RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

Enantiomers fatty acids; Gelation; Racemates; Self assembly

Indexed keywords

ACID CHAINS; ALIPHATIC ACIDS; BI-LAYER; DESCRIPTORS; DIFFERENT STRUCTURE; END GROUPS; FTIR; GEL NETWORKS; GELATION PROPERTIES; GELATOR MOLECULES; GELATORS; HYDROGEN BONDINGS; LOW MOLECULAR WEIGHT; MOLECULAR LEVELS; ORGANIZATIONAL LEVELS; P-XYLENE; PHENYLGLYCINES; POSITIONAL ISOMERS; SODIUM CARBOXYLATE; SOLVATION EFFECT; SPONTANEOUS RESOLUTION; SYNTHETIC OPTIMIZATION; TEM; X-RAY DIFFRACTION STUDIES;

AMINO ACIDS; AROMATIC HYDROCARBONS; CARBOXYLATION; CHIRALITY; COAGULATION; DIFFERENTIAL SCANNING CALORIMETRY; ENANTIOMERS; FATTY ACIDS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; GELS; MOLECULES; ORGANIC ACIDS; SELF ASSEMBLY; SODIUM; SOLVENTS; STEREOCHEMISTRY; XYLENE;

GELATION;

EID: 77649227683     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902342     Document Type: Article

References (80)

1. a) P. Terech. R. G. Weiss (Eds.), Molecular Gels. Springer, Dordrecht, 2006;
2. b) D. K. Smith, Molecular Gels -Nanostructured Soft Materials in Organic Nanostructures (Eds.: J.W. Steed, J. L. Alwood), Wiley-VCH, Weinheim, 2008;
3. c) F. Fages, Top. Curr. Chem. 2005. 256. 1-273;
4. d) P. Terech, R. G. Weiss. Chem. Rev. 1997, 97, 3133-3159:
5. e) J. H. van Esch, B. L. Feringa, Angew. Chem. 2000, 112, 2351-2354;
6. Angew. Chem. Int. Ed. 2000. 39, 2263-2266;
7. f) M. de Loos, B. L. Feringa, J. H. van Esch, Eur. J. Org. Chem. 2005, 3615-3631;
8. g) L. A. Estroff, A. D. Hamilton. Chem. Rev. 2004, 104, 1201-1217.
9. a) R. G. Ellis-Behnke, Y.-X. Liang, S.-W. You, D. K. C. Tay. S. Zhang. K.-F. So. G. E. Schneider. Proc. Natl. Acad. Sci. USA 2006, 103, 5054-5059;
10. b) G. A. Silva. C. Czeisler, K. L. Niece, E. Beniash. D. A. Harrington, J. A. Kessler, S. I. Stupp, Science 2004. 303, 1352-1355;
11. c) Z. Liang, G. Yang, M. Ma, A. S. Abbah, W. W. Lu, B. Xu, Chem. Commun. 2007, 843-845:
12. d) K. J. C. van Bommel. A. Friggeri. S. Shinkai. Angew. Chem. 2003, 115, 1010-1030;
13. Angew. Chem. Int. Ed. 2003, 42, 980-999;
14. e) K. Sada. M. Takeuchi, N. Fujila, M. Numata, S. Shinkai, Chem. Soc. Rev. 2007, 36, 415-435:
15. f) T. Fukushima, K. Asaka, A. Kosaka. T. Aida, Angew. Chem. 2005, 177, 2462-2465;
16. Angew. Chem. Int. Ed. 2005, 44, 2410-2413:
17. g) J. Puigmarti-Luis. V. Laukhin, A. Perez del Pino, J. Vidal-Gancedo, C. Rovira, E. Laukhina, D. B. Amabilino, Angew. Chem. 2007, 119, 242-245:
18. Angew. Chem. Int. Ed. 2007. 46, 238-241;
19. h) P. K. Vemula, G. John. Chem. Commun. 2006. 2218-2220;
20. i) Z. Yang, B. Xu, Chem. Commun. 2004, 2424-2425;
21. j) J. C. Tiller, Angew. Chem. 2003, 115, 3180-3183;
22. Angew. Chem. Int. Ed. 2003. 42, 3072-3075;
23. k) S. V. Vinogradov, T. K. Bronich, A. V. Kabanov, Adv. Drug Delivery Rev. 2002, 54, 135-147.
24. a) P. Jonkheijm, P. van der Schoot, A. P. H.J. Schenning, E. W. Meijer, Science 2006, 313, 80-83;
25. b) D. K. Smith, Chem. Soc. Rev. 2009, 38, 684-694;
26. c) M. de Loos, J. H. van Esch, R. M. Kellogg, B. L. Feringa, Tetrahedron 2007, 63, 7285-7301.
27. J. H. van Esch, Langmuir 2009, 25, 8392-8394.
28. a) A. R. Hirst, I. A. Coates, T. R. Boucheteau, J. F. Miravet, B. Escudei, V. Castelletto, I. W. Hamley, D. K. Smith, J. Am. Chem. Soc. 2008, 130, 9113-9121;
29. b) Y. Jeong, K. Hanabusa, H. Masunga, I. Akiba, K. Miyoshi, S. Sakurai, K. Sakurai, Langmuir 2005, 21, 586-594.
30. a) A. D'Aléo, J.-L. Pozzo, K. Heuzé, F. Vögtle, F. Fages, Tetrahedron 2007, 63, 7482-7488;
31. b) A. D'Aléo, J.-L. Pozzo, F. Fages, M. Schmutz, G. Mieden-Gundert, F. Vögtle, V. Čaplar, M., Žinić, Chem. Commun. 2004, 190-191;
32. c) V. Čaplar, M. Žinić, J.-L. Pozzo, F. Fages, G. Mieden-Gundert, F. Vögtle, Eur. J. Org. Chem. 2004, 4048-4059;
33. d) G. Mieden-Gundert, L. Klein, M. Fischer, F. Vögtle, K. Heuzé, J.-L. Pozzo, M. Vallier, F. Fages, Angew. Chem. 2001, 113, 3266-3267;
34. Angew. Chem. Int. Ed. 2001, 40, 3164-3166.
35. http ://www.vcclab.org/lab/alogps/.
36. N. Zweep, A. Hopkinson, A. Meetsma, W. R. Browne, B. L. Feringa, J. H. van Esch, Langmuir 2009, 25, 8802-8809.
37. a) V. Percec, G. Ungar, M. Peterca, Science 2006, 313, 55-56;
38. b) X. Huang, P. Terech, S. R. Raghavan, R. G. Weiss, J. Am. Chem. Soc. 2005, 127, 4336-4344;
39. c) A. Aggeli, I. A. Nyrkova, M. Bell, R. Harding, L. Carrick, T. C. B. McLeish, A. N. Semenov, N. Boden, Proc. Natl. Acad. Sci. USA 2001, 98, 11857-11862;
40. d) M. de Loos, J. van Esch, R. M. Kellogg, B. L. Feringa, Angew. Chem. 2001, 113, 633-636;
41. Angew. Chem. Int. Ed. 2001, 40, 613-616;
42. e) A. Arnaud, L. Bouteiller, Langmuir 2004, 20, 6858-6863;
43. f) V. Simic, L. Bouteiller, M. Jalabert, J. Am. Chem. Soc. 2003, 125, 13148-13154;
44. g) L. Bouteiller, O. Colombani, F. Lortie, P. Terech, J. Am. Chem. Soc. 2005, 127, 8893-8898;
45. h) J. E. A. Webb, M. J. Crossley, P. Turner, P. Thordarson, J. Am. Chem. Soc. 2007, 129, 7155-7162.
46. a) A. Kentsis, K. L. B. Borden, Curr. Protein Pept. Sci. 2004, 5, 125-134;
47. b) R.B. Martin, Chem. Rev. 1996, 96, 3043-3064;
48. c) D.H. Zhao, J. S. Moore, Org. Biomol. Chem. 2003, 1, 3471-3491.
49. J. Makarević, M. Jokić, B. Perić, V. Tomišić, B. Kojić-Prodić, M. Žinić, Chem. Eur.. J. 2001, 7, 3328-3341.
50. diss,and proved to be the most effective gelator of toluene.
51. a) M. Lescanne, A. Colin, O. Mondain-Monval, F. Fages, J.L. Pozzo, Langmuir 2003, 19, 2013-2020;
52. b)M. Lescanne, P. Grondin, A. d'Aléo, F. Fages, J.-L.Pozzo, O. Mondain-Monval, P. Reinheimer, A. Colin, Langmuir 2004, 40, 3032-3041.
53. a) J. Makarević, M. Jokić, Z. Raza, Z. Š tefanić, B. Kojić-Prodić, M. Žinić, Chem. Eur. J. 2003, 9, 5567-5580;
54. b) A. R. Hirst, D. K. Smith, M. C. Feiters, H. P. M. Geurts, A. C. Wright, J. Am. Chem. Soc. 2003, 125, 9010-9011;
55. c) A. R. Hirst, D. K. Smith, M. C. Feiters, H. P.M. Geurts, Chem. Eur. J. 2004, 10, 5901-5910.
56. a) D. K. Smith, Chem. Soc. Rev. 2009, 38, 684-694;
57. b) A. Brizard, R. Oda, I. Hue, Top. Curr. Chem. 2005, 256, 167-218;
58. c) M. Jokić, J. Makarević, M. Žinić, J. Chem. Soc. Chem. Commun. 1995, 1723-1724;
59. d) R. Oda, I. Hue, Angew. Chem. 1998, 110, 2835-2838;
60. Angew. Chem. Int. Ed. 1998, 37, 2689-2691;
61. e) X. Luo, B. Liu, Y. Liang, Chem. Commun. 2001, 1556-1557;
62. f) K. Hanabusa, H. Kobayashi, M. Suzuki, M. Kimura, H. Shirai, Colloid Polym. Sci. 1998, 276, 252-259;
63. g) K. Hanabusa, K. Okui, K. Karaki, M. Kimura, H. Shirai, J. Colloid Interface Sci. 1997, 195, 86-93;
64. h) S. Bhattacharya, S. N. Ghanashyam Acharya, A. R. Raju, Chem. Commun. 1996, 2101-2102;
65. I) J.-H. Fuhrhop, P. Schneider, J. Rosenberg, E. Boekema, J. Am. Chem. Soc. 1987, 109, 3387-3390.
66. M. Jokić, V. Čaplar, T. Portada, J. Makarević, N. Šijaković-Vujičić, M. Žinić, Tetrahedron Lett. 2008, 50, 509-511.
67. W. Dzwolak, R. Ravindra, C. Nicolini, R. Jansen, R. Winter, J. Am. Chem. Soc. 2004, 126, 3762-3768.
68. TEM investigations of some oxalamide gels have revealed that in the gel samples of the more effective gelators thinner and more flexible fibers could be observed, while with the less effective gelators thicker straight fibers were present.[11,14] It was concluded that thinner and more flexible fibers are capable of forming denser networks having smaller compartments compared to the networks formed by thicker straight fibers; since solvent is immobilized mostly by capillary forces, the former networks should possess higher solvent immobilization capacity than the latter. In this way, the morphology of the gel fibers may also affect the volume of gelled solvent.
69. R. Oda, F. Artzner, M. Laguerre, I. Hue, J. Am. Chem. Soc. 2008, 130, 14705-14712.
70. a) F. Menger, Y. Yamasaki, K. K. Catlin, T. Nishimi, Angew. Chem. 1995, 107, 616-618;
71. Angew. Chem. Int. Ed. Engl. 1995, 34, 585-586;
72. b) D.C. Duncan, D. G. Whitten, Langmuir 2000, 16, 6445-6452;
73. c) B. Escuder, M. Llusar, J. F. Miravet, J. Org. Chem. 2006, 71, 7747-7752.
74. M. Suzuki, T. Sato, A. Kurose, H. Shirai, K. Hanabusa, Tetrahedron Lett. 2005, 46, 2741-2745.
75. a) J. Dong, Y. Ozaki, K. Nakashima, Macromolecules 1997, 30, 1111-1117;
76. b) L. Sun, L. J. Kepley, R. M. Crooks, Langmuir 1992, 8, 2101-2103.
77. A. Pal, Y. K. Ghosh, S. Bhattacharya, Tetrahedron 2007, 63, 7334-7348.
78. SYBYL molecular modeling software of TRIPOS Inc., 1699 South Hanley Road, St. Louis, http://www.tripos.com/.
79. S. Iqbal, J. F. Miravet, B. Escuder, Eur. J. Org. Chem. 2008, 4580-4590.
80. P. Terech, V. Rodriguez, J. D. Barnes, G. B. McKenna, Langmuir 1994, 10, 3406-3418.