Philic and phobic segregation in liquid-crystal ionic dendrimers: An enthalpy-entropy competition

Angewandte Chemie - International Edition

Volumn 49, Issue 11, 2010, Pages 1990-1994

  Hernández Ainsa, Silvia ^a   Marcos, Mercedes ^a   Barberá, Joaquín ^a   Serrano, José L ^a  

^a UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

Dendrimers; Frustrated mesophases; Liquid crystals; Supramolecular chemistry; Surface analysis

Indexed keywords

ALKYL CHAIN; FRUSTRATED MESOPHASES; MESOMORPHIC PROPERTY; MESOPHASES; POLY(PROPYLENE IMINE); SUPRAMOLECULAR ORGANIZATIONS;

COMPETITION; CRYSTAL CHEMISTRY; DENDRIMERS; HYDROCARBONS; LIQUID CRYSTALS; MACROMOLECULES; PROPYLENE; SUPRAMOLECULAR CHEMISTRY; SURFACE ANALYSIS;

IONIZATION OF LIQUIDS;

DENDRIMER; IONIC LIQUID; POLYPROPYLENE; POLYPROPYLENEIMINE;

ARTICLE; ATOMIC FORCE MICROSCOPY; CHEMISTRY; CONFORMATION; ENTROPY; X RAY DIFFRACTION;

DENDRIMERS; ENTROPY; IONIC LIQUIDS; MICROSCOPY, ATOMIC FORCE; MOLECULAR CONFORMATION; POLYPROPYLENES; X-RAY DIFFRACTION;

EID: 77949362460     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200905654     Document Type: Article

References (61)

1. a) F. Vögtle, G. Richardt, N. Werner, Dendrimer Chemistry, Wiley-VCH,Weinheim, 2009;
2. b) J. M. J. Fréchet, D. A. Tomalia, Dendrimers and Other Dendritic Polymers, Wiley, Chichester, 2001, and references therein;
3. c) G. R. Newkome, C. N. Moorefield, F. Vögtle, Dendrimers and Dendrons. Concepts, Syntheses, Perspectives, Wiley-VCH, Weinheim, 2001, and references therein.
4. a)W.-D. Jang, K. M. K. Selim, C.-H. Lee, I.-K. Kang, Prog. Polym. Sci. 2009, 34, 1;
5. b) R. Kumar Takede, P. Vijayarai Kumar, N. Kumar Jain, Chem. Rev. 2009, 109, 49;
6. c) I. J. Majoros, J. R. Baker, Jr., Dendrimer-Based Nanomedicine, Pan Stanford Publishing Pte. Ltd. Singapore 596224, 2008;
7. d) B. Klajnert, M. Bryszewska, Dendrimers in Medicine, Nova Science Publishers, New York, 2007;
8. e) U. Boas, J. B. Christensen, P. M. H. Heegaard, Dendrimers in Medicine and Biotechnology, The Royal Society of Chemistry, Cambridge, UK, 2006.
9. a) A. Carlmark, C. Hawker, A. Hulta, M. Malkoch, Chem. Soc. Rev. 2009, 38, 352;
10. b) G. R. Newkome, C. C. Shreiner, Polymer 2008, 49, 1-173;
11. c) C. Gao, D. Yan, Prog. Polym. Sci. 2004, 29, 183;
12. d) J. M. J. Fréchet, J. Polym. Sci. Part A 2003, 41, 3713;
13. e) J. M. J. Fréchet, Proc. Natl. Acad. Sci. USA 2002, 99, 4782;
14. f) J. F. G. A. Jansen, E. M. M. de Brabander-van den Berg, E. W. Meijer, Science 1994, 266, 1226.
15. a) D. K. Smith, A. R. Hirst, C. S. Love, J. G. Hardy, S. V. Brignell, B. Huang, Prog. Polym. Sci. 2005, 30, 220;
16. b) F. Aulenta, W. Hayes, S. Rannard, Eur. Polym. J. 2003, 39, 1741;
17. c) V. Percec, M. Glodde, T. K. Bera, Y. Miura, I. Shiyanovskaya, K. D. Singer, V. S. K. Balagurusamy, P. A. Heiney, I. Schnell, A. Rapp, H.-W. Spiess, S. D. Hudson, H. Duan, Nature 2002, 417, 384.
18. a) M. Marcos, R. Martin-Rapffln, A. Omenat, J. L. Serrano, Chem. Soc. Rev. 2007, 36, 1889;
19. b) B. Donnio, D. Guillon, Adv. Polym. Sci. 2006, 201, 45;
20. c) S. A. Ponomarenko, N. I. Boiko, V. P. Shibaev, Polym. Sci. Ser. C 2001, 43, 1.
21. a) I. Bury, B. Heinrich, C. Bourgogne, D. Guillon, B. Donnio, Chem. Eur. J. 2006, 12, 8396;
22. b) J. M. Rueff, J. Barberá, B. Donnio, D. Guillon, M. Marcos, J. L. Serrano, Macromolecules 2003, 36, 8368.
23. a) R. Martin-Rapffln, M. Marcos, A. Omenat, J. Barberá, P. Romero, J. L. Serrano, J. Am. Chem. Soc. 2005, 127, 7397;
24. b) M. Marcos, R. Alcalá, J. Barberá, P. Romero, C. Sánchez, J. L. Serrano, Chem. Mater. 2008, 20, 5209;
25. c) T. Noguchi, K. Kishikawa, S. Kohmoto, Chem. Lett. 2008, 37, 12;
26. d) K. Binnemans, Chem. Rev. 2005, 105, 4148;
27. e) C. F. J. Faul, M. Antonietti, Adv. Mater. 2003, 15, 673.
28. a) R. Martin-Rapffln, M. Marcos, A. Omenat, J. L. Serrano, E. Taffin de Givenchy, F. Guittard, Liq. Cryst. 2007, 34, 395;
29. b) M. Marcos, R. Martin-Rapffln, A. Omenat, J. Barberá, J. L. Serrano, Chem. Mater. 2006, 18, 1206;
30. c) A. G. Cook, U. Baumeister, C. Tschierske, J. Mater. Chem. 2005, 15, 1708;
31. d) D. Tsiourvas, T. Felekis, Z. Sideratou, C. Paleos, Liq. Cryst. 2004, 31, 739.
32. a) A. I. Stipetic, J.W. Goodby, M. Hird, Y. M. Raoul, H. F. Gleeson, Liq. Cryst. 2006, 33, 819;
33. b) I. M. Saez, J. W. Goodby, J. Mater. Chem. 2005, 15, 26;
34. c) M. Prehm, X. H. Cheng, S. Diele, M. K. Das, C. Tschierske, J. Am. Chem. Soc. 2002, 124, 12072;
35. d) S. Chandrasekar, Handbook of Liquid Crystals, Vol. 2, Wiley-VCH, Weinheim, 1998;
36. e) M. Seitz, T. Plesnivy, K. Schimossek, M. Edelmann, H. Ringsdorf, H. Fischer, H. Uyama, S. Kobayashi, Macromolecules 1996, 29, 6560.
37. a) S. J. Cowling, A.W. Hall, J.W. Goodby, Y. Wang, H. F. Gleeson, J. Mater. Chem. 2006, 16, 2181;
38. b) C. F. J. Faul, M. Antonietti, H. P. Henzte, B. Smarsly, Colloids Surf. A 2003, 212, 115;
39. c) A. F. Thünemann, Prog. Polym. Sci. 2002, 27, 1473;
40. d) K. D'have, P. Rudquist, M. Matuszczyk, S. T. Lagerwall, H. Pauwels, R. Dabrowski, Proc. SPIE-Int. Soc. Opt. Eng. 2000, 33, 3955;
41. e)W. Drzewinski, K. Czuprymski, R. Dabrowski, M. Neubert, Mol. Cryst. Liq. Cryst. 1999, 328, 401;
42. f) A. D. L. Chandani, Y. Ouchi, H. Takezoe, A. Fukuda, Jpn. J. Appl. Phys. 1989, 28, L1261.
43. V. Chechik, M. Zhao, R. M. Crooks, J. Am. Chem. Soc. 1999, 121, 4910.
44. M.W. P. L. Baars, A. J. Karlsson, V. Sorokin, B. F.W. deWaal, E.W. Meijer, Angew. Chem. 2000, 112, 4432; Angew. Chem. Int. Ed. 2000, 39, 4262.
45. a) B. Stark, B. Stühn, H. Frey, C. Lach, K. Lorenz, B. Frick, Macromolecules 1998, 31, 5415;
46. b) K. Lorenz, H. Frey, B. Stühn, R. Mülhaupt, Macromolecules 1997, 30, 6860.
47. D. F. Eaton, B. E. Smart, J. Am. Chem. Soc. 1990, 112, 2821.
48. a) A. Yoshizawa, K. Yamamoto, H. Dewa, I. Nishiyama, J. Yamamoto, H. Yokohama, J. Mater. Chem. 2003, 13, 172;
49. b) M. Kölbel, T. Beyersdorff, X. H. Cheng, C. Tschierske, J. Kain, S. Diele, J. Am. Chem. Soc. 2001, 123, 6809.
50. D. Lose, S. Diele, G. Pelz, E. Dietzmann, W. Weissflog, Liq. Cryst. 1998, 24, 707.
51. a) P. Linse, P. M. Claesson, Macromolecules 2009, 42, 6310;
52. b) R. Pericet-Camara, G. Papastavrou, M. Borkovec, Langmuir 2004, 20, 3264;
53. c) J. Wang, X. Jia, H. Zhong, Y. Luo, X. Zhao, W. Cao, M. L. Wie, Chem. Mater. 2002, 14, 2854.
54. A. C. T. Teixeira, P. Brogueira, A. C. Fernandes, A. M. P. S. G. da Silva, Chem. Phys. Lipids 2008, 153, 98.
55. Similar results have been described in materials that have been deposited by other techniques that imply more ordered deposition, such as spin-coating, Langmuir-Blodgett films, layer-bylayer deposition, or self-assembled monolayers. See, for example: a) I. M. Mahmud, N. Zhou, L. Wang, Y. Zhao, Tetrahedron 2008, 64, 11420;
56. b) S. Chandra, H. Lang, Mater. Chem. Phys. 2009, 114, 926;
57. c) Q. Jiao, Z. Yi, Y. Chen, F. Xi, Polymer 2008, 49, 1520;
58. d) H. G. Abdelhady, S. Allen, M. C. Davies, C. J. Roberts, S. J. B. Tendler, P. M. Williams, Surf. Sci. 2004, 558, 99.
59. a) J. Hu, X-D Xiao,M. Salmeron, Appl. Phys. Lett. 1995, 67, 476;
60. b) I. Díez-Pérez, M. Luna, F. Teherán,D. F. Ogletree, F. Sanz, M. Salmeron, Langmuir 2004, 20, 1284.
61. L. Y. Clasohm, I. U. Vakarelski, R. R. Dagastine, D. Y. C. Chan, G.W. Stevens, F. Grieser, Langmuir 2007, 23, 9335.