Anion-Responsive Supramolecular Dye Chemistry

Supramolecular Soft Matter: Applications in Materials and Organic Electronics

Volumn , Issue , 2011, Pages 97-118

  Maeda, Hiromitsu ^a,b  

^a RITSUMEIKAN UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Anion responsive supramolecular dye chemistry; Charge by charge assemblies; Gelator molecule metal complexation

Indexed keywords

EID: 84886041711     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9781118095331.ch6     Document Type: Chapter

References (88)

1. Israelachvili, J. N. (1992). Intermolecular and Surface Forces. Academic Press, London, p. 450.
2. Hamley, I. W. (2000). Introduction to Soft Matter-Polymers, Colloids, Amphiphiles and Liquid Crystals. John Wiley & Sons, Chichester, p. 342.
3. Flory, P. J. (1974). Gels and gelling process. Faraday Discuss. Chem. Soc., 58 , 7-18.
4. Osada, Y., Khokhlov, A. R., eds. (2001). Polymer Gels and Networks. Marcel Dekker, New York.
5. Siegel, R. A., ed. (2005). Fundamentals and Applications of Polymer Gels. Wiley-VCH, Weinheim.
6. Fages, F., ed. (2005). Low Molecular Mass Gelators, Topics in Current Chemistry. Springer- Verlag, Berlin, Vol. 256 , p. 283.
7. Ishi-i, T., Shinkai, S. (2005). Dye-based organogels: Stimuliresponsive soft materials based on one-dimensional self-assembling aromatic dyes. in Supramolecular Dye Chemistry: Topics in Current Chemistry (Ed.: Ẅurthner, F.), Springer-Verlag, Berlin, Vol. 258 , pp. 119-160.
8. Weiss, R. G., Terech, P., eds. (2006). Molecular Gels. Springer, Dordrecht, p. 978.
9. Terech, P., Weiss, R. G. (1997). Low molecular mass gelators of organic liquids and the properties of their gels. Chem. Rev., 97 , 3133-3159.
10. Abdallah, D. J., Weiss, R. G. (2000). Organogels and low molecular mass organic gelators. Adv. Mater., 12 , 1237-1247.
11. van Esch, J. H., Feringa, B. L. (2000). New functional materials based on self-assembling organogels: From serendipity towards design. Angew. Chem. Int. Ed., 39 , 2263-2266.
12. Sugiyasu, K., Fujita, N., Takeuchi, M., Yamada, S., Shinkai, S. (2003). Proton-sensitive fluorescent organogels. Org. Biomol. Chem., 1 , 895-899.
13. Ghoussoub, A., Lehn, J.-M. (2005). Dynamic sol-gel interconversion by reversible cation binding and release in G-quartet-based supramolecular polymers. Chem. Commun., 5763-5765.
14. Zang, Y., Gu, H., Yang, Z., Xu, B. (2003). Supramolecular hydrogels respond to ligand-receptor interaction. J. Am. Chem. Soc., 125 , 13680-13681.
15. Kabir, S. R., Yokoyama, K., Mihashi, K., Kodama, T., Suzuki, M. (2003). Hyper-mobile water is induced around actin filaments. Biophys. J ., 85 , 3154-3161.
16. Books on anion binding: Bianchi, A., Bowman-James, K., García-España, E., eds. (1997). Supramolecular Chemistry of Anions. Wiley-VCH, New York.
17. Singh, R. P., Moyer, B. A., eds. (2004). Fundamentals and Applications of Anion Separation. Kluwer Academic/Plenum Publishers, New York.
18. Stibor, I., eds. (2005). Anion Sensing, Topics in Current Chemistry. Springer- Verlag, Berlin, Vol. 255 , p. 238.
19. Sessler, J. L., Gale, P. A., Cho, W.-S. (2006). Anion Receptor Chemistry. RSC, Cambridge.
20. Vilar, R., ed. (2008). Recognition of Anions, Structure and Bonding. Springer-Verlag, Berlin.
21. Reviews on anion-responsive supramolecular gels: Maeda, H. (2008). Anion-responsive supramolecular gels. Chem.-Eur. J ., 14 , 11274-11282.
22. Lloyd, G. O., Steed, J. W. (2009). Anion-tuning of supramolecular gel properties. Nat. Chem., 1 , 437-442.
23. Piepenbrock, M.-O. M., Lloyd, G. O., Clarke, N., Steed, J. W. (2010). Metal- and anion-binding supramolecular gels. Chem. Rev., 110 , 1960-2004.
24. Steed, J. W. (2010). Anion-tuned supramolecular gels: a natural evolution from urea supramolecular chemistry. Chem. Soc. Rev., 39 , 3689-3699.
25. For example: Oda, R., Huc, I., Candau, S. J. (1998). Gemini surfactants as new, low molecular weight gelators of organic solvents and water. Angew. Chem. Int. Ed. Engl., 37 , 2689-2691.
26. Yoshida, M., Koumura, N., Misawa, Y., Tamaoki, N., Matsumoto, H., Kawanami, H., Kazaoui, S., Minami, N. (2007). Oligomeric electrolyte as a multifunctional gelator. J. Am. Chem. Soc., 129 , 11039-11041.
27. Tam, A. Y.-Y., Wong, K. M.-C., Wang, G., Yam, V. W.-W. (2007). Luminescent metallogels of platinum (II) terpyridyl complexes: interplay of metal...metal, π-π and hydrophobic-hydrophobic interactions on gel formation. Chem. Commun., 2028-2030.
28. Tam, A. Y.-Y., Wong, K. M.-C., Zhu, N., Wang, G., Yam, V. W.-W. (2009). Luminescent alkynylplatinum( II) terpyridyl metallogels stabilized by Pt...Pt, π-π, and hydrophobic-hydrophobic interactions. Langmuir, 25 , 8685-8695.
29. For example: Kimizuka, N., Nakashima, T. (2001). Spontaneous self-assembly of glycolipid bilayer membranes in sugar-philic ionic liquids and formation of ionogels. Langmuir, 17 , 6759-6761.
30. Webb, J. E. A., Crossley, M. J., Turner, P., Thordarson, P. (2007). Pyromellitamide aggregates and their response to anion stimuli. J. Am. Chem. Soc., 129 , 7155-7162.
31. Dzolic, Z., Cametti, M., Cort, A. D., Mandolini, L., Žinić, M. (2007). Fluoride-responsive organogelator based on oxalamide-derived anthraquinone. Chem. Commun., 34 , 3535-3537.
32. Zhang, Y.-M., Lin, Q., Wei, T.-B., Qin, X.-P., Li, Y. (2009). A novel smart organogel which could allow a two channel anion response by proton controlled reversible sol-gel transition and color changes. Chem. Commun., 6074-6076.
33. Liu, J.-W., Yang, Y., Chen, C.-F., Ma, J.-T. (2010). Novel anion-tuning supramolecular gels with dual-channel response: reversible sol-gel transition and color changes. Langmuir, 26 , 9040-9044.
34. Wang, C., Zhang, D., Zhu, D. (2007). A chiral low-molecular-weight gelator based on binaphthalene with two urea moieties: modulation of the CD spectrum after gel formation. Langmuir, 23 , 1478-1482.
35. Yang, H., Yi, T., Zhou, Z., Zhou, Y., Wu, J., Xu, M., Li, F., Huang, C. (2007). Switchable fluorescent organogels and mesomorphic superstructure based on naphthalene derivatives. Langmuir, 23 , 8224-8230.
36. Kim, T. H., Choi, M. S., Sohn, B.-H., Park, S.-Y., Lyoo, W. S., Lee, T. S. (2008). Gelation-induced fluorescence enhancement of benzoxazole-based organogel and its naked-eye fluoride detection. Chem. Commun., 2364-2366.
37. Teng, M., Kuang, G., Jia, X., Gao, M., Li, Y., Wei, Y. (2009). Glycine-glutamic-acid-based organogelators and their fluoride anion responsive properties. J. Mater. Chem., 19 , 5648-5664.
38. Yamanaka, M., Nakamura, T., Nakagawa, T., Itagaki, H. (2007). Reversible sol-gel transition of a tris-urea gelator that responds to chemical stimuli. Tetrahedron Lett ., 48 , 8990-8993.
39. Stanley, C. E., Clarke, N., Anderson, K. M., Elder, J. A., Lenthall, J. T., Steed, J. W. (2006). Anion binding inhibition of the formation of a helical organogel. Chem. Commun., 3199-3201.
40. Piepenbrock, M.-O. M., Lloyd, G. O., Clarke, N., Steed, J. W. (2008). Gelation is crucially dependent on functional group orientation and may be tuned by anion binding. Chem. Commun., 2644-2646.
41. Applegarth, L., Clark, N., Richardson, A. C., Parker, A. D. M., Radosavljevic-Evans, I., Goeta, A. E., Howard, J. A. K., Steed, J. W. (2005). Modular nanometer-scale structuring of gel fibres by sequential self-organization. Chem. Commun., 5423-5425.
42. 3 carbon, and therefore, the details are omitted in this chapter. Becker, T., Goh, C. Y., Jones, F., McIldowie, M. J., Mocerino, M., Ogden, M. I. (2008). Proline-functionalised calix[4]arene: an anion-triggered hydrogelator. Chem. Commun., 3900-3902.
43. Li, Q., Wang, Y., Li, W., Wu, L. (2007). Structural characterization and chemical response of a Ag-coordinated supramolecular gel. Langmuir, 23 , 8217-8223.
44. Kishimura, A., Yamashita, T., Aida, T. (2005). Phosphorescent organogels via "metallophilic" interactions for reversible RGB-color switching. J. Am. Chem. Soc., 127 , 179-183.
45. Kim, H.-J., Zin, W.-C., Lee, M. (2004). Anion-directed self-assembly of coordination polymer into tunable secondary structure. J. Am. Chem. Soc., 126 , 7009-7014.
46. Kim, H.-J., Lee, J.-H., Lee, M. (2005). Stimuli-responsive gels from reversible coordination polymers. Angew. Chem. Int. Ed., 44 , 5810-5814.
47. Piepenbrock, M.-O. M., Clarke, N., Steed, J. W. (2009). Metal ion and anion-based "tuning" of a supramolecular metallogel. Langmuir, 25 , 8451-8456.
48. Fischer, H., Orth, H. (1934). Die Chemie des Pyrrols. Akademische Verlagsgesellschaft M.B.H., Leipzig.
49. Kadish, K. M., Smith, K. M., Guilard, R., eds. (2000). The Porphyrin Handbook. Academic Press, San Diego, CA,.
50. Kadish, K. M., Smith, K. M., Guilard, R., eds. (2010). Handbook of Porphyrin Science. World Scientific, New Jersey.
51. Maeda, H. (2007). Supramolecular chemistry of acyclic oligopyrroles. Eur. J. Org. Chem., 5313-5325.
52. Maeda, H. (2009). Acyclic oligopyrroles as building blocks of supramolecular assemblies. J. Inclusion Phenom., 64 , 193-214.
53. Maeda, H. (2010). Supramolecular chemistry of pyrrole-based π-conjugated acyclic anion receptors. in Handbook of Porphyrin Science (Eds.: Kadish, K. M., Smith, K. M., Guilard, R.), World Scientific, New Jersey, Vol. 8 , Chapter 38.
54. Maeda, H. (2010). Acyclic oligopyrrolic anion receptors. in Anion Complexation in Supramolecular Chemistry, Topics in Heterocyclic Chemistry (Eds.: Gale, P. A., Dehaen, W.), Springer-Verlag, Berlin, Vol. 24 , pp. 103-144.
55. Maeda, H., Haketa, Y. (2011). Charge-by-charge assemblies based on planar anion receptors. Pure Appl. Chem., 83 , 189-199.
56. Maeda, H., Kusunose, Y. (2005). Dipyrrolyldiketone difluoroboron complexes: novel anion sensors with C-H...X- interactions. Chem.-Eur. J ., 11 , 5661-5666.
57. 3-bridged oligopyrroles. J. Org. Chem., 71 , 2389-2394.
58. 2 complex of fluorinated dipyrrolyldiketone: a new class of efficient receptor for acetate anions. Inorg. Chem., 45 , 8205-8210.
59. 2 Complexes of β-tetraethyl-substituted dipyrrolyldiketones as anion receptors: potential building subunits for oligomeric systems. J. Org. Chem., 72 , 2612-2616.
60. 2 complexes of α-alkyl-substituted dipyrrolyldiketones as acyclic anion receptors. Org. Biomol. Chem., 6 , 433-436.
61. 2 complexes. Synth. Met ., 159 , 792-796.
62. 3-bridged oligopyrroles as anion receptors for formation of supramolecular organogels. J. Am. Chem. Soc., 129 , 13661-13674.
63. 2 complexes as potential building units for oligomeric systems. Org. Biomol. Chem., 6 , 3091-3095.
64. 3-bridged oligopyrroles: potential building subunits of anion-responsive π-conjugated oligomers. Org. Lett ., 10 , 3179-3182.
65. Maeda, H., Eifuku, N. (2009). Alkoxy-substituted derivatives of π-conjugated acyclic anion receptors: effects of substituted positions. Chem. Lett ., 38 , 208-209.
66. Maeda, H., Ito, Y., Haketa, Y., Eifuku, N., Lee, E., Lee, M., Hashishin, T., Kaneko, K. (2009). Solvent-assisted organized structures based on amphiphilic anion-responsive π-conjugated systems. Chem.-Eur. J ., 15 , 3709-3716.
67. Maeda, H., Fujii, R., Haketa, Y. (2010). Supramolecular assemblies derived from formyl-substituted π- conjugated acyclic anion receptors. Eur. J. Org. Chem., 1469-1482.
68. Maeda, H., Terashima, Y., Haketa, Y., Asano, A., Honsho, Y., Seki, S., Shimizu, M., Mukai, H., Ohta, K. (2010). Discotic columnar mesophases derived from 'rod-like' π-conjugated anion-responsive acyclic oligopyrroles. Chem. Commun., 46 , 4559-4561.
69. Maeda, H., Bando, Y., Haketa, Y., Honsho, Y., Seki, S., Nakajima, H., Tohnai, N. (2010). Electronic and optical properties in the solid-state molecular assemblies of anion-responsive pyrrole-based π-conjugated systems. Chem.-Eur. J ., 16 , 11653-11661.
70. Haketa, Y., Maeda, H. (2011). From helix to macrocycle: Anion-driven conformation control of π-conjugated acyclic oligopyrroles. Chem.-Eur. J ., 17 , 1485-1492.
71. Maeda, H., Eifuku, N., Haketa, Y., Ito, Y., Lee, E., Lee, M. (2011). Water-supported organized structures based on wedge-shaped amphiphilic derivatives of dipyrrolyldiketone boron complexes. Phys. Chem. Chem. Phys., 13 , 3843-3850.
72. Maeda, H., Terashima, Y. Solvent-dependent supramolecular assemblies of π-conjugated anion-responsive acyclic oligopyrroles. Chem. Commun., in press. DOI: 10.1039/C1CC12827B.
73. Haketa, Y., Sakamoto, S., Chigusa, K., Nakanishi, T., Maeda, H. Synthesis, Crystal Structures, and Supramolecular Assemblies of Pyrrole-Based Anion Receptors Bearing Modified Pyrrole β-Substituents. J. Org. Chem., in press. DOI: 10.1021/jo2008687.
74. Maeda, H., Kinoshita, K., Naritani, K., Bando, Y. Self-sorting self-complementary assemblies of π-conjugated acyclic anion receptors. Chem. Commun., in press. DOI: 10.1039/C1CC12120K
75. Maeda, H., Kitaguchi, K., Haketa, Y. Anion-responsive covalently linked and metal-bridged oligomers. Submitted.
76. Modifications at a boron unit, substitution by diols and aryl moieties, have also been reported: Maeda, H., Fujii, Y., Mihashi, Y. (2008). Diol-substituted boron complexes of dipyrrolyldiketones as anion receptors and covalently linked 'pivotal' dimers. Chem. Commun., 4285-4287.
77. Maeda, H., Takayama, M., Kobayashi, K., Shinmori, H. (2010). Modification at boron unit: tuning electronic and optical properties of π-conjugated acyclic anion receptors. Org. Biomol. Chem., 8 , 4308-4315.
78. Maeda, H., Bando, Y., Shimomura, K., Yamada, I., Naito, M., Nobusawa, K., Tsumatori, H., Kawai, K. (2011). Chemical-stimuli-controllable circularly polarized luminescence from anion-responsive π-conjugated molecules. J. Am. Chem. Soc., 133 , 9266-9269.
79. Molecular structures along with the assembled modes are also found to be controlled by counter cations: manuscript in preparation.
80. Single-crystal structures of boron-modified derivatives and their anion complexes were also reported. See ref 34 (b) (and (c).
81. Yamamoto, Y., Fukushima, T., Suna, Y., Ishii, N., Saeki, A., Seki, S., Tagawa, S.; Taniguchi, M., Kawai, T., Aida, T. (2006). Photoconductive coaxial nanotubes of molecularly connected electron donor and acceptor layers. Science, 314 , 1761-1764.
82. Yamamoto, Y., Zhang, G., Jin, W., Fukushima, T., Minari, T., Ishii, N., Saeki, A., Seki, S. Tagawa, S., Minari, T. Tsukagoshi, K. Aida, T. (2009). Ambipolar-transporting coaxial nanotubes with a tailored molecular graphene-fullerene heterojunction. Proc. Natl. Acad. Sci. U.S.A, 50 , 21051-21056.
83. Umeyama, T., Tezuka, N., Seki, S., Matano, Y., Nishi, M., Hirao, K., Lehtivuori, H., Tkachenko, V. N., Lemmetyinen, H., Nakao, Y., Sakaki, S., Imahori, H. (2010). Selective formation and efficient photocurrent generation of [70]fullerene-single-walled carbon nanotube composites. Adv. Mater., 22 , 1767-1770.
84. Luisi, P. L., Walde, P., eds. (2000). Giant Vesicles. Wiley-VCH, Chichester.
85. Laursen, B. W., Krebs, F. C. (2000). Synthesis of a triazatriangulenium salt. Angew. Chem. Int. Ed., 39 , 3432-3434.
86. Laursen, B. W., Krebs, F. C. (2001). Synthesis, structure, and properties of azatriangulenium salts. Chem.-Eur. J ., 7 , 1773-1783.
87. Haketa, Y., Sasaki, S., Ohta, N., Masunaga, H., Ogawa, H., Araoka, F., Takezoe, H., Maeda, H. (2010). Oriented salts: dimension-controlled charge-by-charge assemblies from planar receptor-anion complexes. Angew. Chem. Int. Ed., 49 , 10079-10083.
88. Modified anions as TBA salts also provide assembled structures by complexation with planar anion receptors: Maeda, H., Naritani, K., Honsho, Y., Seki, S. (2011). Anion Modules: Building blocks of supramolecular assemblies by combination with π-conjugated anion receptors. J. Am. Chem. Soc., 133 , 8896-8899.