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Self-assembly-based Thermo-responsible Luminescent Organogels of Chromophoric L-glutamide-derived Lipids

Published online by Cambridge University Press:  03 March 2011

Taisuke Yamada ,
Mahnaz Derakhshan ,
Hamid Reza Ansarian ,
Makoto Takafuji ,
Hiroshi Hachisako ,
Takashi Sagawa  and
Hirotaka Ihara
Taisuke Yamada
Affiliation:
Department of Applied Chemistry and Biochemistry, Kumamoto University, Kumamoto 860-8555, Japan
Mahnaz Derakhshan
Affiliation:
Department of Applied Chemistry and Biochemistry, Kumamoto University, Kumamoto 860-8555, Japan
Hamid Reza Ansarian
Affiliation:
Department of Applied Chemistry and Biochemistry, Kumamoto University, Kumamoto 860-8555, Japan
Makoto Takafuji
Affiliation:
Department of Applied Chemistry and Biochemistry, Kumamoto University, Kumamoto 860-8555, Japan
Hiroshi Hachisako
Affiliation:
Department of Applied Life Science, Sojo University, Kumamoto 860-0082, Japan
Takashi Sagawa
Affiliation:
Institute of Advanced Energy, Kyoto University, Uji 611-0011, Japan
Hirotaka Ihara*
Affiliation:
Department of Applied Chemistry and Biochemistry, Kumamoto University, Kumamoto 860-8555, Japan
*
a) Address all correspondence to this author. e-mail: ihara@gpo.kumamoto-u.ac.jp
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Abstract

Three lipophilic L-glutamide derivatives with chromophoric head group were synthesized, and their photo-responsive properties were investigated in organic solution systems. By comparing their spectral behaviors, it was shown that organogels underwent a light blue to purple luminescence change, which was triggered by thermally induced monomeric-to-excimeric phase transition. This switching, based on self-assembly, is supposed to have special advantages in molecular electronics.

Keywords

LuminescenceSelf-assemblySol-gel
Type
Articles
Information
Journal of Materials Research , Volume 20 , Issue 9 , September 2005 , pp. 2486 - 2490
Copyright
Copyright © Materials Research Society 2005

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References

REFERENCES

1Terech, P. and Weiss, R.G.: Low-molecular mass gelators of organic liquids and the properties of their gels. Chem. Rev. 97, 3133 (1997).CrossRefGoogle ScholarPubMed
2Van Esch, J.H. and Feringa, B.L.: New functional materials based on self-assembling organogels: From serendipity towards design. Angew. Chem. Int. Ed. Engl. 39, 2263 (2000).3.0.CO;2-V>CrossRefGoogle Scholar
3Ihara, H., Takafuji, M. and Sakurai, T. In Encyclopedia of Nanoscience & Nanotechnology, Vol. 9, edited by Nalwa, H.S. (American Science Publishers, CA, 2004), pp. 473–495.Google Scholar
4Pozzo, J.L., Clavier, G., Rustemeyer, F. and Bouas-Laurent, H.: Photochromic guests in organogels. Mol. Cryst. Liq. Cryst. Sci. Technol. A. 344, 101 (2000).CrossRefGoogle Scholar
5Pozzo, J-L., Clavier, G.M. and Desvergne, J-P.: Rational design of new acid-sensitive organogelators. J. Mater. Chem. 8, 2575 (1998).CrossRefGoogle Scholar
6Maitra, U., Kumar, P.V., Chandra, N., D’Souza, L.J., Prasanna, M.D. and Raju, A.R.: First donor-acceptor interaction promoted gelation of organic fluids. Chem. Commun. 7, 595 (1999).CrossRefGoogle Scholar
7Sagawa, T., Fukugawa, S., Yamada, T. and Ihara, H.: Self-assembled fibrillar networks through highly oriented aggregates of porphyrin and pyrene substituted by dialkyl L-glutamine in organic media. Langmuir 20, 7223 (2002).CrossRefGoogle Scholar
8Ihara, H., Takafuji, M., Sakurai, T., Katsumoto, M., Ushijima, N., Shirosaki, T. and Hachisako, H.: Novel self-assembling organogelators by combination of a double chain-alkylated L-glutamide and a polymeric head group. Org. Biomol. Chem. 1, 3004 (2003).CrossRefGoogle Scholar
9Ihara, H., Takafuji, M., Hirayama, C. and O’Brien, D.F.: Effect of photopolymerization on the morphology of helical supramolecular assemblies. Langmuir 8, 1548 (1992).CrossRefGoogle Scholar
10Nakashima, N., Ando, R., Fukushima, H. and Kunitake, T.: Controlled organization of cyanine and merocyanine dyes at the surface of synthetic bilayer membranes. J. Chem. Soc. Chem. Commun. 12, 707 (1982).CrossRefGoogle Scholar
11Era, M., Hayashi, S., Tsutsui, T., Saito, S., Shimomura, M., Nakashima, N. and Kunitake, T.: Regulation of the aggregated structure of cyanine dyes in Langmuir-Blodgett films using bilayer-forming amphiphiles. Chem. Lett. 1, 53 (1986).CrossRefGoogle Scholar
12Sato, Y. and Woody, R.W.: Circular dichroism of N-phenylnaphthylamine derivatives complexed with the β-form of poly(L-lysine). Biopolymers 19, 2021 (1980).CrossRefGoogle Scholar
13Takafuji, M., Ihara, H., Hirayama, C., Hachisako, H. and Yamada, K.: Functional organic gels chirality induction through formation of highly-oriented structure. Liq. Cryst. 18, 97 (1995).CrossRefGoogle Scholar
14Takafuji, M., Ishiodori, A., Yamada, T., Sakurai, T. and Ihara, H.: Stabilization of enhanced chirality from pyrene-containing L-glutamide lipid in methyl methacrylate by photo-induced polymerization. Chem. Commun. 9, 1122 (2004).CrossRefGoogle Scholar
15Winnik, F.M.: Photophysics of preassociated pyrenes in aqueous polymer solutions and in other organized media. Chem. Rev. 93, 587 (1993).CrossRefGoogle Scholar
16Borsarelli, C.D., Cosa, J.J. and Previtali, C.M.: Interface effect on properties of exciplexes formed between pyrene derivatives and N,N-dimethylaniline in reversed miscelles. Langmuir 9, 2895 (1993).CrossRefGoogle Scholar
17Waka, Y., Mataga, N. and Tanaka, F.: Behavior of heteroexcimer systems in single bilayer liposomes. Photochem. Photobiol. 32, 335 (1980).CrossRefGoogle Scholar
18Hachisako, H., Ihara, H., Kamiya, T., Hirayama, C. and Yamada, K.: Thermal isomerization process in benzene gels of L-glutamic acid-derived lipids with spiropyran head groups. Chem. Commun. 1, 19 (1997).CrossRefGoogle Scholar