Advertisement

Journal of Materials Science

, Volume 43, Issue 4, pp 1366–1375 | Cite as

Preparation and properties of fluoroalkyl end-capped oligomer/fluoresceins nanocomposites

  • Kazuo Sasazawa
  • Yuko Yamada
  • Hideo SawadaEmail author
Article

Abstract

Self-assembled fluorinated oligomeric aggregates formed by fluoroalkyl end-capped N-(1,1-dimethyl-3-oxobutyl)acrylamide oligomers, N,N-dimethylacrylamide oligomers, and acrylic acid oligomers in methanol could recognize selectively fluoresceins as guest molecules to form a new class of fluorinated aggregates/fluoresceins nanocomposites. These fluorinated fluoresceins nanocomposites were found to exhibit an extraordinarily enhanced light absorption (λmax: ca. 440 nm) compared to that (λmaxs: 452 and 480 nm) of the parent fluorescein in the absence of fluorinated aggregates. On the other hand, fluoroalkyl end-capped 2-carboxyethyl acrylate oligomers, which possess no aggregate characteristic in methanol solutions, could not afford such an enhanced light absorption peak under similar conditions. Not only fluorescein but also fluorescein derivatives such fluoresceinamine, carboxyfluorescein, and fluorescein isothiocyanate afforded similar enhanced narrow absorption peaks under similar conditions. Naphthofluorescein was also encapsulated into these fluorinated oligomeric aggregate cores to afford fluorinated aggregates/naphthofluorescein composites, and these fluorinated naphthofluorescein composites afforded an extremely enhanced narrow absorption peak around 520 nm.

Keywords

Methyl Orange DMAA Fluorescein Derivative Oligomeric Aggregate Aggregate Core 

Notes

Acknowledgements

Thanks are due to Kohjin Co., Ltd. and Kyowa Hakko Kogyou Co., Ltd. for supply of DMAA and DOBAA, respectively. The authors also thank Dr. T. Saitoh of Waseda Junior and Senior High School (Tokyo, Japan) for helpful discussion on the ZINDO molecular orbital theoretical studies.

References

  1. 1.
    (a) Ameduri B, Boutevin B (2004) Well-architectured fluoropolymers: synthesis, properties and applications. Elsevier, Amsterdam, p 231; (b) Imae T (2003) Curr Opinion Colloid Interf Sci 8:307Google Scholar
  2. 2.
    (a) Andruzzi L, Chiellini E, Galli G, Li X, Seok SH, Ober CK (2002) J Mater Chem 12:1684; (b) Lacroix-Desmzes P, Delair T, Pichot D, Boutevin B (2000) J Polym Sci, Pt A, Polym Chem 38:3845; (c) Lebreton P, Ameduri B, Boutevin B, Corpart JM (2002) Macromol Chem Phys 203:522; (d) Monteiro MJ, Adamy MM, Leeuwen BJ, Van Herk AM, Destarac M (2005) Macromolecules 38:1538; (e) Ming W, Van de Grampel RD, Gildenpfemmig A, Snijder A, Brongersma HH, Van de Linde R, De With G (2003) Polym Mater Sci Eng 88:517Google Scholar
  3. 3.
    (a) Sawada H, Gong Y-F, Minoshima Y, Matsumoto T, Nakayama M, Kosugi M, Migita T (1992) J Chem Soc, Chem Commun 537; (b) Sawada H, Itoh N, Kawase T, Mitani M, Nakajima H, Nishida M, Moriya Y (1994) Langmuir 10:994; (c) Sawada H, Yoshino Y, Ikematsu Y, Kawase T (2000) Eur Polym J 26:231; (d) Sawada H, Kawase T, Ikematsu Y, Ishii Y, Oue M, Hayakawa Y (1996) Chem Commun 179Google Scholar
  4. 4.
    (a) Sawada H (1996) Chem Rev 96:1779; (b) Sawada H, Kawase T (2001) Kobunshi Ronbunshu 58:147; (c) Sawada H, Kawase T (2001) Kobunshi Ronbunshu 58:255; (d) Sawada H (2000) J Fluorine Chem 105:219Google Scholar
  5. 5.
    (a) Sawada H (2007) Prog Polym Sci 32:509; (b) Sawada H (2007) Polym J 39:637Google Scholar
  6. 6.
    (a) Gong X, Milic T, Xu C, Batteas JD, Drain CM (2002) J Am Chem Soc 124:14290; (b) Takahashi S, Miura H, Kasai H, Okada S, Oikawa H, Nakanishi H (2002) J Am Chem Soc 124:10944; (c) Fu H-B, Yao J-N (2001) J Am Chem Soc 123:1434Google Scholar
  7. 7.
    Sasazawa K, Yamada Y, Fujisawa A, Saitoh T, Ueno K, Oharu K, Sawada H (2005) Colloid Polym Sci 283:812CrossRefGoogle Scholar
  8. 8.
    Sawada H, Yoshino Y, Kurachi M, Kawase T, Takishita K, Tanedani T (2000) Polymer 41:397CrossRefGoogle Scholar
  9. 9.
    (a) Jelly EE (1936) Nature 138:1009; (b) Scheibe G (1936) Angew Chem 49:563Google Scholar
  10. 10.
    (a) Herz AH (1974) Photogr Sci Eng 18:323; (b) Makino S, Kanamaru N, Tanaka J (1980) Bull Chem Soc Jpn 53:3120Google Scholar
  11. 11.
    An B-K, Kwon S-Ki, Jung S-D, Park SY (2002) J Am Chem Soc 124:14410CrossRefGoogle Scholar
  12. 12.
    This work was cited for the following program: Cite this work as: Gaussian 03W, Revision B.02, Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2003) Gaussian, Inc., Pittsburgh PAGoogle Scholar
  13. 13.
    (a) Tamura Z, Morioka T, Maeda M, Tsuji A (1994) Bunseki Kagaku 43:339; (b) Chen S-C, Nakamura H, Tamura Z (1979) Chem Pharm Bull 27:475Google Scholar

Copyright information

© Springer Science+Business Media, LLC 2007

Authors and Affiliations

  1. 1.Central R&D LaboratoriesTaiyo Yuden Co., Ltd.TakasakiJapan
  2. 2.Department of Frontier Materials Chemistry, Graduate School of Science and TechnologyHirosaki UniversityHirosakiJapan

Personalised recommendations