The Fluorescent Effects on the N-Substituents of Polyarylenevinylenes Having 1,2-Diphenylmaleimide Moieties

Jun Kyu Lee; Nam Choul Yang; Ho Wook Choi; Dong Hack Suh

Macromolecular Research, Vol.11, No.2, 92-97, April, 2003

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The Fluorescent Effects on the N-Substituents of Polyarylenevinylenes Having 1,2-Diphenylmaleimide Moieties

Jun Kyu Lee, Nam Choul Yang, Ho Wook Choi, and Dong Hack Suh^†

School of Chemical Engineering, Hanyang University, Haengdang-1-Dong, Seongdong-Ku, Seoul 133-791, Korea

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Model compounds and polymers having N-substituted 1,2-diphenylmaleimide moieties were synthesized and characterized by NMR, IR, UV, and fluorescence spectroscopy. The fluorescence intensity could be controlled by N-substituents of model compounds and polymers. As the structure of an N-substituent of them was bulkier, or the electron density of an N-substituent was denser, the photoluminescence intensity was increased. All the compounds showed greenish yellow photoluminescence with the maximum intensity between 510 and 537 nm. From quantum efficiency data of the model compounds and the polymers, the fluorescence intensity of the polymer 11 was higher than that of the model compound 4.

Keywords:N-substituted diphenylmaleimide;fluorescence control;quantum efficiency

[References]

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Phillips D, Polymer Photophysics, D. Phillips, Ed., Chapman and Hall, London (1985)
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Yang NC, Suh DH, Polym. Bull., 46(1), 29 (2001)
Yamamoto T, Osakada K, Wakabayashi T, Yamamoto A, Makromol. Chem. Rapid Commun., 6, 671 (1985)
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[Related Articles]

[1] Potyrailo RA, Hieftje GM, Anal. Chim. Acta, 370, 1 (1998)

[2] Hanafi-Bagby D, Piunno PAE, Wust CC, Krull UJ, Anal. Chim. Acta, 411, 19 (2000)

[3] Goto M, Kawanishi S, Fukumura H, Appl. Surf. Sci., 154, 701 (2000)

[4] Shim HK, Ahn T, Lee HY, Lee JI, Korea Polym. J., 9(2), 116 (2001)

[5] Dirks JB, Photophysics of Aromatic Molecules, Wiley-Interscience, New York (1970)

[6] Phillips D, Polymer Photophysics, D. Phillips, Ed., Chapman and Hall, London (1985)

[7] Piorum D, Parusel ABJ, Rechthaler K, Rotkiewicz K, Kohler G, J. Photochem. Photobiol. A-Chem., 129, 33 (1999)

[8] Chandross EA, Thomas HT, Chem. Phys. Lett., 1, 393 (1971)

[9] Ibemesi JA, El-Bayoumi MA, Kinsinger JB, Chem. Phys. Lett., 53, 270 (1978)

[10] Siemiarczuk A, Ware WR, J. Phys. Chem., 91, 3677 (1987)

[11] Siemiarczuk A, Chem. Phys. Lett., 110, 437 (1984)

[12] Kosower EM, J. Am. Chem. Soc., 107, 1114 (1985)

[13] Kosower EM, Upper D, Annu. Rev. Phys. Chem., 37, 127 (1986)

[14] Sung YK, Yoo MK, Cho CS, Korea Polym. J., 8(1), 26 (2000)

[15] Kapelle S, Rettig W, Lapouyade R, Chem. Phys. Lett., 348, 416 (2001)

[16] Hofkens J, Vosch T, Maus M, Kohn F, Cotlet M, Weil T, Herrmann A, Mullen K, Schryver D, Chem. Phys. Lett., 333, 255 (2001)

[17] Martin E, Weigand R, Chem. Phys. Lett., 288, 52 (1998)

[18] Yang NC, Suh DH, Macromol. Rapid Commun., 22, 335 (2001)

[19] Maahs G, Hegenberg P, Angew. Chem.-Int. Edit., 5, 888 (1966)

[20] Yang NC, Suh DH, Polymer, 42(19), 7987 (2001)

[21] Havelka-Rivard PA, Nagai K, Freeman BD, Sheares VV, Macromolecules, 32(20), 6418 (1999)

[22] Blomquist AT, LaLancette EA, J. Am. Chem. Soc., 83, 1387 (1961)

[23] Yang NC, Suh DH, Polym. Bull., 46(1), 29 (2001)

[24] Yamamoto T, Osakada K, Wakabayashi T, Yamamoto A, Makromol. Chem. Rapid Commun., 6, 671 (1985)

[25] Lakowicz JR, Principles of Fluorescence Spectroscopy, University of Maryland School of Medicine, Batimore, Maryland, Plenum Press (1983)

[26] Eaton DF, Pure Appl. Chem., 60, 1107 (1988)

[27] Isak SJ, Eyring EM, J. Phys. Chem., 96, 1738 (1992)