Immobilization of Polyamine Ligands onto a Fluroophore Framework: Their Syntheses and Fluorescent Studies

Juyoung Yoon

Journal of Industrial and Engineering Chemistry, Vol.5, No.3, 212-217, September, 1999

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Immobilization of Polyamine Ligands onto a Fluroophore Framework: Their Syntheses and Fluorescent Studies

Juyoung Yoon^†

Department of Chemistry, Silla University, Pusan 617-736, Korea

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Geometric immobilization of polyamine ligands is expected to change their binding properties toward metal ions. 1,8-Bis(1,4,7-triazacyclononylmethyl) anthracene (10) and 1,8-bis(1,5,9-triaza-cyclododecanylmethyl)anthracene (11) were synthesized from 1,8-bis(bromomethyl)anthracene (7) using appropriate azacrown type compounds. Purification of these compounds based on selective pH extraction methods is described. Chelation-enhanced fluorescence (CHEF) effect was observed when 10 complexed nonquenching metal ions such as Zn(Ⅱ) and Cd(Ⅱ). When compound 10 was titrated with Cu(Ⅱ), wecould obserbe chelation-enhanced quenching(CHEQ) effect in 100% aqueous solution. On the other hand, compound 11 showed no effect on fluorescence by any metal ion examined.

Keywords:fluorescent sensors;anthracene;photoinduced electron transfer;azacrown

[References]

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Czarnik AW, Accounts Chem. Res., 27, 302 (1994)
Desilva AP, Gunaratne HQ, Gunnlaugsson T, Huxley AJ, Mccoy CP, Rademacher JT, Rice TE, Chem. Rev., 97(5), 1515 (1997)
Yoon J, Ohler NE, Vance DH, Aumiller WD, Czarnik AW, Chemosensors of Ion and Molecule Recognition, J.P. Desvergne and A.W. Czarnik Eds., Vol. 492, pp. 189-194, Kluwer, Dordrecht (1997)
Sousa LR, Larson JM, J. Am. Chem. Soc., 99, 307 (1977)
Akkaya EU, Huston ME, Czarnik AW, J. Am. Chem. Soc., 112, 3590 (1990)
Vance DH, Czarnik AW, J. Am. Chem. Soc., 116(20), 9397 (1994)
Rehm D, Weller A, Isr. J. Chem., 8, 259 (1970)
Julliard M, Chanon M, Chem. Br., 558 (1982)
deSilva AP, Gunaratne HQN, McCoy CP, J. Am. Chem. Soc., 119(33), 7891 (1997)
Pietraskiewics M, Comprehensive Supramolecular Chemistry, D.N. Reinhoudt and J.M. Lehn Eds., vol. 10, pp. 225-266, Elsevier, London (1996)
Spiro TG, Zinc Enzymes, Wiley, New York (1983)
Breslow R, Singh S, Bioorg. Chem., 16, 408 (1988)
Zompa LJ, Inorg. Chem., 17, 2531 (1978)
Yoon J, Ph.D. Thesis, The Ohio State University, U.S.A. (1994)
Ohler NE, M.S. Thesis, The Ohio State University, U.S.A. (1993)
McAuley A, Norman PR, Olubuyide O, Inorg. Chem., 23, 1938 (1984)
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Akiyama S, Misumi S, Nakagawa M, Bull. Chem. Soc. Jpn., 1829 (1962)
Akiyama S, Nakagawa M, Bull. Chem. Soc. Jpn., 44, 3158 (1971)
Vance DH, Ph.D. Thesis, The Ohio State University, U.S.A. (1993)
Zompa LJ, Inorg. Chem., 17, 2531 (1978)
Arishima T, Hamada K, Takmoto S, Nippon Kag. Kaishi, 1119 (1973)
Watanabe N, Ohe S, Takmoto S, Nippon Kag. Kaishi, 298 (1975)
DeRonde M, Driscoll D, Yang R, Zompa LJ, Inorg. Nucl. Chem. Lett., 11, 521 (1975)
Vance DH, Czarnik AW, J. Am. Chem. Soc., 115, 12165 (1993)
Thiem HJ, Brundle M, Breslow R, J. Am. Chem. Soc., 110, 8612 (1988)
Breslow R, Chung S, Tetrahedron Lett., 31, 631 (1990)

[1] Czarnik AW, Fluorescent Chemosensors for Ion and Molecule Recognition, A.W. Czarnik Ed., pp. 104-129, American Chemical Society, Washington D.C. (1993)

[2] Czarnik AW, Accounts Chem. Res., 27, 302 (1994)

[3] Desilva AP, Gunaratne HQ, Gunnlaugsson T, Huxley AJ, Mccoy CP, Rademacher JT, Rice TE, Chem. Rev., 97(5), 1515 (1997)

[4] Yoon J, Ohler NE, Vance DH, Aumiller WD, Czarnik AW, Chemosensors of Ion and Molecule Recognition, J.P. Desvergne and A.W. Czarnik Eds., Vol. 492, pp. 189-194, Kluwer, Dordrecht (1997)

[5] Sousa LR, Larson JM, J. Am. Chem. Soc., 99, 307 (1977)

[6] Akkaya EU, Huston ME, Czarnik AW, J. Am. Chem. Soc., 112, 3590 (1990)

[7] Vance DH, Czarnik AW, J. Am. Chem. Soc., 116(20), 9397 (1994)

[8] Rehm D, Weller A, Isr. J. Chem., 8, 259 (1970)

[9] Julliard M, Chanon M, Chem. Br., 558 (1982)

[10] deSilva AP, Gunaratne HQN, McCoy CP, J. Am. Chem. Soc., 119(33), 7891 (1997)

[11] Pietraskiewics M, Comprehensive Supramolecular Chemistry, D.N. Reinhoudt and J.M. Lehn Eds., vol. 10, pp. 225-266, Elsevier, London (1996)

[12] Spiro TG, Zinc Enzymes, Wiley, New York (1983)

[13] Breslow R, Singh S, Bioorg. Chem., 16, 408 (1988)

[14] Zompa LJ, Inorg. Chem., 17, 2531 (1978)

[15] Yoon J, Ph.D. Thesis, The Ohio State University, U.S.A. (1994)

[16] Ohler NE, M.S. Thesis, The Ohio State University, U.S.A. (1993)

[17] McAuley A, Norman PR, Olubuyide O, Inorg. Chem., 23, 1938 (1984)

[18] Akiyama S, Misumi S, Nakagawa M, Bull. Chem. Soc. Jpn., 35, 1826 (1962)

[19] Akiyama S, Misumi S, Nakagawa M, Bull. Chem. Soc. Jpn., 1829 (1962)

[20] Akiyama S, Nakagawa M, Bull. Chem. Soc. Jpn., 44, 3158 (1971)

[21] Vance DH, Ph.D. Thesis, The Ohio State University, U.S.A. (1993)

[22] Zompa LJ, Inorg. Chem., 17, 2531 (1978)

[23] Arishima T, Hamada K, Takmoto S, Nippon Kag. Kaishi, 1119 (1973)

[24] Watanabe N, Ohe S, Takmoto S, Nippon Kag. Kaishi, 298 (1975)

[25] DeRonde M, Driscoll D, Yang R, Zompa LJ, Inorg. Nucl. Chem. Lett., 11, 521 (1975)

[26] Vance DH, Czarnik AW, J. Am. Chem. Soc., 115, 12165 (1993)

[27] Thiem HJ, Brundle M, Breslow R, J. Am. Chem. Soc., 110, 8612 (1988)

[28] Breslow R, Chung S, Tetrahedron Lett., 31, 631 (1990)