• Synthesis and Luminescent Characteristics of Anthracene Fluoroionophores
  • Jeon YM, Kim JG, Jang JG, Chang HJ, Kim YS, Gong MS
  • 안트라센 형광 단위를 가지는 Fluoroionophore의 합성 및 발광특성
  • 전영민, 김종규, 장지근, 장호정, 김영섭, 공명선
Abstract
Novel azacrown ether containing blue-light emitting anthracene fluorophore, 9,10-bis[p-(1-aza-18-crown-6)methylphenyl]anthracene (3) and N,N-bis[9-(p-methylphenyl)anthracenylmethyl]-1,6-diaza-18-crown-6 (4) were prepared by reacting anthracene derivatives 1 and 2 with mono- and diaza-18-crown-6, respectively. Also, crown ether containing fluorophore copolymer (5) were prepared by reacting 1,6-diaza-18-crown-6 with 1. Their fluorescence emission spectral studies were investigated by binding group I, group II and various metal cations. The fluorophores showed an absorption at max＝372 nm and an emission at max＝430 nm. pH Dependency of fluoroscence emission intensity were examined to determine the optimum pH for the fluorophores.

Azacrown ether를 포함하는 청색발광 형광체, 9,10-bis[p-(1-aza-18-crown-6)methyl phenyl] anthracene(3)과 N,N-bis[9-(p-methylphenyl)anthracenylmethyl]-1,6-diaza-18-crown-6(4)를 안트라센 유도체 1과 2를 mono- 및 diaza-18-crown-6와 반응시켜 합성하였다. 역시 azacrown ether를 포함하는 형광체 공중합체(5)를 1,6-diaza-18-crown-6와 1을 반응시켜 합성하였다. 제 1족, 2족 그리고 여러 가지 금속 양이온을 결합시킴으로써 형광 발광세기 변화에 대한 연구를 진행하였다. 형광체는 max＝372 nm에서 최대흡수를 그리고 max＝430 nm에서 최대 발광을 보여주었다. 형광체들의 최적 pH 조건을 조사하기 위해 형광 발광 세기의 pH 의존성도 측정하여 하였다.

Keywords: azacrown ether; anthracene fluorophore; fluoroionophore; photoinduced transfer

References
  • 1. Pedersen CJ, J. Am. Chem. Soc., 92, 391 (1970)
  •  
  • 2. Gokel GW, Garcia BJ, Tetrahedron, 4, 317 (1977)
  •  
  • 3. Hamamcl C, Hosgoren H, Erdogan S, Talanta, 47, 229 (1988)
  •  
  • 4. Badaoui FZ, Bourson J, Anal. Chim. Acta, 302, 341 (1995)
  •  
  • 5. Pearson AJ, Hwang JJ, Ignatov ME, Tetrahedron, 42, 3537 (2001)
  •  
  • 6. Jia X, Zhu W, Zhang Y, Yan X, J. Mol. Struct., 604, 159 (2002)
  •  
  • 7. Bronson RT, Bradshaw JS, Savage PB, Fuangswasdi S, Lee SC, Krakowiak KE, Izatt RM, J. Org. Chem., 66, 4752 (2001)
  •  
  • 8. Gutsche CD, Muthukrishnan R, J. Org. Chem., 43, 4905 (1978)
  •  
  • 9. Gutsche CDCalixarenes, Monograph in Supra molecular Chemistry, J. F. Stoddart, Editor, Royal Society of Chemistry, Cambridge, U. K., Vol. 1 (1989)
  •  
  • 10. Ungaro R, Pochini Ain Frontier in Supra molecular Organic Chemistry and Photochemistry, H. J. Schneider, Editor, VCH, Weinheim, Germany, pp 57-81 (1991)
  •  
  • 11. Ji HF, Brown GM, Dabestani R, Chem. Commun., 609 (1999)
  •  
  • 12. Ji HF, Brown GM, Dabestani R, Hettich RL, J. Chem. Soc.-Perkin Trans. 1, 2, 585 (2001)
  •  
  • 13. Valeur B, Leray I, Coor. Chem. Rev., 205, 3 (2000)
  •  
  • 14. Bergonzi R, Fabbrizzi L, Licchelli M, Mangano C, Coor. Chem. Rev., 170, 31 (1998)
  •  
  • 15. Ji HF, Dabestani R, Brown GM, J. Am. Chem. Soc., 122(38), 9306 (2000)
  •  
  • 16. Nakamura Y, Matsumi Y, Zhang W, Kida T, Nakatsumi Y, Lkeda I, Org. Lett., 4, 2641 (2002)
  •  
  • 17. Yang JS, Lin CS, Hwang CY, Org. Lett., 3, 889 (2001)
  •  
  • 18. Shahrisa A, Banaei A, Molecules, 6, 721 (2001)
  •  
  • 19. Xia WS, Schmehl RH, Li CJ, Tetrahedron, 56, 7045 (2000)
  •  
  • 20. Huszthy P, Kontos Z, Vermes B, Pinter A, Tetrahedron, 57, 4967 (2001)
  •  
  • 21. Xue G, Bradshaw JS, Dalley NK, Savage PB, Izatt RM, Prodi L, Montalti M, Zaccheroni N, Tetrahedron, 58, 4809 (2002)
  •  
  • 22. Kawai H, Nagamura T, Mori T, Yoshida K, J. Phys. Chem. A, 6, 660 (1999)
  •  
  • 23. Oguz U, Akkaya EU, Tetrahedron, 39, 5857 (1998)
  •  
  • 24. Alonso MT, Brunet E, Juanes O, Rodriguez-Ubis JC, J. Photochem. Photobiol. A-Chem., 147, 113 (2002)
  •  
  • 25. Chen CT, Huang WP, J. Am. Chem. Soc., 124, 6245 (2002)
  •  
  • 26. Pandya BR, Agrawal YK, Dyes Pigment., 52, 161 (2002)
  •  
  • 27. Kele P, Orbulescu J, Calhoun TL, Gawley RE, Leblanc RL, Tetrahedron, 43, 4413 (2002)
  •  
  • 28. Chang JH, Choi YM, Shin YK, Bull. Korean Chem. Soc., 22, 527 (2001)
  •  
  • 29. Miyaura N, Yanagi T, Suzuki A, Synth. Commun., 11, 513 (1981)
  •  
  • 30. Miyaura N, Yamada K, Suginoma H, Suzuki A, J. Am. Chem. Soc., 107, 972 (1985)
  •  
  • Polymer(Korea) 폴리머
  • Frequency : Bimonthly(odd)
    ISSN 0379-153X(Print)
    ISSN 2234-8077(Online)
    Abbr. Polym. Korea
  • 2024 Impact Factor : 0.6
  • Indexed in SCIE

This Article

  • 2006; 30(5): 426-431

    Published online Sep 25, 2006

  • Received on Jun 14, 2006
  • Accepted on Sep 20, 2006