안트라센 형광 단위를 가지는 Fluoroionophore의 합성 및 발광특성

전영민; 김종규; 장지근; 장호정; 김영섭; 공명선; Young-Min Jeon; Jong-Gyu Kim; Ji-Geun Jang; Ho-Jung Chang; Yung-Sup Kim; Myoung-Seon Gong

Polymer(Korea), Vol.30, No.5, 426-431, September, 2006

Export Citation

안트라센 형광 단위를 가지는 Fluoroionophore의 합성 및 발광특성

Synthesis and Luminescent Characteristics of Anthracene Fluoroionophores

전영민, 김종규, 장지근¹, 장호정¹, 김영섭¹, 공명선 ^†

단국대학교 화학과
¹단국대학교 전자공학과

Young-Min Jeon, Jong-Gyu Kim, Ji-Geun Jang¹, Ho-Jung Chang¹, Yung-Sup Kim¹, and Myoung-Seon Gong^†

Department of Chemistry and Institute of Basic Sciences, Dankook University, Chungnam 330-714, Korea
¹Department of Electronic Engineering, Dankook University, Chungnam 330-714, Korea

E-mail:

초록

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.

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.

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

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[Referenced By]

[Related Articles]

[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 CD, Calixarenes, Monograph in Supra molecular Chemistry, J. F. Stoddart, Editor, Royal Society of Chemistry, Cambridge, U. K., Vol. 1 (1989)

[10] Ungaro R, Pochini A, in 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)