디스티릴아릴렌 단위를 포함하는 청색 발광 고분자 형광체의 화학발광 특성

조정현; 이칠원; 공명선

Polymer(Korea), Vol.22, No.5, 714-721, September, 1998

Export Citation

디스티릴아릴렌 단위를 포함하는 청색 발광 고분자 형광체의 화학발광 특성

Chemiluminescent Characteristics of Blue Light-Emitting Polymeric Fluorophores Containing Distyrylarylene Units

조정현, 이칠원, 공명선

초록

화학발광의 형광체로 사용하기 위하여 distyrylarylene 단위를 포함하는 모델 화합물들 4,4''-bis[2-(4-methoxyphenyl)-2-phenylvinyl]benzene (1)과 4,4''-bis[(3,4,5-trimethoxyphenyl)vinyl]benzene (2) 그리고 고분자 형광체들 (3)-(6)을 합성하였다. 이러한 형광체들의 자외선 흡수, 형광 여기, 형광 방출 그리고 366 nm의 자외선 조사에 의한 광발광 스펙트럼을 조사하였으며 최종 화학발광을 측정하였다. TCPO/H₂O₂/sodium benzoate를 사용한 화학발광에서 distyrylarylene 단위를 가지는 모델 화합물들과 중합체들의 발광 파장은 광발광 스펙트럼 그리고 형광 방출 스펙트럼과 유사하였다. 화학발광은 433~440 nm의 파장을 지닌 전형적인 청색 발광을 보여주었다. 화학발광은 혼합 초기 약 5400~5000 mcd/m²의 발광세기를 보여주었으며 30분 그리고 1시간 후에 1200 mcd/m² 그리고 28~30 mcd/m²의 발광세기를 각각 보여주어 화학발광체로서 응용성을 보여주었다.

Distyrylarylene-containing model compounds, 4,4''-bis[2-(4-methoxyphenyl)-2-phenylvinyl]benzene (1) and 4,4''-bis[(3,4,5-trimethoxyphenyl)vinyl]benzene (2), and polymers (3)-(6) were synthesized for a chemiluminescence fluorophore. The UV absorbance, fluorescence excitation and emission, photoluminescence as well as the chemiluminescence characteristics of the model and polymeric fluorophores were measured. Sodium benzoate catalyzed reaction of TCPO with hydrogen peroxide produced a strong chemiluminescent blue light emission with 433 ~ 440nm in the presence of a fluorophore. The wavelength of chemiluminescence light was similar to that of photoluminescence and fluorescent emission. The intensity of chemiluminescent emission showed a 5400 ~ 5000 mcd/m² after mixing the sample and 1200 mcd/m² and 28~30 mcd/m² after 1 hr and 30 min, respectively.

Keywords:chemiluminescence;distyrylarylene derivatives;polymeric fluorophore;photoluminescence

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[1] Chandross EA, Tetrahedron Lett., 761 (1963)

[2] Rauhut MM, Roberts BG, Semsel AM, J. Am. Chem. Soc., 88, 3604 (1966)

[3] Bollyky LJ, Loy M, Roberts BG, Whiteman RH, Iannotta AV, Rauhut MM, Semsel AM, J. Am. Chem. Soc., 89, 6515 (1967)

[4] Bollyky LJ, Roberts BG, Rauhut MM, J. Am. Chem. Soc., 89, 6523 (1967)

[5] Bollyky LJ, Robert BG, Whiteman RH, Lancaster JE, J. Org. Chem., 34, 836 (1969)

[6] Maulding DR, Clarke RA, Roberts BG, Rauhut MM, J. Org. Chem., 33, 250 (1968)

[7] McCapra F, Pure Appl. Chem., 611 (1970)

[8] McCapra F, Prog. Org. Chem., 8, 231 (1973)

[9] McCapra F, Accounts Chem. Res., 9, 206 (1976)

[10] McCapra F, J. Chem. Soc.-Chem. Commun., 946 (1977)

[11] Catherall CLR, Palmer TF, Cundall RB, J. Chem. Soc.-Faraday Trans., 80, 837 (1984)

[12] Lee WY, Chemword, 37(8), 48 (1997)

[13] Miyata S, Nalwa HS, "Organic Electroluminescent Materials and Devices," Gordon and Breach Publishers (1997)

[14] Mark HF, Othmer DF, Overberger CG, Seaborg GT, "Encyclopedia of Chemical Technology," vol. 5, p. 416, John Wiley & Sons, New York (1979)

[15] Sadler SR, Karo W, "Organic Functional Group Preparation," p. 245, Academic Press, New York and London (1968)

[16] McDonald RN, Campbell TW, J. Am. Chem. Soc., 82, 4669 (1960)

[17] Yang Z, Sokolik I, Karasz FE, Macromolecules, 26, 1188 (1993)

[18] Yang Z, Karasz FE, Geise HJ, Macromolecules, 26, 6570 (1993)

[19] Song HS, "Peroxyoxalate Chemiluminescence of Some Polycyclic Aromatic hydrocarbons in a Phthalate Medium," Ph.D. Thesis of Korea University (1987)