Luminous polyimide bearing the coumarin 6 chromophore in the side group: Synthesis and fluorescence image patterning

Byung-Sik Park; Woo Yeon Kim; Keun-Byoung Yoon

Korean Journal of Chemical Engineering, Vol.31, No.1, 172-177, January, 2014

DOI10.1007/s11814-013-0210-9 Export Citation

Luminous polyimide bearing the coumarin 6 chromophore in the side group: Synthesis and fluorescence image patterning

Byung-Sik Park, Woo Yeon Kim¹, and Keun-Byoung Yoon^{1, †}

Department of Pharmaceutical Engineering, International University of Korea, Jinju 660-759, Korea
¹Department of Polymer Science, Kyungpook National University, Daegu 702-701, Korea

E-mail:

Coumarin was reacted with polyamic acid to form a luminous polyimide that is highly soluble in organic solvents and displays good thermal stability. Luminous side-chain coumarin 6 polyimide was obtained from incorporation of sulfonated coumarin 6 into polyamic acid. This polymer appeared in reddish brown solids and unusually exhibited a fairly strong visible light-emission of a yellowish green color. Fluorescence image patterning of side-chain coumarin 6 polyimide was successfully conducted by microtransfer molding of the polyamic acid and the subsequent thermal treatment for imidization. The polyimides exhibit high fluorescence, opening the possibility of new applications for these polymers.

Keywords:Polyimide;Coumarin 6;Fluorescence Image Patterning

[References]

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Jung SH, Choi JH, Yang SM, Cho WJ, Ha CS, Mater. Sci. Eng. B., 85, 160 (2001)
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Yoon KB, Jeong S, Kwak G, Macromol. Rapid Commun., 28(11), 1231 (2007)
de Abajo J, Polyimides, in Handbook of Polymer Synthesis, Kricheldorf HR Ed., Vol. 2, Decker, New York (1992)
Yoon KB, Son HJ, Lee DH, J. Korean Ind. Eng. Chem., 17(2), 217 (2006)
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Jones G, Griffin C, Bergmank CY, Bergmank WR, J. Org.Chem., 49, 2705 (1984)
Ohshita J, Uemura T, Kim DH, Kunai A, Kunugi Y, Kakimoto M, Macromolecules, 38(3), 730 (2005)
Min SJ, Park BJ, Kim JM, Macromol. Res., 12(6), 615 (2004)
Coenjarts C, Garcia O, Llauger L, Palfreyman J, Vinette AL, Scaiano JC, J. Am. Chem. Soc., 12, 620 (2003)
Campbell M, Sharp DN, Harrison MT, Denning RG, Turberfield AJ, Nature, 404(6773), 53 (2000)

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[2] Mikami A, Koshiyama T, Tsubokawa T, Jpn. J. Appl. Phys., 44, 608 (2005)

[3] Plater MJ, Greig I, Helfrich MH, Ralston SH, J. Chem.Soc. Perkin Trans., 1, 2553 (2001)

[4] Kurdi J, Tremblay AY, Polymer, 44(16), 4533 (2003)

[5] Lehmann HD, Eberhardt W, Hanack M, J. Membr. Sci., 147(1), 49 (1998)

[6] Jing F, Kareem RA, Srinivasan MP, Mater. Sci. Eng. C., 8-9, 103 (1999)

[7] Jung SH, Choi JH, Yang SM, Cho WJ, Ha CS, Mater. Sci. Eng. B., 85, 160 (2001)

[8] Sakai Y, Ueda M, Yahagi A, Tanno N, Polymer, 43(12), 3497 (2002)

[9] Lee SW, Kim SI, Lee B, Kim HC, Chang TY, Ree M, Langmuir, 19(24), 10381 (2003)

[10] Yoon KB, Jeong S, Kwak G, Macromol. Rapid Commun., 28(11), 1231 (2007)

[11] de Abajo J, Polyimides, in Handbook of Polymer Synthesis, Kricheldorf HR Ed., Vol. 2, Decker, New York (1992)

[12] Yoon KB, Son HJ, Lee DH, J. Korean Ind. Eng. Chem., 17(2), 217 (2006)

[13] Agullo N, Borros S, J. Therm. Anal. Cal., 67, 513 (2002)

[14] Valad-Bubulac T, Hamciuc C, Petreus O, Bruma M, Polym.Adv. Technol., 17, 647 (2006)

[15] Cheng JA, Chang CP, Chen CH, Lin MS, J. Polym. Res., 12, 53 (2005)

[16] Jones G, Griffin C, Bergmank CY, Bergmank WR, J. Org.Chem., 49, 2705 (1984)

[17] Ohshita J, Uemura T, Kim DH, Kunai A, Kunugi Y, Kakimoto M, Macromolecules, 38(3), 730 (2005)

[18] Min SJ, Park BJ, Kim JM, Macromol. Res., 12(6), 615 (2004)

[19] Coenjarts C, Garcia O, Llauger L, Palfreyman J, Vinette AL, Scaiano JC, J. Am. Chem. Soc., 12, 620 (2003)

[20] Campbell M, Sharp DN, Harrison MT, Denning RG, Turberfield AJ, Nature, 404(6773), 53 (2000)