Syntheses of Organic Dyes Based on Phenothiazine as Photosensitizers and Effects of Their π-Conjugated Bridges on the Photovoltaic Performances of Dye-Sensitized Solar Cells

Ki-Hyun Kim; Seung-Min Lee; Min-Hye Seo; Sang-Eun Cho; Won-Pill Hwang; Sung-Hae Park; Young-Keun Kim; Jin-Kook Lee; Mi-Ra Kim

Macromolecular Research, Vol.20, No.2, 128-137, February, 2012

DOI10.1007/s13233-012-0017-2 Export Citation

Syntheses of Organic Dyes Based on Phenothiazine as Photosensitizers and Effects of Their π-Conjugated Bridges on the Photovoltaic Performances of Dye-Sensitized Solar Cells

Ki-Hyun Kim, Seung-Min Lee, Min-Hye Seo, Sang-Eun Cho, Won-Pill Hwang, Sung-Hae Park, Young-Keun Kim, Jin-Kook Lee^†, and Mi-Ra Kim^†

Department of Polymer Science & Engineering, Pusan National University, Busan, 609-735, Korea

E-mail:,

Three organic dyes, 2-cyano-3-(N-hexylphenothiazine-3-yl)acrylic acid (H-PTZ), 2-cyano-3-(5'-(2-(Nhexylphenothiazine-3-yl)vinyl)-2,2'-bithiophen-5-yl)acrylic acid (H-PTZ-BT), and 2-cyano-3-(5-(4-((4-(2-(N-hexylphenothiazine-3-yl)vinyl)phenyl)(phenyl)amino)phenyl)thiophen-2-yl)acrylic acid (H-PTZ-TPA-T), based on the phenothiazine (PTZ) unit as an electron donor moiety and cyanoacrylic acid unit as an electron acceptor moiety were synthesized to study the effect of a π-conjugated bridge of the dye on the performance of the resulting dye-sensitized solar cells devices. The thiophene unit and triphenylamine were introduced as a π-conjugated bridge. The H-PTZTPA-T-sensitized cell showed the highest overall conversion efficiency of 4.01% (Jsc: 9.64 mA·cm^(-2); Voc: 0.69 V;FF: 0.60), while the H-PTZ-sensitized cell showed the lowest value of 3.57% (Jsc: 7.76 mA·cm^(-2); Voc: 0.70 V; FF:0.65) among the cells based on the three organic dyes compared to 5.09% for the cell based on the N719 dye (Jsc:12.77 mA·cm^(-2); Voc: 0.72 V; FF: 0.55) under AM 1.5 illumination (100 mW·cm^(-2)).

Keywords:dyes;photovoltaic effect;phenothiazine;sensitizers;dye-sensitized solar cells.

[References]

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Kalyanasundaram K, Gratzel M, Coord. Chem. Rev., 77, 347 (1998)
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[Referenced By]

[1] Gratzel M, J. Photochem. Photobiol. C., 4, 145 (2003)

[2] Kong FT, Dai SY, Wang KJ, Adv. OptoElectron., 75384 (2007)

[3] Park NG, van de Lagemaat J, Frank AJ, J. Phys. Chem. B, 104(38), 8989 (2000)

[4] Nazeeruddin MK, Kay A, Rodicio I, Humphry-Baker R, Muller E, Liska P, Vlachopoulos N, Gratzel M, J. Am.Chem. Soc., 115, 6382 (1993)

[5] Meng QB, Takahashi K, Zhang XT, Sutanto I, Rao TN, Sato O, Fujishima A, Watanabe H, Nakamori T, Uragami M, Langmuir, 19(9), 3572 (2003)

[6] Robertson N, Angew. Chem. Int. Ed., 45, 2338 (2006)

[7] Hauch A, Georg A, Electrochim. Acta, 46(22), 3457 (2001)

[8] Gratzel M, Acc. Chem. Res., 42, 1788 (2009)

[9] Nazeeruddin MK, De Angelis F, Fantacci S, Selloni A, Viscardi G, Liska P, Ito S, Takeru B, Gratzel MG, J. Am. Chem. Soc., 127(48), 16835 (2005)

[10] Nazeeruddin MK, Pechy P, Renouard T, Zakeeruddin SM, Humphry-Baker R, Comte P, Liska P, Cevey L, Costa E, Shklover V, Spiccia L, Deacon GB, Bignozzi CA, Gratzel M, J. Am. Chem. Soc., 123(8), 1613 (2001)

[11] Gao F, Wang Y, Zhang J, Shi D, Wang M, Humphry-Baker R, Wang P, Zakeeruddin SM, Gratzel M, Chem.Commun., 23, 2635 (2008)

[12] Gao F, Wang Y, Shi D, Zhang J, Wang MK, Jing XY, Humphry-Baker R, Wang P, Zakeeruddin SM, Gratzel M, J. Am. Chem. Soc., 130(32), 10720 (2008)

[13] Ooyama Y, Harima Y, Eur. J. Org. Chem., 18, 2903 (2009)

[14] Sayama K, Tsukagoshi S, Mori T, Hara K, Ohga Y, Shinpou A, Abe Y, Suga S, Arakawa H, Sol. Energy Mater. Sol. Cells, 80(1), 47 (2003)

[15] Lenhard JR, Hein BR, J. Phys. Chem., 100(43), 17287 (1996)

[16] Horiuchi T, Miura H, Uchida S, J. Photochem. Photobiol.A., 164, 29 (2004)

[17] Kim SH, Lee JK, Kang SO, Ko JJ, Yum JH, Fantacci S, Angelis FD, Censo DD, Nazeeruddin MK, Gratzel M, J. Phys. Chem., 128, 16701 (2006)

[18] Ning Z, Tian H, Chem. Commun., 37, 5483 (2009)

[19] Shen P, Liu Y, Huang X, Zhao B, Xiang N, Fei J, Liu L, Wang X, Huang H, Tan S, Dyes. Pigm., 83, 187 (2009)

[20] Cho NR, Choi HB, Kim DH, Song KH, Kang MS, Kang SO, Ko JJ, Tetrahedron., 65, 6236 (2009)

[21] Koumura N, Wang ZS, Mori S, Miyashita M, Suzuki E, Hara K, J. Am. Chem. Soc., 128(44), 14256 (2006)

[22] Wang ZS, Koumura N, Cui Y, Takahashi M, Sekiguchi H, Mori A, Kubo T, Furube A, Hara K, Chem. Mater., 20, 3993 (2008)

[23] Chen R, Yang X, Tian H, Wang X, Hagfeldt A, Sun L, Chem. Mater., 19, 4007 (2007)

[24] Wang ZS, Cui Y, Dan-oh Y, Kasada C, Shinpo A, Hara K, J. Phys. Chem. C., 111, 7224 (2007)

[25] Chena Z, Lia F, Huanga C, Curr. Org. Chem., 11, 1241 (2007)

[26] Mishra A, Fischer MKR, Bauerle P, Angew. Chem.Int. Ed., 48, 2474 (2009)

[27] Hara K, Miyamoto K, Abe Y, Yanagida M, J. Phys. Chem. B, 109(50), 23776 (2005)

[28] Horiuchi T, Miura H, Sumioka K, Uchida S, J. Am. Chem. Soc., 126(39), 12218 (2004)

[29] Hagberg DP, Yum JH, Lee H, De Angelis F, Marinado T, Karlsson KM, Humphry-Baker R, Sun LC, Hagfeldt A, Gratzel M, Nazeeruddin MK, J. Am. Chem. Soc., 130(19), 6259 (2008)

[30] Sayama K, Hara K, Ohga Y, Shinpou A, Suga S, Arakawa H, New J. Chem., 25, 200 (2001)

[31] Chen YS, Li C, Zeng ZH, Wang WB, Wang XS, Zhang BW, J. Mater. Chem., 15, 1654 (2005)

[32] Eu S, Hayashi S, Umeyama T, Oguro A, Kawasaki M, Kadota N, Matano Y, Imahori H, J. Phys. Chem. C., 111, 3528 (2007)

[33] Eu S, Katoh T, Umeyama T, Matano Y, Imahori H, Dalton Trans., 40, 5476 (2008)

[34] Lai G, Bu XR, Santos J, Mintz EA, Synlett., 11, 1275 (1997)

[35] Wang ML, Liu BL, Lin SJ, J. Chin. Inst. Chem. Eng., 38(5-6), 451 (2007)

[36] Suzuki A, J. Organomet. Chem., 576, 147 (1999)

[37] Knoevenagel E, Chem. Ber., 31, 2596 (1898)

[38] Nazeeruddin MK, Zakeeruddin SM, Humphry-Baker R, Jirousek M, Liska P, Vlachopoulos N, Shklover V, Fischer CH, Gratzel M, Inorg. Chem., 38(26), 6298 (1999)

[39] Jung I, Lee JK, Song KH, Song KH, Kang SO, Ko JJ, J. Org. Chem., 72, 3652 (2007)

[40] Hagfeldt A, Gratzel M, Chem. Rev., 95(1), 49 (1995)

[41] Kalyanasundaram K, Gratzel M, Coord. Chem. Rev., 77, 347 (1998)

[42] Hara K, Sato T, Katoh R, Furube A, Ohga Y, Shinpo A, Suga S, Sayama K, Sugihara H, Arakawa H, J. Phys. Chem. B, 107(2), 597 (2003)

[43] Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA, Vreven T, Eds., Gaussian 03, Revision A. 01, Gaussian, Inc., Pittsburgh (2003)

[44] Kern R, Sastrawan R, Ferber J, Stangl R, Luther J, Electrochim. Acta, 47(26), 4213 (2002)

[45] Kuang D, Uchida S, Humphry-Baker R, Zakeeruddin SM, Gratzel M, Angew. Chem. Int. Ed., 47, 1923 (2008)