Synthesis and Photovoltaic Performances of a Novel Phthalocyanine- perylene Molecular Heterojunction

doi:10.6023/cjoc201203015

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (10): 1981-1987.DOI: 10.6023/cjoc201203015 Previous Articles Next Articles

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新型酞菁-苝分子异质结的合成及其光伏性能研究

俞孝伟^a,b, 张山林^b, 贺伟伟^b,c, 张志刚^b, 郭丰启^c, 詹传郎^b, 黄彦^a

a 南京工业大学化学化工学院材料化学工程国家重点实验室南京 210009;
b 中国科学院化学研究所北京分子科学国家实验室中国科学院光化学重点实验室北京 100190;
c 郑州大学化学系光电功能材料实验室郑州 450001

收稿日期:2012-03-31 修回日期:2012-05-27 发布日期:2012-06-04
通讯作者: 郭丰启, 黄彦 E-mail:huangy@njut.edu.cn
基金资助:
国家自然科学基金(No. 20973182)资助项目.

Synthesis and Photovoltaic Performances of a Novel Phthalocyanine- perylene Molecular Heterojunction

Yu Xiaowei^a,b, Zhang Shanlin^b, He Weiwei^b,c, Zhang Zhigang^b, Guo Fengqi^c, Zhan Chuanlang^b, Huang Yan^a

a State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemistry and Chemical Engineering, Nanjing University of Technology, Nanjing 210009;
b Beijing National Laboratory for Molecular Sciences (BNLMS), Laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190;
c Department of Chemistry, Zhengzhou University, Zhengzhou 450001

Received:2012-03-31 Revised:2012-05-27 Published:2012-06-04
Supported by:
Project supported by the National Natural Science Foundation of China (No. 20973182).

A novel phthalocyanine (Pc)-perylene diimide (PDI)-Pc donor-acceptor molecular heterojunction was synthesized through amidation of an asymemetric Pc-carboxylic acid and PDI-diamines, and it is well soluble in common solvent such as dichloromethane, chloroform, and tetrahydrofuran. It shows an broad absorption band covering the whole visible region from 300 to 780 nm, and its molar extinction coefficient reaches as high as 10⁵ L穖ol^-1穋m^-1. Such an adsorption band originates from both the PDI and PC units. Considering the excellent light-harvesting ability, organic solar cells (OSCs) based on the synthetic compound and [6,6]-phenyl-C₆₁-butyric acid methyl ester (PC₆₁BM) were fabricated with the configurations of ITO/poly(3,4-ethylenedioxythiophene):poly-styrenesulfonate (PEDOT:PSS)/phthalocyanine-perylene:PC₆₁BM/Ca/Al. One of the OSC devices showed a power conversion efficiency (PCE) of 0.009% with an open-circuit voltage (V_oc) of 0.472 V, a short circuit current (J_sc) of 0.104 mA/cm² and a fill factor (FF) of 18.2%.

Key words: phthalocyanine, perylene dimide, molecular heterojuntion, photon-to-electron conversion, organic solar cell

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Yu Xiaowei, Zhang Shanlin, He Weiwei, Zhang Zhigang, Guo Fengqi, Zhan Chuanlang, Huang Yan. Synthesis and Photovoltaic Performances of a Novel Phthalocyanine- perylene Molecular Heterojunction[J]. Chin. J. Org. Chem., 2012, 32(10): 1981-1987.

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[1] Zhan, C. L.; Li, A. D. Q. Curr. Org. Chem. 2011, 15, 131.

[2] Chen, Z.; Lohr, A.; Saha-Möller, C. R.; Würthner, F. Chem. Soc. Rev. 2009, 38, 564.

[3] Zang, L.; Che, Y.; Moore, J. S. Acc. Chem. Res. 2008, 41, 1596.

[4] Ke, D. M.; Zhan, C. L.; Xu, S. P.; Ding, X. L.; Peng, A. D.; Sun, J.; He, S. G.; Li, A. D. Q.; Yao, J. N. J. Am. Chem. Soc. 2011, 133, 11022.

[5] Schmidt, R.; Oh, J. H.; Sun, Y.-S.; Deppisch, M.; Krause, A.-M.; Radacki, K.; Braunschweig, H.; Könemann, M.; Bao, P.; Erk, Z. Würthner, F. J. Am. Chem. Soc. 2009, 131, 6215.

[6] Ke, D. M.; Zhan, C. L.; Li, A. D. Q.; Yao, J. N. Angew. Chem., Int. Ed. 2011, 50, 3715.

[7] Schmidt-Mende, L.; Fechtenkötter, A.; Würthner K.; Moons, E.; Friend, R. H.; MacKenzie, J. D. Science 2001, 293, 1119.

[8] Shi, M.-M.; Chen, H.-Z.; Sun, J.-Z.; Ye, J.; Mang, W. Chem. Commun. 2003, 1710.

[9] Li, J.-L.; Dierschke, F.; Wu, J.-S.; Grimsdale, A. C.; Würthner, K. J. Mater. Chem. 2006, 16, 96.

[10] Shin, W. S.; Jeong, H.-H.; Kim, M.-K.; Jin, S.-H.; Kim, M.-R.; Lee, J.-K.; Lee, J. W.; Gal, Y.-S. J. Mater. Chem. 2006, 16, 384.

[11] Mo, X.; Chen, H.-Z.; Wang, Y.; Shi, M.-M.; Wang, M. J. Phys. Chem. B 2005, 109, 7659.

[12] Weitz, R.; Amsharov, T. K.; Zschieschang, U.; Villas, E. B.; Goswami, D. K.; Burghard, M.; Dosch, H.; Jansen, M.; Kern, K.; Klauk, H. J. Am. Chem. Soc. 2008, 130, 4637.

[13] Jones, B. A.; Facchetti, A.; Wasielewski, M. R.; Marks, T. J. J. Am. Chem. Soc. 2007, 129, 15259.

[14] Li, Y.; Tan, L.; Wang, Z.-H.; Qian, H.-L.; Shi, Y.-B.; Hu, W.-P. Org. Lett. 2008, 10, 529.

[15] Hill, Z. B.; Rodovsky, D. B.; Legera, J. M.; Bartholomew, G. P. Chem. Commun. 2008, 6594.

[16] Chen, H. Z.; Ling, M. M.; Mo, X.; Shi, M. M.; Wang, M.; Bao, Z. Chem. Mater. 2007, 19, 816.

[17] Mack, J.; Kobayashi, N. Chem. Rev. 2011, 2, 281.

[18] Claessens, C. G.; Blau, W. J.; Cook, M.; Hanack, M.; Nolte, R. J. M.; Torres, T.; Wöhrle, D. Monatsh. Chem. 2001, 132, 3.

[19] Kolarova, H.; Tomankova, K.; Bajgar, R.; Kolar, P.; Kubinek, R. Ultrasound Med. Biol. 2009, 35, 1397.

[20] Nunes, S. M. T.; Sguilla, F. S.; Tedesco, A. C. Braz. J. Med. Biol. Res. 2004, 37, 273.

[21] Troshin, P. A.; Koeppe, R.; Peregudov, A. S.; Peregudova, S. M.; Egginger, M.; Lyubovskaya, R. N.; Sariciftci, N. S. Chem. Mater. 2007, 19, 5363.

[22] Fischer, M. K. R.; López-Duarte, I.; Wienk, M. M.; Martínez-Díaz, M. V.; Janssen, R. A. J.; Bäuerle, P.; Torres, T. J. Am. Chem. Soc. 2009, 131, 8669.

[23] de la Escosura, A.; Martínez-Díaz, M. V.; Barberá, J.; Torres, T. J. Org. Chem. 2008, 73, 1475.

[24] Kojima, T.; Honda, T.; Ohkubo, K.; Shiro, M.; Kusukawa, T.; Fukuda, T.; Kobayashi, N.; Fukuzumi, S. Angew. Chem., Int. Ed. 2008, 47, 6712.

[25] Zhao, C.; Li, R.; Li, X.; Jiang, J. J. Org. Chem. 2007, 72, 2402.

[26] Yu, X.-W.; Zhan, C.-L.; Huang, Y. Chin. J. Org. Chem. 2012, 32, 770 (in Chinese).

(俞孝伟, 詹传郎, 黄彦, 有机化学, 2012, 32, 770.)

[27] Chao, C. C.; Leung, M. K.; Su, O. Y.; Chiu, K. Y.; Shieh, S. J.; Lin, S. C. J. Org. Chem. 2005. 70, 4323.

[28] Chen, Z.; Baumeister, U.; Tschierske, C.; Würthner, F. Chem. Eur. J. 2007, 13, 450.

[29] Chen, Z.; Stepanenko, V.; Dehm, V.; Prins, P.; Li, D. A.; Seibt, J.; Marquetand, P.; Engel, V.; Würthner, F. Chem. Eur. J. 2007, 13, 436.

[30] Würthner, F.; Thalacker, C.; Diele, S.; Tschierske, C. Chem. Eur. J. 2001, 7, 2245.

[31] Fan, L.; Xu, Y.; Tian, H. Tetrahedron Lett. 2005, 46, 4443.

[32] Li, Y. J.; Wang, N.; Gan, H. Y.; Liu, H. B.; Li, H.; Li, Y. L.; He, X. R.; Huang, C. S.; Gui, S.; Wang, S.; Zhu, D. B. J. Org. Chem. 2005, 70, 9686.

[33] Xu, S. P.; Sun, J.; Ke, D. M.; Song, G.; Zhang, W.; Zhan, C. L. J. Colloid Interface Sci.2010, 349, 142.

[34] Céspedes-Guirao, F. J.; Ohkubo, K.; Fukuzumi, S.; Sastre-Santos, A.; Fernández-Lázaro, F. J. Org. Chem. 2009. 74, 5871.

[35] Li, Y. F.; Cao, Y.; Gao, J.; Wang, D. L.; Yu, G. Heeger, A. J. Synth. Met. 1999, 99, 243.

[36] Scharber, M. C.; Mühlbacher, D.; Koppe, M.; Denk, P.; Waldauf, C.; Heeger, A. J.; Brabec, C. J. Adv. Mater. 2006, 18, 789.

[37] Padinger, F.; Rittberger, R. S.; Sariciftc, I. N. S. Adv. Funct. Mater. 2003, 13, 85.

新型酞菁-苝分子异质结的合成及其光伏性能研究

Synthesis and Photovoltaic Performances of a Novel Phthalocyanine- perylene Molecular Heterojunction

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