研究简报

新型酞菁-苝分子异质结的合成及其光伏性能研究

  • 俞孝伟 ,
  • 张山林 ,
  • 贺伟伟 ,
  • 张志刚 ,
  • 郭丰启 ,
  • 詹传郎 ,
  • 黄彦
展开
  • 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

  网络出版日期: 2012-06-04

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 ,
  • Zhang Shanlin ,
  • He Weiwei ,
  • Zhang Zhigang ,
  • Guo Fengqi ,
  • Zhan Chuanlang ,
  • Huang Yan
Expand
  • 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 date: 2012-03-31

  Revised date: 2012-05-27

  Online published: 2012-06-04

Supported by

Project supported by the National Natural Science Foundation of China (No. 20973182).

摘要

通过酰胺键将酞菁(电子给体单元)和苝二酰亚胺(电子受体单元)偶联, 合成了新型的酞菁-苝分子异质结, 其在二氯甲烷、氯仿、四氢呋喃等常用溶剂中有较好的溶解度. 紫外光谱分析表明其吸收光谱是酞菁和苝二酰亚胺信号的叠加, 出现在300~780 nm之间. 该分子摩尔消光系数高达105 L·mol-1·cm-1数量级, 说明具有较宽的太阳光谱覆盖范围和很高的吸光系数. 基于这些良好的光谱响应特性, 制备了以该分子与[6,6]-苯基-C61-丁酸酸甲酯(PC61BM)为光活性层的有机太阳能电池(OSCs), 该电池器件结构为ITO/聚(3,4-乙撑二氧噻吩):聚苯乙烯磺酸(PEDOT:PSS)/酞菁-苝给受体分子:PC61BM/Ca/Al, 光电转换效率(PCE)为0.009%, 对应的开路电压(Voc)为0.472 V, 短路电流(Jsc)为0.104 mA/cm2, 填充因子(FF)为0.18.

本文引用格式

俞孝伟 , 张山林 , 贺伟伟 , 张志刚 , 郭丰启 , 詹传郎 , 黄彦 . 新型酞菁-苝分子异质结的合成及其光伏性能研究[J]. 有机化学, 2012 , 32(10) : 1981 -1987 . DOI: 10.6023/cjoc201203015

Abstract

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 (Voc) of 0.472 V, a short circuit current (Jsc) of 0.104 mA/cm2 and a fill factor (FF) of 18.2%.

参考文献

[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.

文章导航

/