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最近在与师弟师妹的讨论中发现他们对于ICBA这个非常优秀的材料的历史不了解，毕竟他们都是物理和电子学背景的，对有机电子学的合成部分，凡是涉及到分子式的就一概略过了。特写一个简单的文章，希望对师弟师妹们有所帮助 。

Chinese Version

ICBA于1997年第一次合成得到的；2008年第一次用于太阳能电池，效率为5.1%，可惜被申请了专利；2010年何有军师兄在很多富勒烯衍生物中筛选出ICBA这个分子，并且成功优化到5.44%, 赵师兄进一步优化到了6.5%,之后他们组对ICBA及相关衍生物进行了一系列的优化和系统性研究。

ICBA是一个非常优秀的材料，因为它的易制备，高溶解性，高LUMO值，高Voc值等，近几年对其及衍生进行了大量的研究，如三元体系，电荷转移，倒置电池等。

缺点是

1）ICBA及相关早被申请了大量的专利

2）LUMO太高，与很多聚合物的能级不匹配，只与P3HT有很好的效果。

         窃以为，如果有LUMO值高于PCBM在0.05~0.12eV，且是少于4个的富勒烯C60衍生物的会非常有前途，不过我还有找到，同时也没有别人找到 :(

PCBM是1995年第一次被Wuld合成出来¹，俞刚第一次将其与MEH-PPV共混得到2.9%的效率²，PCBM的广泛研究中，Wuld的文章一直是被提到的，同样对ICBA的研究中，Neilands³和Laird^4,5的铺垫性工作也是需要提到的，我们的每一份学术成果都是踏在前辈的脚印和尸体上。

English Version

ICBA, Indene C60 Bi adduct.

茚与C60双加成物

History of ICBA (Indene C60 Biadduct) from synthesis, application, opimization.

ICBA was a very excellent [60]fullerene material,  which was easy to prepare, high solubility, high LUMO level and high Voc. It's was firstly synthesis in 1997, first application in OPV in 2009, first opimization with PCE=5.44% in2010. Much study have been done after ICBA's reexplorer in 2010 by Dr. He You-jun and Prof. Dr. Li Yong-fang, such as, e.g. ternary material, charge transfer, inverted cells.

Below is its detailed history.

1)   C60>>>ICBA, Ref³

First synthesis of ICBA in 1997

2)   ICBA>>>太阳能电池 PCE=5.1%,专利Ref^4,5

ICBA's First Application in organic photovoltaic in 2008, patent.

3)   ICBA用于太阳能电池的优化，PCE=5.44%, Ref⁶

Optimization of ICBA in OPV in 2010

4)   ICBA用于太阳能电池的进一步优化，PCE=6.5%， Ref⁷

Further Optimization of ICBA

5)   [70]ICBA用于太阳能电池, PCE=5.79%, Ref⁸

[70]ICBA's first application in OPV

6)   将MoO3取代PEDOT:PSS，[70]ICBA的器件优化,Ref⁹

[70]ICBA's application in OPV with MoO3 instead of PEDOT:PSS in 2012

7)     ICBA相关文章，自从2010年李永舫老师和何有军师兄发掘了ICBA这个非常优秀的材料易制备，高溶解性，高LUMO值和高Voc值后，业界对其做了大量的研究，做了很多相关研究，如三元体，电荷转移，倒置电池等。，Ref^10-16

Much study have been done after ICBA's reexplorer in 2010 by Dr. He You-jun and Prof. Dr. Li Yong-fang, such as ease to prepare, high solubility, high LUMO level and high Voc, e.g. ternary material, charge transfer, inverted cells.

Topliuchao@gmail.com

2012-2-11 9:46:32

References:

(1)    J. C. Hummelen, B. W. Knight, F. Lepeq, F. Wudl, J. Yao, C. L. Wilkins, "PREPARATION AND CHARACTERIZATION OF FULLEROID AND METHANOFULLERENE DERIVATIVES", Journal of Organic Chemistry, 1995, 60, 532.

(2)    G. Yu, J. Gao, J. C. Hummelen, F. Wudl, A. J. Heeger, "Polymer Photovoltaic Cells: Enhanced Efficiencies via a Network of Internal Donor-Acceptor Heterojunctions", Science, 1995, 270, 1789.

(3)    Austris Puplovskis, Janis Kacens, Ojars Neilands, "New route for [60]fullerene functionalisation in [4+2] cycloaddition reaction using indene", Tetrahedron Letters, 1997, 38, 285.

(4)    Darin W. Laird, Reza Stegamat, Henning Richter, Viktor Vejins, Larry Scott, Lada; Thomas A., "ORGANIC PHOTOVOLTAIC DEVICES COMPRISING FULLERENES AND DERIVATIVES THEREOF", 2008,WO/2008/018931.

(5)    Darin W. Laird, Henning Richter, Viktor Vejins, Lowrence Scott, Lada; Thomas A., Reza Stegamat, Daadi Malika, "Organic photovoltaic devices comprising fullerenes and derivatives thereof and improved methods of making fullerene derivatives", 2009,WO2009086210A2.

(6)    Y. J. He, H. Y. Chen, J. H. Hou, Y. F. Li, "Indene-C-60 Bisadduct: A New Acceptor for High-Performance Polymer Solar Cells", Journal of the American Chemical Society, 2010, 132, 1377.

(7)    Guangjin Zhao, Youjun He, Yongfang Li, "6.5% Efficiency of Polymer Solar Cells Based on poly(3-hexylthiophene) and Indene-C60 Bisadduct by Device Optimization", Advanced Materials, 2010, 9999, NA.

(8)    Y. J. He, G. J. Zhao, B. Peng, Y. F. Li, "High-Yield Synthesis and Electrochemical and Photovoltaic Properties of Indene-C-70 Bisadduct", Advanced Functional Materials, 2010, 20, 3383.

(9)    Xi Fan, Chaohua Cui, Guojia Fang, Jinzhao Wang, Songzhan Li, Fei Cheng, Hao Long, Yongfang Li, "Efficient Polymer Solar Cells Based on Poly(3-hexylthiophene):Indene-C70 Bisadduct with a MoO3 Buffer Layer", Advanced Functional Materials, 2012, 22, 585.

(10) Xiangyue Meng, Wenqing Zhang, Zhan'ao Tan, Chun Du, Cuihong Li, Zhishan Bo, Yongfang Li, Xiulin Yang, Mingming Zhen, Feng Jiang, Junpeng Zheng, Taishan Wang, Li Jiang, Chunying Shu, Chunru Wang, "Dihydronaphthyl-based [60]fullerene bisadducts for efficient and stable polymer solar cells", Chemical Communications, 2012, 48, 425.

(11)  Y. J. He, Y. F. Li, "Fullerene derivative acceptors for high performance polymer solar cells", Physical Chemistry Chemical Physics, 2011, 13, 1970.

(12)  Youjun He, Bo Peng, Guangjin Zhao, Yingping Zou, Yongfang Li, "Indene Addition of [6,6]-Phenyl-C61-butyric Acid Methyl Ester for High-Performance Acceptor in Polymer Solar Cells", the Journal of Physical Chemistry C, 2011, 115, 4340.

(13)  Youjun He, Hsiang-Yu Chen, Guangjin Zhao, Jianhui Hou, Yongfang Li, "Biindene-C60 adducts for the application as acceptor in polymer solar cells with higher open-circuit-voltage", Solar Energy Materials and Solar Cells, 2011, 95, 899.

(14)  Youjun He, Hsiang-Yu Chen, Guangjin Zhao, Jianhui Hou, Yongfang Li, "Synthesis and photovoltaic properties of biindene-C70 monoadduct as acceptor in polymer solar cells", Solar Energy Materials and Solar Cells, 2011, 95, 1762.

(15)  Yen-Ju Cheng, Chao-Hsiang Hsieh, Youjun He, Chain-Shu Hsu, Yongfang Li, "Combination of Indene-C60 Bis-Adduct and Cross-Linked Fullerene Interlayer Leading to Highly Efficient Inverted Polymer Solar Cells", Journal of the American Chemical Society, 2010, 132, 17381.

(16)  Petr P. Khlyabich, Beate Burkhart, Barry C. Thompson, "Efficient Ternary Blend Bulk Heterojunction Solar Cells with Tunable Open-Circuit Voltage", Journal of the American Chemical Society, 2011, 133, 14534.