Photoelectronic Porous Covalent Organic Materials: Research Progress and Perspective

doi:10.6023/A15020106

Abstract

Porous covalent organic materials (COM) are a class of multi-dimensional and multi-functional porous materials, which are built via covalent bond of colorful organic building blocks. COM materials possess inherent optimized pore size allowing ion migration, and high specific surface area, providing the possibility of formation of an electrostatic charge-separation layer, a conjugated system resulting in light-harvesting properties and a highly ordered structure, enabling the formation of conductive paths. In this review, we summary the applications on semiconductor, photolysis of water, solar cell, oxygen reduction reaction in fuel cell, lithium-ion/sulfur battery basing on COM materials. Meanwhile, we also propose the design strategy for photoelectronic materials. Although the development of COMs as photoelectronic materials is still in its infancy, COM materials has being attracting ever-increasing attention and open a new window in this field.

Key words: covalent organic frameworks, covalent organic polymers, semiconductor, photolysis of water, solar cell, oxygen reduction reaction, lithium ion battery, supercapacitor

Cite this article

Wan Gang, Fu Yu'ang, Guo Jianing, Xiang Zhonghua. Photoelectronic Porous Covalent Organic Materials: Research Progress and Perspective[J]. Acta Chim. Sinica, 2015, 73(6): 557-578.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Zhou, H.-C.; Long, J. R.; Yaghi, O. M. Chem. Rev. 2012, 112, 673.
[2] Furukawa, H.; Cordova, K. E.; O'Keeffe, M.; Yaghi, O. M. Science 2013, 341, 974.
[3] Xiang, Z. H.; Cao, D. P.; Lan, J. H.; Wang, W. C.; Broom, D. P. Energy Environ. Sci. 2010, 3, 1469.
[4] Xiang, Z. H.; Hu, Z.; Cao, D. P.; Yang, W. T.; Lu, J. M.; Han, B. Y.; Wang, W. C. Angew. Chem., Int. Ed. 2011, 50, 491.
[5] Xiang, Z. H.; Peng, X.; Cheng, X.; Li, X. J.; Cao, D. P. J. Phys. Chem. C 2011, 115, 19864.
[6] He, Y.; Tan, Y.; Zhang, J. Acta Chim. Sinica 2014, 72, 1228. (何燕萍, 谭衍曦, 张健, 化学学报, 2014, 72, 1228.)
[7] Liu, B.; Lian, Y.; Li, Z.; Chen, G. Acta Chim. Sinica 2014, 72, 942. (刘蓓, 廉源会, 李智, 陈光进, 化学学报, 2014, 72, 942.)
[8] Jia, J.; Wang, L.; Zhao, Q.; Sun, F.; Zhu, G. Acta Chim. Sinica 2013, 71, 1492. (贾江涛, 王蕾, 赵晴, 孙福兴, 朱广山, 化学学报, 2013, 71, 1492.)
[9] Zhu, W.-H.; Wang, Z.-M.; Gao, S. Inorg. Chem. 2007, 46, 1337.
[10] Li, W.; Gao, S.; Cheetham, A. K. Appl. Mater. 2014, 2, 123902.
[11] Xiang, Z. H.; Cao, D. P. J. Mater. Chem. A 2013, 1, 2691.
[12] Feng, X.; Ding, X.; Jiang, D. Chem. Soc. Rev. 2012, 41, 6010.
[13] Ding, S. Y.; Wang, W. Chem. Soc. Rev. 2013, 42, 548.
[14] Puthiaraj, P.; Pitchumani, K. Chem. Eur. J. 2014, 20, 8761.
[15] Zhao, Y.; Yao, K. X.; Teng, B.; Zhang, T.; Han, Y. Energy Environ. Sci. 2013, 6, 3684.
[16] McKeown, N. B.; Budd, P. M. Macromolecules 2010, 43, 5163.
[17] Ren, S.; Dawson, R.; Laybourn, A.; Jiang, J. X.; Khimyak, Y.; Adams, D. J.; Cooper, A. I. Polym. Chem. 2012, 3, 928.
[18] Xu, Y. H.; Jin, S. B.; Xu, H.; Nagai, A.; Jiang, D. L. Chem. Soc. Rev. 2013, 42, 8012.
[19] Cooper, A. I. Adv. Mater. 2009, 21, 1291.
[20] Vilela, F.; Zhang, K.; Antonietti, M. Energy Environ. Sci. 2012, 5, 7819.
[21] Cheng, G.; Bonillo, B.; Sprick, R. S.; Adams, D. J.; Hasell, T.; Cooper, A. I. Adv. Funct. Mater. 2014, 24, 5219.
[22] Zhang, T.; Wang, H.; Ma, H.; Sun, F.; Cui, X.; Zhu, G. Acta Chim. Sinica 2013, 71, 1598. (张婷婷, 王海涛, 马和平, 孙福兴, 崔小强, 朱广山, 化学学报, 2013, 71, 1598.)
[23] Jeon, H.-J.; Kim, D.-O.; Park, J.-S.; Kim, J.-S.; Kim, D.-W.; Jung, M.-S.; Shin, S.-W.; Lee, S.-W. Polymer-Korea 2011, 35, 66.
[24] Valderrama, C.; Gamisans, X.; Cortina, J. L.; Farran, A.; de Las Heras, F. X. J. Chem. Technol. Biotechnol. 2009, 84, 236.
[25] Yuan, D.; Lu, W.; Zhao, D.; Zhou, H.-C. Adv. Mater. 2011, 23, 3723.
[26] Lu, W. G.; Yuan, D. Q.; Sculley, J. L.; Zhao, D.; Krishna, R.; Zhou, H. C. J. Am. Chem. Soc. 2011, 133, 18126.
[27] Gao, X.; Lu, P.; Ma, Y. Chem. J. Chinese Univ. 2014, 35, 1795.
[28] Ben, T.; Qiu, S. CrystEngComm 2013, 15, 17.
[29] Ben, T.; Ren, H.; Ma, S.; Cao, D.; Lan, J.; Jing, X.; Wang, W.; Xu, J.; Deng, F.; Simmons, J. M.; Qiu, S.; Zhu, G. Angew. Chem., Int. Ed. 2009, 48, 9457.
[30] Wang, W.; Yan, Z.; Yuan, Y.; Sun, F.; Zhao, M.; Ren, H.; Zhu, G. Acta Chim. Sinica 2014, 72, 557. (王维, 闫卓君, 元野, 孙福兴, 赵明, 任浩, 朱广山, 化学学报, 2014, 72, 557.)
[31] Xiang, Z. H.; Cao, D. P. Macromol. Rapid Commun. 2012, 33, 1184.
[32] Xiang, Z. H.; Wang, W. C.; Cao, D. P. Sci. China Chem. 2012, 42, 235. (向中华, 汪文川, 曹达鹏, 中国科学化学, 2012, 42, 235.)
[33] Xiang, Z. H.; Cao, D. P.; Wang, W. C.; Yang, W. T.; Han, B. Y.; Lu, J. M. J. Phys. Chem. C 2012, 116, 5974.
[34] Xiang, Z. H.; Zhou, X.; Zhou, C. H.; Zhong, S.; He, X.; Qin, C. P.; Cao, D. P. J. Mater. Chem. 2012, 22, 22663.
[35] Xiang, Z. H.; Xue, Y. H.; Cao, D. P.; Huang, L.; Chen, J. F.; Dai, L. M. Angew. Chem. Int. Ed. 2014, 53, 2433.
[36] Xiang, Z. H.; Cao, D. P.; Huang, L.; Shui, J. L.; Wang, M.; Dai, L. M. Adv. Mater. 2014, 26, 3315.
[37] Dawson, R.; Cooper, A. I.; Adams, D. J. Prog. Polym. Sci. 2012, 37, 530.
[38] Zou, X.; Ren, H.; Zhu, G. Chem. Commun. 2013, 49, 3925.
[39] Bunz, U. H. F.; Seehafer, K.; Geyer, F. L.; Bender, M.; Braun, I.; Smarsly, E.; Freudenberg, J. Macromol. Rapid Commun. 2014, 35, 1466.
[40] Thomas, A. Angew. Chem., Int. Ed. 2010, 49, 8328.
[41] Zhu, G. S.; Ren, H. Porous Organic Frameworks: Design, Synthesis and Their Advanced Applications, Springer, 2014.
[42] Liu, X.-H.; Guan, C.-Z.; Wang, D.; Wan, L.-J. Adv. Mater. 2014, 26, 6912.
[43] Chang, Z.; Zhang, D. S.; Chen, Q.; Bu, X. H. Phys. Chem. Chem. Phys. 2013, 15, 5430.
[44] Dawson, R.; Cooper, A. I.; Adams, D. J. Polym. Int. 2013, 62, 345.
[45] Xu, H.; Chen, X.; Gao, J.; Lin, J.; Addicoat, M.; Irle, S.; Jiang, D. Chem. Commun. 2014, 50, 1292.
[46] Zhang, M.; Wang, X. Energy Environ. Sci. 2014, 7, 1902.
[47] Gu, C.; Huang, N.; Gao, J.; Xu, F.; Xu, Y. H.; Jiang, D. L. Angew. Chem., Int. Ed. 2014, 53, 4850.
[48] Altarawneh, S.; Nahar, L.; Arachchige, I. U.; Ala'a, O.; Hallal, K. M.; Kaafarani, B. R.; Rabbani, M. G.; Arvapally, R. K.; El-Kaderi, H. M. J. Mater. Chem. A 2015.
[49] Sang, N.; Zhan, C.; Cao, D. J. Mater. Chem. A 2015, 3, 92.
[50] Chen, L.; Honsho, Y.; Seki, S.; Jiang, D. J. Am. Chem. Soc. 2010, 132, 6742.
[51] Jiang, J.-X.; Trewin, A.; Adams, D. J.; Cooper, A. I. Chem. Sci. 2011, 2, 1777.
[52] Xu, Y.; Chen, L.; Guo, Z.; Nagai, A.; Jiang, D. J. Am. Chem. Soc. 2011, 133, 17622.
[53] Guo, J.; Xu, Y. H.; Jin, S. B.; Chen, L.; Kaji, T.; Honsho, Y.; Addicoat, M. A.; Kim, J.; Saeki, A.; Ihee, H.; Seki, S.; Irle, S.; Hiramoto, M.; Gao, J.; Jiang, D. L. Nat. Commun. 2013, 4, 2736.
[54] Dogru, M.; Bein, T. Chem. Commun. 2014, 50, 5531.
[55] Guo, B.; Ben, T.; Bi, Z.; Veith, G. M.; Sun, X.-G.; Qiu, S.; Dai, S. Chem. Commun. 2013, 49, 4905.
[56] Choi, N.-S.; Han, J.-G.; Ha, S.-Y.; Park, I.; Back, C.-K. RSC Adv. 2015, 5, 2732.
[57] Su, Y.; Liu, Y.; Liu, P.; Wu, D.; Zhuang, X.; Zhang, F.; Feng, X. Angew. Chem., Int. Ed. 2015, 54, 1812
[58] Filer, A.; Choi, H.-J.; Seo, J.-M.; Baek, J.-B. Phys. Chem. Chem. Phys. 2014, 16, 11150.
[59] Lino, M. A.; Lino, A. A.; Mazzoni, M. S. C. Chem. Phys. Lett. 2007, 449, 171.
[60] Huang, L.; Xiang, Z. H.; Cheng, D. J.; Lan, J. H.; Wang, W. C.; Ben, T.; Cao, D. P. Nanotechnology 2012, 23, 395702.
[61] Xiang, Z. H.; Cao, D. P.; Dai, L. M. Polym. Chem. 2015, 6, 1896.
[62] Phillip, W. A.; O'Neill, B.; Rodwogin, M.; Hillmyer, M. A.; Cussler, E. L. ACS Appl. Mater. Interfaces 2010, 2, 847.
[63] Kimmins, S. D.; Cameron, N. R. Adv. Funct. Mater. 2011, 21, 211.
[64] Patwardhan, S.; Kocherzhenko, A. A.; Grozema, F. C.; Siebbeles, L. D. A. J. Phys. Chem. C 2011, 115, 11768.
[65] Mei, J.; Diao, Y.; Appleton, A. L.; Fang, L.; Bao, Z. J. Am. Chem. Soc. 2013, 135, 6724.
[66] Côté, A. P.; Benin, A. I.; Ockwig, N. W.; O'Keeffe, M.; Matzger, A. J.; Yaghi, O. M. Science 2005, 310, 1166.
[67] Lukose, B.; Kuc, A.; Frenzel, J.; Heine, T. Beilstein J. Nanotechnol. 2010, 1, 60.
[68] Lukose, B.; Kuc, A.; Heine, T. Chem. Eur. J. 2011, 17, 2388.
[69] Koo, B. T.; Dichtel, W. R.; Clancy, P. J. Mater. Chem. 2012, 22, 17460.
[70] Medina, D. D.; Werner, V.; Auras, F.; Tautz, R.; Dogru, M.; Schuster, J.; Linke, S.; Doeblinger, M.; Feldmann, J.; Knochel, P.; Bein, T. ACS Nano 2014, 8, 4042.
[71] Colson, J. W.; Woll, A. R.; Mukherjee, A.; Levendorf, M. P.; Spitler, E. L.; Shields, V. B.; Spencer, M. G.; Park, J.; Dichtel, W. R. Science 2011, 332, 228.
[72] Xu, L.; Zhou, X.; Tian, W. Q.; Gao, T.; Zhang, Y. F.; Lei, S.; Liu, Z. F. Angew. Chem., Int. Ed. 2014, 53, 9564.
[73] Gunasinghe, R. N.; Reuven, D. G.; Suggs, K.; Wang, X.-Q. J. Phys. Chem. Lett. 2012, 3(20), 3048.
[74] Wan, S.; Guo, J.; Kim, J.; Ihee, H.; Jiang, D. Angew. Chem., Int. Ed. 2008, 120, 8958.
[75] Wan, S.; Guo, J.; Kim, J.; Ihee, H.; Jiang, D. Angew. Chem., Int. Ed. 2009, 48, 5439.
[76] Feng, X.; Chen, L.; Honsho, Y.; Saengsawang, O.; Liu, L.; Wang, L.; Saeki, A.; Irle, S.; Seki, S.; Dong, Y.; Jiang, D. Adv. Mater. 2012, 24, 3026.
[77] Spitler, E. L.; Dichtel, W. R. Nat. Chem. 2010, 2(8), 672.
[78] Ding, X.; Guo, J.; Feng, X.; Honsho, Y.; Guo, J.; Seki, S.; Maitarad, P.; Saeki, A.; Nagase, S.; Jiang, D. Angew. Chem., Int. Ed. 2011, 50, 1289.
[79] Ding, X.; Chen, L.; Honsho, Y.; Feng, X.; Saenpawang, O.; Guo, J.; Saeki, A.; Seki, S.; Irle, S.; Nagase, S.; Parasuk, V.; Jiang, D. J. Am. Chem. Soc. 2011, 133, 14510.
[80] Jin, S. B; Ding, X. H; Feng, X.; Super, M.; Furukawa, K.; Takahashi, S.; Addicoat, M.; El-Khouly, M. E.; Nakamura, T.; Irle, S. Angew. Chem., Int. Ed. 2013, 52(7), 2017.
[81] Gandara, Y.; Asano, A.; Furukawa, H.; Sasaki, A.; Dey, S. K.; Liao, L.; Ambrogio, M. W.; Botros, Y. Y.; Duan, X. F.; Seki, S.; Stoddart, J. F.; Yaghi, O. M. Chem. Mater. 2011, 23(18), 4094
[82] Feng, X.; Liu, L.; Honsho, Y.; Saeki, A.; Seki, S.; Irle, S.; Dong, Y.; Nagai, A.; Jiang, D. Angew. Chem., Int. Ed. 2012, 51, 2618.
[83] Bertrand, G. H.; Michaelis, V. K.; Ong, T.-C.; Griffin, R. G.; Dinc?, M. Proc. Natl. Acad. Sci. 2013, 110, 4923.
[84] Dogru, M.; Handloser, M.; Auras, F.; Kunz, T.; Medina, D.; Hartschuh, A.; Knochel, P.; Bein, T. Angew. Chem., Int. Ed. 2013, 52, 2920.
[85] Linsebigler, A. L.; Lu, G.; Yates Jr, J. T. Chem. Rev. 1995, 95, 735.
[86] Kudo, A.; Miseki, Y. Chem. Soc. Rev. 2009, 38, 253.
[87] Groenewolt, M.; Antonietti, M. Adv. Mater. 2005, 17, 1789.
[88] Wang, X.; Maeda, K.; Thomas, A.; Takanabe, K.; Xin, G.; Carlsson, J. M.; Domen, K.; Antonietti, M. Nat. Mater. 2008, 8, 76.
[89] Wang, X.; Maeda, K.; Chen, X.; Takanabe, K.; Domen, K.; Hou, Y.; Fu, X.; Antonietti, M. J. Am. Chem. Soc. 2009, 131, 1680.
[90] Li, Q.; Yue, B.; Iwai, H.; Kako, T.; Ye, J. J. Phys. Chem. C 2010, 114, 4100.
[91] Stegbauer, L.; Schwinghammer, K.; Lotsch, B. V. Chem. Sci. 2014, 5, 2789.
[92] Habas, S. E.; Platt, H. A.; van Hest, M. F.; Ginley, D. S. Chem. Rev. 2010, 110, 6571.
[93] Hoppe, H.; Sariciftci, N. S. J. Mater. Res. 2004, 19, 1924.
[94] Joshi, D.; Shivanna, R.; Narayan, K. S. J. Mod. Optic. 2014, 61, 1703.
[95] Chang, J. A.; Rhee, J. H.; Im, S. H.; Lee, Y. H.; Kim, H.-J.; Seok, S. I.; Nazeeruddin, M. K.; Gratzel, M. Nano Lett. 2010, 10, 2609.
[96] Heo, J. H.; Im, S. H.; Noh, J. H.; Mandal, T. N.; Lim, C.-S.; Chang, J. A.; Lee, Y. H.; Kim, H.-J.; Sarkar, A.; Nazeeruddin, M. K.; Graetzel, M.; Seok, S. I. Nat. Photonics 2013, 7, 487.
[97] O’Regan,B.; Gratzel, M. Nature 1991,353,737.
[98] Chen, L.; Furukawa, K.; Gao, J.; Nagai, A.; Nakamura, T.; Dong, Y.; Jiang, D. J. Am. Chem. Soc. 2014, 136, 9806.
[99] Gasteiger, H. A.; Kocha, S. S.; Sompalli, B.; Wagner, F. T. Appl. Catal. B-Environ. 2005, 56, 9.
[100] Feng, Y. J.; Alonso-Vante, N. Phys. Status Solidi B 2008, 245, 1792.
[101] Zhao, H.; Jin, Z.; Su, H.; Jing, X.; Sun, F.; Zhu, G. Chem. Commun. 2011, 47, 6389.
[102] Pachfule, P.; Dhavale, V. M.; Kandambeth, S.; Kurungot, S.; Banerjee, R. Chem. Eur. J. 2013, 19, 974.
[103] Wu, Z. S.; Chen, L.; Liu, J. Z.; Parvez, K.; Liang, H. W.; Shu, J.; Sachdev, H.; Graf, R.; Feng, X. L.; Mullen, K. Adv. Mater. 2014, 26, 1450.
[104] Zhuang, X.; Zhang, F.; Wu, D.; Forler, N.; Liang, H.; Wagner, M.; Gehrig, D.; Hansen, M. R.; Laquai, F.; Feng, X. Angew. Chem., Int. Ed. 2013, 52, 9668.
[105] Zhang, Y.; Zhuang, X.; Su, Y.; Zhang, F.; Feng, X. J. Mater. Chem. A 2014, 21(2), 7742.
[106] Song, Z.; Zhou, H. Energy Environ. Sci. 2013, 6, 2280.
[107] Xu, F.; Chen, X.; Tang, Z.; Wu, D.; Fu, R.; Jiang, D. Chem. Commun. 2014, 50, 4788.
[108] Huang, Y.; Wu, D.; Wang, J.; Han, S.; Lv, L.; Zhang, F.; Feng, X. Small 2014, 10, 2226.
[109] Kwon, M.-S.; Choi, A.; Park, Y.; Cheon, J. Y.; Kang, H.; Jo, Y. N.; Kim, Y.-J.; Hong, S. Y.; Joo, S. H.; Yang, C.; Lee, K. T. Sci. Rep. 2014, 4, 7404.
[110] Poizot, P.; Laruelle, S.; Grugeon, S.; Dupont, L.; Tarascon, J. Nature 2000, 407, 496.
[111] Bruce, P. G.; Scrosati, B.; Tarascon, J.-M. Angew. Chem., Int. Ed. 2008, 47, 2930.
[112] Xiao, L.; Cao, Y.; Xiao, J.; Schwenzer, B.; Engelhard, M. H.; Saraf, L. V.; Nie, Z.; Exarhos, G. J.; Liu, J. Adv. Mater. 2012, 24, 1176.
[113] Tarascon, J. M.; Armand, M. Nature 2001, 414, 359.
[114] Goodenough, J. B.; Kim, Y. Chem. Mater. 2010, 22, 587.
[115] Liao, H.; Ding, H.; Li, B.; Ai, X.; Wang, C. J. Mater. Chem. A 2014, 2, 8854.
[116] Winter, M.; Brodd, R. J. Chem. Rev. 2004, 104, 4245.
[117] Feng, X.; Liang, Y.; Zhi, L.; Thomas, A.; Wu, D.; Lieberwirth, I.; Kolb, U.; Müllen, K. Adv. Funct. Mater. 2009, 19, 2125.
[118] Liang, Y.; Feng, X.; Zhi, L.; Kolb, U.; Müllen, K. Chem. Commun. 2009, 809.
[119] Bao, Q.; Bao, S.; Li, C. M.; Qi, X.; Pan, C.; Zang, J.; Lu, Z.; Li, Y.; Tang, D. Y.; Zhang, S. J. Phys. Chem. C 2008, 112, 3612.
[120] Béguin, F.; Szostak, K.; Lota, G.; Frackowiak, E. Adv. Mater. 2005, 17, 2380.
[121] Raymundo-Piñero, E.; Leroux, F.; Béguin, F. Adv. Mater. 2006, 18, 1877.
[122] Xiang, Z. H.; Wang, D.; Xue, Y. H.; Dai, L. M.; Chen, J. F.; Cao, D. P. Sci. Rep. 2015, 5, 8307.
[123] Li, Y.; Roy, S.; Ben, T.; Xua, S.; Qiu, S. Phys. Chem. Chem. Phys. 2014, 16, 12909.
[124] Liu, X.; Zhou, L.; Zhao, Y.; Bian, L.; Feng, X.; Pu, Q. ACS Appl. Mater. Interfaces 2013, 5, 10280.
[125] Zhuang, X.; Zhang, F.; Wu, D.; Feng, X. Adv. Mater. 2014, 26, 3081.
[126] Yang, X.; Zhuang, X.; Huang, Y.; Jiang, J.; Tian, H.; Wu, D.; Zhang, F.; Mai, Y.; Feng, X. Polym. Chem. 2015, 6, 1088.
[127] Kou, Y.; Xu, Y.; Guo, Z.; Jiang, D. Angew. Chem., Int. Ed. 2011, 50, 8753.
[128] Yamada, H.; Nakamura, H.; Nakahara, F.; Moriguchi, I.; Kudo, T. J. Phys. Chem. C 2007, 111, 227.

光电多孔共价有机材料的研究进展 2017 Awarded