中文
Earlier issues
Announcement
More
Progress in Chemistry 2015, Vol. 27 Issue (6): 641-654 DOI: 10.7536/PC141211 Previous Articles   Next Articles

• Supramolecular Chemistry Issue •

Recent Development of Constructing Porphyrin Arrays via Suzuki-Miyaura Cross-Coupling Reaction

Chen Maolong, Yin Bangshao, Song Jianxin*   

  1. Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Key Laboratory of the Assembly and Application of Organic Functional Molecules, Hunan Normal University, Changsha 410081, China
  • Received: Revised: Online: Published:
  • Contact: 10.7536/PC141211 E-mail:jxsong@hunnu.edu.cn
  • Supported by:
    The work was supported by the National Natural Science Foundation of China (No. 21272065), the Scientific Research Foundation for the Returned Overseas Chinese Scholars, the Scientific Research Fund of Hunan Provincial Educational Department (No. 13k027), the Aid Program for Science and Technology Innovative Research Team in Higher Educational Institutions of Hunan Province, and the Construct Program of the Key Discipline in Hunan Province.
PDF ( 1438 ) Cited
Export

EndNote

Ris

BibTeX

Porphyrin arrays are multiporphyrinic systems which assembled either by bridging units or bonds. The electronic properties of porphyrin arrays depend on the bridging units and the bridging positions on porphyrins. In the last two decades, electronically interacting multiporphyrinic systems have been actively explored due to their potential applications in optoelectronic devices, sensors, photovoltaic devices, nonlinear optical materials, and photodynamic therapy pigments. Porphyrin arrays can be constructed by means of noncovalent bonds or covalent bonds, the former is easy but the assembled array is unstable while the latter is opposite. The Suzuki-Miyaura coupling reaction is classified as a coupling reaction where the coupling partners are a boronic acid or borate ester with a halide catalyzed by a palladium (0) complex. It is an efficient method to construct porphyrin arrays with diversity structures and different properties. In this review, the emphasis has been placed upon the progress in the construction of the porphyrin arrays via Suzuki-Miyaura reaction. At last, we prospect the development trend of constructing porphyrin arrays via Suzuki-Miyaura coupling reaction.

Contents
1 Introduction
2 meso-meso bridged porphyrin arrays
3 meso-β bridged porphyrin arrays
4 β-β bridged porphyrin arrays
5 Conclusion and outlook

Key words: construction, porphyrin arrays, Suzuki-Miyaura coupling reaction

CLC Number: 

[1] Tanaka T, Osuka A. Chem. Soc. Rev., 2015, 44: 943.
[2] Li W S, Aida T. Chem. Rev., 2009, 109: 6047.
[3] (a) Cuesta L, Sessler J L. Chem. Soc. Rev., 2009, 38: 2716.; (b) Faiz J A, Heitz V, Sauvage J P. Chem. Soc. Rev., 2009, 38: 422.; (c) Gao W Y, Chrzanowski M, Ma S. Chem. Soc. Rev., 2014, 43: 5841.
[4] Ethirajan M, Chen Y, Joshi P, Pandey R K. Chem. Soc. Rev., 2011, 40: 340.
[5] Li L L, Diau E W. Chem. Soc. Rev., 2013, 42: 291.
[6] (a) D'Souza F, Subbaiyan N K, Xie Y, Hill J P, Ariga K, Ohkubo K, Fukuzumi S. J. Am. Chem. Soc., 2009, 131: 16138.; (b) Xie Y, Hill J P, Schumacher A L, Sandanayaka A S D, Araki Y, Karr P A, Labuta J, D'Souza F, Ito O, Anson C E, Powell A K, Ariga K. J. Phys. Chem. C, 2008, 112: 10559.
[7] (a) Urbani M, Michael Grätzel M, Nazeeruddin M K, Torres T. Chem. Rev., 2014, 114: 12330.; (b) Wang Y, Chen B, Wu W, Li X, Zhu W, Tian H, Xie Y. Angew. Chem. Int. Ed., 2014, 53: 10779.; (c) Sun X, Wang Y, Li X, Ögren H, Zhu W, Tian H, Xie Y. Chem. Commun., 2014, 50: 15609.
[8] Beletskaya I P, Ananikov V P. Chem. Rev., 2011, 111: 1596.
[9] Jana R, Pathak T P, Sigman M S. Chem. Rev., 2011, 111: 1417.
[10] Liu C, Zhang H, Shi W, Lei A. Chem. Rev., 2011, 111: 1780.
[11] Roglans A, Pla-Quintana A, Moreno-Maas M. Chem. Rev., 2006, 106: 4622.
[12] Han F S. Chem. Soc. Rev., 2013, 42: 5270.
[13] Miyaura N, Yamada K, Suzuki A. Tetrahedron Lett., 1979, 20: 3437.
[14] Miyaura N, Suzuki A. Chem. Commun., 1979: 866.
[15] Miyaura N, Suzuki A. Chem. Rev., 1995, 95: 2457.
[16] Nobelprize.org In Nobel Prize Foundation . http://www.nobelprize.org/nobel_prizes/chemistry/laureates/2010/, 2010.
[17] Kurotobi K, Osuka A. Org. Lett., 2005, 7: 1055.
[18] Li B, Li J, Fu Y, Bo Z. J. Am. Chem. Soc., 2004, 126: 3430.
[19] Barker C A, Zeng X, Bettington S, Batsanov A S, Bryce M R, Beeby A. Chem. A Eur. J, 2007, 13: 6710.
[20] Yamaguchi S, Katoh T, Shinokubo H, Osuka A. J. Am. Chem. Soc., 2007, 129: 6392.
[21] Yamaguchi S, Katoh T, Shinokubo H, Osuka A. J. Am. Chem. Soc., 2008, 130: 14440.
[22] Agarwal N. Dyes and Pigments, 2009, 83: 328.
[23] Ali H, Ait-Mohand S, Gosselin S, van Lier J E, Guerin B. J. Org. Chem., 2011, 76: 1887.
[24] Arnold L, Baumgarten M, Mullen K. Chem. Commun., 2012, 48: 9640.
[25] Michalak J, Birin K P, Muniappan S, Ranyuk E, Enakieva Y Y, Gorbunova Y G, Stern C, Bessmertnykh-Lemeune A, Guilard R. J. Porphyrins Phthalocyanines, 2014, 18: 35.
[36] Hwang I W, Kamada T, Ahn T K, Ko D M, Nakamura T, Tsuda A, Osuka A, Kim D. J. Am. Chem. Soc., 2004, 126: 16187.
[27] Mori S, Kim K S, Yoon Z S, Noh S B, Kim D, Osuka A. J. Am. Chem. Soc., 2007, 129: 11344.
[28] Tsurumaki E, Inokuma Y, Easwaramoorthi S, Lim J M, Kim D, Osuka A. Chem. Eur. J., 2009, 15: 237.
[29] Hayashi S Y, Inokuma Y, Osuka A. Org. Lett., 2010, 12: 4148.
[30] Kitano M, Hayashi S Y, Tanaka T, Yorimitsu H, Aratani N, Osuka A. Angew. Chem. Int. Ed., 2012, 51: 5593.
[31] Berg S, Thomas K F, Beavers C M, Ghosh A. Inorg. Chem., 2012, 51: 9911.
[32] Aratani N, Cho H S, Ahn T K, Cho S, Kim D, Sumi H, Osuka A. J. Am. Chem. Soc., 2003, 125: 9668.
[33] Tsuda A, Osuka A. Science, 2001, 293: 79.
[34] Aratani N, Takagi A, Yanagawa Y, Matsumoto T, Kawai T, Yoon Z S, Kim D, Osuka A. Chem. Eur. J., 2005, 11: 3389.
[35] Peng X, Komatsu N, Kimura T, Osuka A. J. Am. Chem. Soc., 2007, 129: 15947.
[36] Kozaki M, Uetomo A, Suzuki S, Okada K. Org. Lett., 2008, 10: 4477.
[37] Aratani N, Osuka A. Chem. Commun., 2008, 4067.
[38] Maeda C, Shinokubo H, Osuka A. Org. Lett., 2010, 12: 1820.
[39] Song J, Aratani N, Shinokubo H, Osuka A. Chem. Eur. J., 2010, 16: 13320.
[40] Osawa K, Song J, Furukawa K, Shinokubo H, Aratani N, Osuka A. Chem. Asian J., 2010, 5: 764.
[41] Jiang H W, Ham S, Aratani N, Kim D, Osuka A. Chem. Eur. J., 2013, 19: 13328.
[42] Tamaki T, Nosaka T, Ogawa T. J. Org. Chem., 2014, 79: 11029.
[43] Hiroto S, Hisaki I, Shinokubo H, Osuka A. Angew. Chem. Int. Ed., 2005, 44: 6763.
[44] Hata H, Shinokubo H, Osuka A. J. Am. Chem. Soc., 2005, 127: 8264.
[45] Ikeda T, Aratani N, Easwaramoorthi S, Kim D, Osuka A. Org. Lett., 2009, 11: 3080.
[46] Heo J H, Ikeda T, Lim J M, Aratani N, Osuka A, Kim D. J. Phys. Chem. B, 2010, 114: 14528.
[47] Song J, Aratani N, Kim P, Kim D, Shinokubo H, Osuka A. Angew. Chem. Int. Ed., 2010, 49: 3617.
[48] Song J, Anabuki S, Aratani N, Shinokubo H, Osuka A. Chem. Lett., 2011, 40: 902.
[49] Bringmann G, Goetz D C G, Gulder T A M, Gehrke T H, Bruhn T, Kupfer T, Radacki K, Braunschweig H, Heckmann A, Lambertt C. J. Am. Chem. Soc., 2008, 130: 17812.
[50] Song J, Jang S Y, Yamaguchi S, Sankar J, Hiroto S, Aratani N, Shin J Y, Easwaramoorthi S, Kim K S, Kim D, Shinokubo H, Osuka A. Angew. Chem. Int. Ed., 2008, 47: 6004.
[51] Song J, Aratani N, Shinokubo H, Osuka A. Chem. Sci., 2011, 2: 748.
[52] Song J, Kim P, Aratani N, Kim D, Shinokubo H, Osuka A. Chem. Eur. J., 2010, 16: 3009.
[53] Song J, Aratani N, Heo J H, Kim D, Shinokubo H, Osuka A. J. Am. Chem. Soc., 2010, 132: 11868.
[54] Song J, Aratani N, Shinokubo H, Osuka A. J. Am. Chem. Soc., 2010, 132: 16356.
[55] Cunha A C, Gomes A T P C, Ferreira V F, de Souza M C B V, Neves M G P M S, Tome A C, Silva A M S, Cavaleiro J A S. Synthesis, 2010: 510.
[56] Ikeda S, Aratani N, Osuka A. Chem. Commun., 2012, 48: 4317.
[57] Hao Q, Zeng Y, Yu T, Chen J, Yang G, Li Y. Chem. Asian J., 2013, 8: 1015.
[58] Cai H, Fujimoto K, Lim J M, Wang C, Huang W, Rao Y, Zhang S, Shi H, Yin B, Chen B, Ma M, Song J, Kim D, Osuka A. Angew. Chem. Int. Ed., 2014, 53: 11088.
[1] Wenfu Yan, Ruren Xu. Chemical Reactions in Aqueous Solutions with Condensed Liquid State* [J]. Progress in Chemistry, 2022, 34(7): 1454-1491.
[2] Xueer Cai, Meiling Jian, Shaohong Zhou, Zefeng Wang, Kemin Wang, Jianbo Liu. Chemical Construction of Artificial Cells and Their Biomedical Applications [J]. Progress in Chemistry, 2022, 34(11): 2462-2475.
[3] Yifeng Chen, Cong Wang, Kefeng Ren, Jian Ji. Droplet Microarrays in Biomedical High-Throughput Research [J]. Progress in Chemistry, 2021, 33(4): 543-554.
[4] Ruren Xu, Jihong Yu, Wenfu Yan. Goals and Major Scientific Issues in Condensed Matter Chemistry [J]. Progress in Chemistry, 2020, 32(8): 1017-1048.
[5] Na Li, Ze Chang, Qiang Chen, Jiacheng Yin, Xian-He Bu. Construction and Modulation of Dynamic Coordination Space [J]. Progress in Chemistry, 2019, 31(1): 10-20.
[6] Zhang Teng, Peng Yunhui, Tong Huimin, Matthew J Rames, Zhang Lei, Ren Gang*. IPET: An Experimental Method to Determine the 3-Dimensional Structure of An Individual Macromolecule [J]. Progress in Chemistry, 2013, 25(05): 669-676.
[7] Liu Bing,Chen Haitao,Qian Dongjin**. Interfacial Assembly of Metal-Mediated Multiporphyrin Arrays and Nanocrystals [J]. Progress in Chemistry, 2007, 19(06): 872-877.