Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
Shopping Cart: ( empty )
You are here: Home > Journals > CH > CH14562
RESEARCH ARTICLE
Contents Vol 68(7)

Synthesis, Structural Characterisation, and Spectroscopic Properties of Copper(i) Complexes and their Applications to Dye-Sensitised Solar Cells

Ting-Hong Huang A C , Jie Yan A , Ye-Feng Liu A , Yun-Tao Xie A and Chen Jia B
+ Author Affiliations
- Author Affiliations

A Key Laboratories of Fine Chemicals and Surfactants in Sichuan Provincial Universities, Material Corrosion and Protection Key Laboratory of Sichuan Province, College of Materials and Chemical Engineering, Sichuan University of Science & Engineering, Zigong 643000, China.

B Key Laboratory of Chemistry of Northwestern Plant Resources, Key Laboratory for Natural Med icine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China.

C Corresponding author. Email: hth_chem@126.com

Australian Journal of Chemistry 68(7) 1144-1151 https://doi.org/10.1071/CH14562
Submitted: 13 September 2014  Accepted: 8 December 2014   Published: 2 March 2015

Abstract

Based on the ligand 1,4-bis(2-(diphenylphophino)benzylideneamino)benzene (pbb), two complexes, [Cu2(pbb)(2,2′-bipyridine)2](BF4)2 (1) and [Cu2(pbb)(phen)2](BF4)2 (2), have been prepared and characterised by IR, 1H NMR, 31P NMR, 19F NMR, and 11B NMR spectroscopy and X-ray crystal structure analysis. Structural analysis reveals that complexes 1 and 2 contain 1D infinite chains and 2D supramolecular networks constructed by C–H···π and π···π interactions, and an ordered-layer-lattice of BF4– is located between these 2D networks. The results show that C–H···π and π···π interactions play an important role in the formation of 2D supramolecular networks. The UV-vis absorption peaks of complexes 1 and 2 display intraligand charge transfer and metal to ligand charge transfer (MLCT) absorption. Complexes 1 and 2 display efficient luminescent emission assigned to MLCT excited states, and the maximum emissions of these complexes in acetonitrile solution are different from those of the solid-state samples. In addition, complexes 1 and 2 have been exploited as sensitisers in dye-sensitised solar cells, and efficiencies are also observed.


References

[1]  A. M. Bunzli, H. J. Bolink, E. C. Constable, C. E. Housecroft, J. M. Junquera-Hernandez, M. Neuburger, E. Orti, A. Pertegas, J. J. Serrano-Perez, D. Tordera, J. A. Zampese, Dalton Trans. 2014, 43, 738.
         | Crossref | GoogleScholarGoogle Scholar | 24145467PubMed |

[2]  H.-F. Chen, W.-Y. Hung, S.-W. Chen, T.-C. Wang, S.-W. Lin, S.-H. Chou, C.-T. Liao, H.-C. Su, H.-A. Pan, P.-T. Chou, Y.-H. Liu, K.-T. Wong, Inorg. Chem. 2012, 51, 12114.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhsFOltrbF&md5=ca193cf5f9abaced251f65af3990a95cCAS | 23102402PubMed |

[3]  R. D. Costa, F. J. Cespedes-Guirao, E. Orti, H. J. Bolink, J. Gierschner, F. Fernandez-Lazaro, A. Sastre-Santos, Chem. Commun. 2009, 3886.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXns1Slurc%3D&md5=947ec6b2d05ba1246ccaa72ce5ed8efeCAS |

[4]  K. Hasan, L. Donato, Y. Shen, J. D. Slinker, E. Zysman-Colman, Dalton Trans. 2014, 43, 13672.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXht1aiur%2FM&md5=70738e6f2405673fce4d641690e70d47CAS | 25098328PubMed |

[5]  G. E. Schneider, A. Pertegas, E. C. Constable, C. E. Housecroft, N. Hostettler, C. D. Morris, J. A. Zampese, H. J. Bolink, J. M. Junquera-Hernandez, E. Orti, M. Sessolo, J. Mater. Chem. C 2014, 2, 7047.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhtFehsbnM&md5=e64a9da1db25a2c6e5c8efd8294b0204CAS |

[6]  D. Tordera, A. M. Bünzli, A. Pertegás, J. M. Junquera-Hernández, E. C. Constable, J. A. Zampese, C. E. Housecroft, E. Ortí, H. J. Bolink, Chem. – Eur. J. 2013, 19, 8597.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXntF2mtbw%3D&md5=9ee2f9a63672973cf54f2106197cc3a4CAS | 23649547PubMed |

[7]  K. B. Aribia, T. Moehl, S. M. Zakeeruddin, M. Gratzel, Chem. Sci. 2013, 4, 454.
         | Crossref | GoogleScholarGoogle Scholar |

[8]  E. C.-H. Kwok, M.-Y. Chan, K. M.-C. Wong, V. W.-W. Yam, Chem. – Eur. J. 2014, 20, 3142.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXisFSns7g%3D&md5=fe708e958262c4546ac19b165188e6e6CAS |

[9]  Q. Miao, S. Zhang, H. Xu, P. Zhang, H. Li, Chem. Commun. 2013, 49, 6980.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtVOjsL7P&md5=679e787f753b02c32eb27ca157ccc33eCAS |

[10]  J.-S. Ni, K.-C. Ho, K.-F. Lin, J. Mater. Chem. A. 2013, 1, 3463.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXisVGju7w%3D&md5=053481a4a3ea937f329b478dbe255baeCAS |

[11]  S. H. Wadman, J. M. Kroon, K. Bakker, R. W. A. Havenith, G. P. M. van Klink, G. van Koten, Organometallics 2010, 29, 1569.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXislKitLw%3D&md5=d47e9eb7531045ee1daf6b9dd00ba30aCAS |

[12]  J. Xu, H. Wu, X. Jia, D. Zou, Chem. Commun. 2012, 48, 7793.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhtVSlsb3J&md5=836b4454f7c77c848c40e666d4522361CAS |

[13]  M. He, Z. Ji, Z. Huang, Y. Wu, J. Phys. Chem. C 2014, 118, 16518.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXisFahsb8%3D&md5=15c60bc6c63aa6dbbf18da47dd0fdcacCAS |

[14]  T. Hewat, S. McDonald, J. Lee, M. Rahman, P. Cameron, F.-C. Hu, Y. Chi, L. J. Yellowlees, N. Robertson, RSC Adv. 2014, 4, 10165.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXisVWlsbg%3D&md5=b9c0e18354a8abe5da228beef8c16bf6CAS |

[15]  C.-W. Hsu, S.-T. Ho, K.-L. Wu, Y. Chi, S.-H. Liu, P.-T. Chou, Energy Environ. Sci. 2012, 5, 7549.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xnslagu74%3D&md5=5a90c2ff223cff238519ab9f5cdf31ffCAS |

[16]  M. Hussain, A. Islam, I. Bedja, R. K. Gupta, L. Han, A. El-Shafei, Phys. Chem. Chem. Phys. 2014, 16, 14874.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhtVKgs7vE&md5=213a2dfb0f52e3894d8ea8dcb6fbb039CAS | 24926746PubMed |

[17]  G. C. Vougioukalakis, T. Stergiopoulos, A. G. Kontos, E. K. Pefkianakis, K. Papadopoulos, P. Falaras, Dalton Trans. 2013, 42, 6582.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXnsVChsLw%3D&md5=e25d1b0c7117fc237ec45dd2abae5c47CAS | 23474693PubMed |

[18]  K. A. Wills, H. J. Mandujano-Ramirez, G. Merino, D. Mattia, T. Hewat, N. Robertson, G. Oskam, M. D. Jones, S. E. Lewis, P. J. Cameron, RSC Adv. 2013, 3, 23361.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhs1ylt7zJ&md5=12821808e8f40ed994d2eb2ae39da673CAS |

[19]  T. Bessho, E. C. Constable, M. Graetzel, A. Hernandez Redondo, C. E. Housecroft, W. Kylberg, M. K. Nazeeruddin, M. Neuburger, S. Schaffner, Chem. Commun. 2008, 3717.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXpsVOhsrc%3D&md5=013d5000581c25a39d9d9d7d3e8835d4CAS |

[20]  E. C. Constable, A. H. Redondo, C. E. Housecroft, M. Neuburger, S. Schaffner, Dalton Trans. 2009, 6634.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXps1Klsr4%3D&md5=b367b413a6f040e21b9f01a329095dc3CAS | 19672508PubMed |

[21]  M. Sandroni, M. Kayanuma, A. Planchat, N. Szuwarski, E. Blart, Y. Pellegrin, C. Daniel, M. Boujtita, F. Odobel, Dalton Trans. 2013, 42, 10818.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtVOku7nL&md5=a6d92f4c90b63bbfcc74d8edae9390daCAS | 23783812PubMed |

[22]  B. Bozic-Weber, E. C. Constable, S. O. Furer, C. E. Housecroft, L. J. Troxler, J. A. Zampese, Chem. Commun. 2013, 49, 7222.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtFaltbrO&md5=7ac0604cc66a94b46ec7393220d9390cCAS |

[23]  J. Baldenebro-Lopez, N. Flores-Holguin, J. Castorena-Gonzalez, D. Glossman-Mitnik, J. Photochem. Photobiol. A. 2013, 267, 1.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXht1SjurnN&md5=d24403d9cd0b25e07be07aa248816e48CAS |

[24]  D. G. Cuttell, S.-M. Kuang, P. E. Fanwick, D. R. McMillin, R. A. Walton, J. Am. Chem. Soc. 2002, 124, 6.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXovV2gtbw%3D&md5=4361aad68bdf22e16cd542e66ecf862aCAS | 11772046PubMed |

[25]  R. Hou, T.-H. Huang, X.-J. Wang, X.-F. Jiang, Q.-L. Ni, L.-C. Gui, Y.-J. Fan, Y.-L. Tan, Dalton Trans. 2011, 40, 7551.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXos1GltLs%3D&md5=22ab38fe090e71b7feb27e0d497b921aCAS | 21706081PubMed |

[26]  B. Bozic-Weber, S. Y. Brauchli, E. C. Constable, S. O. Furer, C. E. Housecroft, I. A. Wright, Phys. Chem. Chem. Phys. 2013, 15, 4500.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXjsFGksro%3D&md5=529b6c1fd377e54a81793e32cf0b0fd5CAS | 23440045PubMed |

[27]  A. J. Blake, N. R. Champness, A. N. Khlobystov, D. A. Lemenovskii, W.-S. Li, M. Schroder, Chem. Commun. 1997, 1339.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXltlSjtrc%3D&md5=5afdd9276b121edcfcaae35127b2056cCAS |

[28]  P. O. Oguadinma, F. Schaper, Organometallics 2009, 28, 6721.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtleksLbO&md5=2bdf021894fc95bf2a9fb57b4a98e784CAS |

[29]  D. L. Reger, A. Debreczeni, B. Reinecke, V. Rassolov, M. D. Smith, R. F. Semeniuc, Inorg. Chem. 2009, 48, 8911.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtVens7jK&md5=ed31fe73dfe2277374c5ef03dde37e91CAS | 19697953PubMed |

[30]  K.-i. Sakai, T. Akutagawa, T. Hasegawa, T. Nakamura, Phys. Chem. Chem. Phys. 2003, 5, 2469.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXjvVahsbY%3D&md5=f2b6d3bc1082cb0d2bb3f0b31cff25e1CAS |

[31]  M. Sandroni, L. Favereau, A. Planchat, H. Akdas-Kilig, N. Szuwarski, Y. Pellegrin, E. Blart, H. Le Bozec, M. Boujtita, F. Odobel, J. Mater. Chem. A 2014, 2, 9944.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhtVWmu7jL&md5=ae431fbfff5eacc71f049fecf7d44ea4CAS |

[32]  H. Hofmeier, U. S. Schubert, Chem. Soc. Rev. 2004, 33, 373.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXmtVWgurw%3D&md5=138a8e8ef1c3b87eef1fab8fef90cbc8CAS | 15280970PubMed |

[33]  M. Adams, C. de Kock, P. J. Smith, K. Chibale, G. S. Smith, J. Organomet. Chem. 2013, 736, 19.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXmvV2ku7o%3D&md5=cecc72ba6ddcb06a4eec6efd11869399CAS |

[34]  T. B. Rauchfuss, J. Organomet. Chem. 1978, 162, C19.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE1MXnt1eitg%3D%3D&md5=78ae066a7ffee456723dcbb906e8a7c1CAS |

[35]  M. Winter, WebElements Periodic Table (Professional Edition). Available at http://www.webelements.com.

[36]  T.-H. Huang, M.-H. Zhang, Inorg. Chim. Acta 2014, 416, 28.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXos1Gmur4%3D&md5=48ecd59af1ddb71e588a799eaff01ed9CAS |

[37]  Q.-L. Ni, X.-F. Jiang, L.-C. Gui, X.-J. Wang, K.-G. Yang, X.-S. Bi, New J. Chem. 2011, 35, 2471.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtlOjtrvE&md5=eb5ac4b6377a5f28788e1b3364c66b21CAS |

[38]  X. Liu, H. Nan, W. Sun, Q. Zhang, M. Zhan, L. Zou, Z. Xie, X. Li, C. Lu, Y. Cheng, Dalton Trans. 2012, 41, 10199.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhtFKnsLzM&md5=3325d1df1ea497af616d784110a2f2ffCAS | 22772090PubMed |

[39]  G. F. Manbeck, W. W. Brennessel, R. Eisenberg, Inorg. Chem. 2011, 50, 3431.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXjs1SjsLk%3D&md5=54f8a2363786954341c122d2a4bc7e06CAS | 21417454PubMed |

[40]  M. G. Crestani, G. F. Manbeck, W. W. Brennessel, T. M. McCormick, R. Eisenberg, Inorg. Chem. 2011, 50, 7172.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXotlGgsbc%3D&md5=869fd4ee9a2efff31c7e5f2afce8e1c5CAS | 21714488PubMed |

[41]  A. Makal, J. Benedict, E. Trzop, J. Sokolow, B. Fournier, Y. Chen, J. A. Kalinowski, T. Graber, R. Henning, P. Coppens, J. Phys. Chem. A 2012, 116, 3359.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xjt1SqsLc%3D&md5=f14678fd5dc6fea9d98d0672a8859625CAS | 22385365PubMed |

[42]  G. B. Shaw, C. D. Grant, H. Shirota, E. W. Castner, G. J. Meyer, L. X. Chen, J. Am. Chem. Soc. 2007, 129, 2147.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXptVGmsQ%3D%3D&md5=9ca3b982f8181a416144971e5c24e191CAS | 17256860PubMed |

[43]  K. A. Vinogradova, V. F. Plyusnin, A. S. Kupryakov, M. I. Rakhmanova, N. V. Pervukhina, D. Y. Naumov, L. A. Sheludyakova, E. B. Nikolaenkova, V. P. Krivopalov, M. B. Bushuev, Dalton Trans. 2014, 43, 2953.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhtVOmurc%3D&md5=712f84d83cbbd56eed06a3835dddeec3CAS | 24346321PubMed |

[44]  D. M. Zink, D. Volz, T. Baumann, M. Mydlak, H. Flügge, J. Friedrichs, M. Nieger, S. Bräse, Chem. Mater. 2013, 25, 4471.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhs1CgtrjE&md5=d92697f10c7798cd8701e446180ed7aaCAS |

[45]  C. Femoni, S. Muzzioli, A. Palazzi, S. Stagni, S. Zacchini, F. Monti, G. Accorsi, M. Bolognesi, N. Armaroli, M. Massi, G. Valenti, M. Marcaccio, Dalton Trans. 2013, 42, 997.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhvVOrtb%2FF&md5=b6ad2d0e6205843d398e98530f65ebc9CAS | 23108182PubMed |

[46]  A. Kaeser, M. Mohankumar, J. Mohanraj, F. Monti, M. Holler, J.-J. Cid, O. Moudam, I. Nierengarten, L. Karmazin-Brelot, C. Duhayon, B. Delavaux-Nicot, N. Armaroli, J.-F. Nierengarten, Inorg. Chem. 2013, 52, 12140.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhsFGrs7nK&md5=d5c5091d3aa77f8d8eecf480750e5feeCAS | 24083360PubMed |

[47]  A. J. M. Miller, J. L. Dempsey, J. C. Peters, Inorg. Chem. 2007, 46, 7244.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXosVCrs70%3D&md5=eaa6ded1d1adbb22abf5bf0ad115b6caCAS |

[48]  X.-L. Xin, M. Chen, Y.-b. Ai, F.-l. Yang, X.-L. Li, F. Li, Inorg. Chem. 2014, 53, 2922.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXivFWhsLw%3D&md5=ff7653d556c108b87f1d8df3ec2e31e8CAS | 24559388PubMed |

[49]  D. M. Zink, T. Baumann, J. Friedrichs, M. Nieger, S. Bräse, Inorg. Chem. 2013, 52, 13509.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhslGgsrzK&md5=99ea0251b554bb28f1fcc641a5425f93CAS | 24205840PubMed |

[50]  B. Bozic-Weber, V. Chaurin, E. C. Constable, C. E. Housecroft, M. Meuwly, M. Neuburger, J. A. Rudd, E. Schonhofer, L. Siegfried, Dalton Trans. 2012, 41, 14157.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xhs1aku7jK&md5=9c5006527620c8587e23db3d4997b5ebCAS | 23034733PubMed |

[51]  B. Bozic-Weber, E. C. Constable, C. E. Housecroft, M. Neuburger, J. R. Price, Dalton Trans. 2010, 39, 3585.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXjvFKgtLk%3D&md5=65952557a261e460e02e7a8edd34f288CAS | 20354612PubMed |

[52]  C. L. Linfoot, P. Richardson, T. E. Hewat, O. Moudam, M. M. Forde, A. Collins, F. White, N. Robertson, Dalton Trans. 2010, 39, 8945.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtFygtbfI&md5=24a6e846c0fbe1cdb46ca2cbb214857fCAS | 20859569PubMed |