Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Assembly and Properties of Four New Metal–Organic Complexes Based on 1,4-Naphthalenedicarboxylate: Effect of Four Bis-pyridyl-bis-amide Ligands with Diverse Spacers in the Structures

Hong-Yan Lin A , Xun-Zhang Zhao A , Ling Zeng A , Qing-Lin Wang A , Xiu-Li Wang A B and Guo-Cheng Liu A
+ Author Affiliations
- Author Affiliations

A Department of Chemistry, Bohai University, Jinzhou 121000, China.

B Corresponding author. Email: wangxiuli@bhu.edu.cn

Australian Journal of Chemistry 68(10) 1550-1561 https://doi.org/10.1071/CH15110
Submitted: 6 March 2015  Accepted: 16 April 2015   Published: 15 May 2015

Abstract

Four new complexes based on 1,4-naphthalenedicarboxylic acid (1,4-H2NDC) and four bis-pyridyl-bis-amide ligands with various spacers (3-bpye = N,N′-bis(3-pyridinecarboxamide)-1,2-ethane; 3-bpfp = bis(3-pyridylformyl)piperazine; 3-bpcd = N,N′-bis(pyridin-3-yl)cyclohexane-1,4-dicarboxamide; and 3-bpcb = N,N′-bis(3-pyridinecarboxamide)-1,4-benzene), namely [Cu2(1,4-NDC)2(3-bpye)(H2O)] (1), [Cu(1,4-NDC)(3-bpfp)0.5] (2), [Cu3(1,4-NDC)3(3-bpcd)3]·2H2O (3), and [Cu(1,4-NDC)(3-bpcb)] (4), have been hydrothermally synthesized. Complex 1 is a 3D coordination network and represents an 8-connected {420.68} topology. Complex 2 shows a 2-fold interpenetrating 3D architecture with a 6-connected {412.63} topology. Complexes 3 and 4 possess similar 2D sql layers with the {44.62} topology, but the coordination modes of 1,4-NDC ligands and the conformations of the two bis-pyridyl-bis-amide ligands are different. The adjacent layers for 3 and 4 are further linked by hydrogen bonding interactions to form 3D supramolecular networks. The successful assemblies of complexes 14 imply that by using the different bis-pyridyl-bis-amide ligands with diverse spacers can produce diverse metal–organic networks. Furthermore, the fluorescence and photocatalytic properties of complexes 14 have been investigated.


References

[1]  J. P. Zhao, W. C. Song, R. Zhao, Q. Yang, B. W. Hu, X. H. Bu, Cryst. Growth Des. 2013, 13, 2858.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXosFygsrg%3D&md5=3342376b679c54a53d14c6e933195a7bCAS |

[2]  J. Liu, P. K. Thallapally, B. P. McGrail, D. R. Brown, J. Liu, Chem. Soc. Rev. 2012, 41, 2308.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XivFWlsbo%3D&md5=5ab3a1db8a2298d5018056e1f8e00b29CAS | 22143077PubMed |

[3]  J. R. Li, J. Sculley, H. C. Zhou, Chem. Rev. 2012, 112, 869.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXht1OnsbbL&md5=5ec90b8befbfe50c3a8c3534a742d5cfCAS | 21978134PubMed |

[4]  K. S. Jeong, Y. B. Go, S. M. Shin, S. J. Lee, J. Kim, O. M. Yaghi, N. Jeong, Chem. Sci. 2011, 2, 877.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXks1ais7w%3D&md5=16d6f36df4b56b0f049d46a9703132c9CAS |

[5]  C. H. Lee, J. Y. Wu, G. H. Lee, S. M. Peng, J. C. Jiang, K. L. Lu, Cryst. Growth Des. 2014, 14, 5608.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhsF2nurbI&md5=f481db29a533fbea488f1df3a7487c41CAS |

[6]  Q. Chen, Z. Chang, W. C. Song, H. Song, H. B. Song, T. L. Hu, X. H. Bu, Angew. Chem., Int. Ed. 2013, 52, 11550.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhsVCnu7zJ&md5=60030c189d75afc2cffd00c8bc62ea62CAS |

[7]  S. Pramanik, C. Zheng, X. Zhang, T. J. Emge, J. Li, J. Am. Chem. Soc. 2011, 133, 4153.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXivVChtr8%3D&md5=e89d21e8d8e4114c32f45ed177a71903CAS | 21384862PubMed |

[8]  X. H. Jing, X. C. Yi, E. Q. Gao, V. A. Blatov, Dalton Trans. 2012, 41, 14316.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhslClurvN&md5=929ddfd5323723c3b970171ce97a6949CAS | 23042587PubMed |

[9]  Y. H. Liao, W. Hsu, C. C. Yang, C. Y. Wu, J. D. Chen, J. C. Wang, CrystEngComm 2013, 15, 3974.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXnsVWksbY%3D&md5=f8f1f629cee324021d6e5d86f9177cf2CAS |

[10]  D. X. Ma, B. Y. Li, X. J. Zhou, Q. Zhou, K. Liu, G. Zeng, G. H. Li, Z. Shi, S. H. Feng, Chem. Commun. 2013, 49, 8964.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhsVehtr7J&md5=6a228e8589c139a5b59675e8f80a3a50CAS |

[11]  C. Wang, T. Zhang, W. Lin, Chem. Rev. 2012, 112, 1084.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhsVCgtL3F&md5=284db6ef10d8bbaebff10763ca15551dCAS | 22070202PubMed |

[12]  L. Rajput, D. Kim, M. S. Lah, CrystEngComm 2013, 15, 259.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhvVSmtrbM&md5=21ac7beace5d9035575d326935ffdbc0CAS |

[13]  X. Q. Liang, X. H. Zhou, C. Chen, H. P. Xiao, Y. Z. Li, J. L. Zuo, X. Z. You, Cryst. Growth Des. 2009, 9, 1041.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXpsF2m&md5=e8a5db2ef1b41b6ee055f5209ce79f9eCAS |

[14]  W. L. Zhang, Y. Liu, J. F. Ma, Cryst. Growth Des. 2008, 8, 1250.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXis1KgtL0%3D&md5=875f4a8c629e0ace752b1548d89aa3f5CAS |

[15]  J. J. Wang, T. L. Hu, X. H. Bu, CrystEngComm 2011, 13, 5152.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtVOlurbP&md5=04e2d45c83eea8c30f61419911334054CAS |

[16]  K. L. Huang, X. Liu, G. M. Liang, Inorg. Chim. Acta 2009, 362, 1565.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXisFSqsb8%3D&md5=468f7268fb98ffca13ed8420e47fd2abCAS |

[17]  N. W. Ockwig, O. Delgado-Friedrichs, M. O’Keeffe, O. M. Yaghi, Acc. Chem. Res. 2005, 38, 176.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXksFSgsg%3D%3D&md5=1301dfd746e6325c1d3769913122f101CAS | 15766236PubMed |

[18]  S. S. Y. Chui, S. M. F. Lo, J. P. H. Charmant, G. A. Orpen, I. D. Williams, Science 1999, 283, 1148.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXhsFeitLc%3D&md5=0475cb1bc37a444f3f82bdb68c1681c1CAS |

[19]  Z. X. Wang, B. S. Zheng, H. T. Liu, X. Lin, X. Y. Yu, P. G. Yi, R. R. Yun, Cryst. Growth Des. 2013, 13, 5001.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhsFOisrnI&md5=623637a45da827ce56f0f7af2b5c072bCAS |

[20]  G. B. Li, L. Li, J. M. Liu, T. Yang, C. Y. Su, Cryst. Growth Des. 2013, 13, 1518.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXjslGhtLY%3D&md5=03e0cf380a200146b3920270485d2fa8CAS |

[21]  P. C. Cheng, P. T. Kuo, M. Y. Xie, W. Hsu, J. D. Chen, CrystEngComm 2013, 15, 6264.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtFWktLzN&md5=927a5872d84f273d769cfe2f28937253CAS |

[22]  X. Zhang, L. Hou, B. Liu, L. Cui, Y. Y. Wang, B. Wu, Cryst. Growth Des. 2013, 13, 3177.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXosVejs7s%3D&md5=a365997875da37042576ad1de8f6dc5cCAS |

[23]  Y. Gong, T. Wu, P. G. Jiang, J. H. Lin, Y. X. Yang, Inorg. Chem. 2013, 52, 777.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXjvVKk&md5=8e568b4357e444516607ce513d54d26bCAS | 23276292PubMed |

[24]  H. M. He, F. X. Sun, J. T. Jia, Z. Bian, N. Zhao, X. P. Qiu, L. X. Gao, G. S. Zhu, Cryst. Growth Des. 2014, 14, 4258.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhtleqt73I&md5=162c5131f22b4578f00b239ae9885a26CAS |

[25]  X. L. Zhao, W. Y. Sun, CrystEngComm 2014, 16, 3247.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXltFGqsb0%3D&md5=e9bb835e17aaf7040589548579cc7f33CAS |

[26]  G. L. Liu, Y. J. Qin, L. Jing, G. Y. Wei, H. Li, Chem. Commun. 2013, 49, 1699.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhslaksbY%3D&md5=90d473ae8bd190a8225425160842224dCAS |

[27]  T. K. Maji, M. Ohba, S. Kitagawa, Inorg. Chem. 2005, 44, 9225.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtFCmtb7J&md5=54219fd12230a6cda6f6f1e4dce31fb9CAS | 16323903PubMed |

[28]  X. L. Wang, J. Luan, H. Y. Lin, M. Le, G. C. Liu, Dalton Trans. 2014, 43, 8072.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXotF2itbs%3D&md5=c54afae220858aeb82a7e0cab5b4625aCAS | 24723145PubMed |

[29]  X. L. Wang, H. Y. Lin, B. Mu, A. X. Tian, G. C. Liu, N. H. Hu, CrystEngComm 2011, 13, 1990.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXjt12htrY%3D&md5=6e3c0b3149e40bcc81ccff5524535424CAS |

[30]  X. L. Wang, F. F. Sui, H. Y. Lin, J. W. Zhang, G. C. Liu, Cryst. Growth Des. 2014, 14, 3438.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXps1Srur0%3D&md5=9fd92db70fd12ebff40b20cf800261deCAS |

[31]  X. L. Wang, J. Luan, Q. L. Lu, H. Y. Lin, C. Xu, G. C. Liu, J. Organomet. Chem. 2013, 740, 17.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtVCqs7%2FI&md5=4b15cf2bc0a538d8fb57d9b2dddd8543CAS |

[32]  Y. H. Luo, X. Y. Yu, J. J. Yang, H. Zhang, CrystEngComm 2014, 16, 47.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhvVGntLfF&md5=70d1b8564e8ad881abe47bc3c69dc787CAS |

[33]  G. S. Yang, Y. Q. Lan, H. Y. Zang, K. Z. Shao, X. L. Wang, Z. M. Su, C. J. Jiang, CrystEngComm 2009, 11, 274.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhvVWlu78%3D&md5=8edc7e2e316625c2b83acf19a6f8bd2bCAS |

[34]  S. S. Chen, Y. Zhao, J. Fan, T. Okamura, Z. S. Bai, Z. H. Chen, W. Y. Sun, CrystEngComm 2012, 14, 3564.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XlvFGlsLY%3D&md5=5ab61d6029c010c2238796f63d644317CAS |

[35]  Y. Zuo, M. Fang, G. Xiong, P. F. Shi, B. Zhao, J. Z. Cui, P. Cheng, Cryst. Growth Des. 2012, 12, 3917.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhtVSmurbI&md5=2d9fb9228f6df4fa23e593d0af0449aaCAS |

[36]  S. L. Huang, X. X. Li, X. J. Shi, H. W. Hou, Y. T. Fan, J. Mater. Chem. 2010, 20, 5695.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXotVSrurs%3D&md5=f07c183352ec31dd10f49d386dd5a703CAS |

[37]  J. P. Zou, Q. Peng, Z. Wen, G. S. Zeng, Q. J. Xing, G. C. Guo, Cryst. Growth Des. 2010, 10, 2613.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXlt1WrsLo%3D&md5=e0c690275aa1a43db831c071fd86ff85CAS |

[38]  Y. J. Cui, Y. F. Yue, G. D. Qian, B. L. Chen, Chem. Rev. 2012, 112, 1126.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXnslKitr8%3D&md5=62d5c2347c77cd72f190680977963986CAS |

[39]  S. Q. Zang, Y. Su, Y. Z. Li, Z. P. Ni, Q. J. Meng, Inorg. Chem. 2006, 45, 174.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXht1ajsrvP&md5=dacadd2c0aaa543e1528a2ec88b2fc86CAS |

[40]  Y. Gong, T. Wu, J. H. Lin, B. S. Wang, CrystEngComm 2012, 14, 5649.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhtFWiu7nF&md5=293a72d33de2c15fd265ff952969792cCAS |

[41]  Y. Y. Liu, Z. H. Wang, J. Yang, B. Liu, Y. Y. Liu, J. F. Ma, CrystEngComm 2011, 13, 3811.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXmslajsbw%3D&md5=bd8d142a9eaeb1f21a000dc3858b2abbCAS |

[42]  J. Lu, J. X. Lin, X. L. Zhao, R. Cao, Chem. Commun. 2012, 48, 669.
         | Crossref | GoogleScholarGoogle Scholar |

[43]  B. Liu, Z. T. Yu, J. Yang, H. Wu, Y. Y. Liu, J. F. Ma, Inorg. Chem. 2011, 50, 8967.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtVWhtLvF&md5=1f2014545f8209e4303e2cea836a86bcCAS | 21842843PubMed |

[44]  Y. Q. Chen, G. R. Li, Y. K. Qu, Y. H. Zhang, K. H. He, Q. Gao, X. H. Bu, Cryst. Growth Des. 2013, 13, 901.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXntVemtQ%3D%3D&md5=1aca3dc5651f856ff602277a21e4bd34CAS |

[45]  T. Wen, D. X. Zhang, J. Liu, R. Lin, J. Zhang, Chem. Commun. 2013, 49, 5660.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXosVemsb8%3D&md5=c2eb6817ad90ae453772ef23b264e0c7CAS |

[46]  W. Q. Kan, B. Liu, J. Yang, Y. Y. Liu, J. F. Ma, Cryst. Growth Des. 2012, 12, 2288.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XlvFCru78%3D&md5=addbbb006bd4a876cff9214eec9e1187CAS |

[47]  C. Y. Sun, X. L. Wang, C. Qin, J. L. Jin, Z. M. Su, P. Huang, K. Z. Shao, Chem. – Eur. J. 2013, 19, 3639.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhslWrsrY%3D&md5=ac53fe02e448b7e53da8fbd2802f0fbdCAS | 23361638PubMed |

[48]  H. X. Yang, T. F. Liu, M. N. Cao, H. F. Li, S. Y. Gao, R. Cao, Chem. Commun. 2010, 46, 2429.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXjs1Gnur4%3D&md5=4d76b4ca8a480aedf816205a6195eb2cCAS |

[49]  S. Muthu, J. K. Yip, J. J. Vittal, J. Chem. Soc., Dalton Trans. 2002, 4561.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XptlOjtro%3D&md5=9ded1a61554ca0e5ca711ecfda9abc4bCAS |

[50]  H. W. Hou, Y. L. Song, H. Xu, Y. L. Wei, Y. T. Fan, Y. Zhu, L. K. Li, C. X. Du, Macromolecules 2003, 36, 999.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXksFCmtQ%3D%3D&md5=d6e004b405f92be7ec26410e8a0c1d6cCAS |

[51]  M. Sarkar, K. Biradha, Cryst. Growth Des. 2006, 6, 202.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXpvVSjsbg%3D&md5=19f1040c638d38895e7fbc54baa14c93CAS |

[52]  G. M. Sheldrick, Acta Crystallogr. Sect. A: Found. Crystallogr. 2008, 64, 112.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhsVGhurzO&md5=59f548f8f29686b585f885edea91b42eCAS |