Skip to main content
Log in

Synthesis, characterization and H2 adsorption performances of polymeric Co(II) and Ni(II) complexes of pyrazine-2,3-dicarboxylic acid and 1-vinylimidazole

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

We studied the synthesis and characterization of polymeric coordination complexes of Co(II) and Ni(II) ions with pyrazine-2,3-dicarboxylic acid and 1-vinylimidazole. The e lemental analysis, infrared spectroscopy, powder X-ray diffraction, magnetic susceptibility, thermal analysis and X-ray single crystal techniques were used in the characterization. The X-ray single crystal analysis suggests that the pyrazine-2,3-dicarboxylato ligand acts as a bridging ligand through the oxygen atoms of the carboxylate groups and the nitrogen atoms on the pyrazine ring. The 1-vinylimidazole ligand behaves as a monodentate ligand via the ring nitrogen atom. Further, the H2 adsorption studies were carried out at 75 K for various increasing pressures and the highest H2 adsorption performances for Co(II) and Ni(II) complexes were estimated as 2.66 and 2.99 wt% at 87 bar. The theoretical calculations using the crystal data were also performed to determine the voids in the structure of Co(II) complex.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. N.C. Burtch, H. Jasuja, K.S. Walton, Chem. Rev. 114, 10575 (2014)

    Article  CAS  PubMed  Google Scholar 

  2. D. Gygi, E.D. Bloch, J.A. Mason, M.R. Hudson, M.I. Gonzalez, R.L. Siegelman, T.A. Darwish, W.L. Queen, C.M. Brown, J.R. Long, Chem. Mater. 28, 1128 (2016)

    Article  CAS  Google Scholar 

  3. Y.-P. Gao, L. Guo, Y.-H. Lv, W. Dong, M. Jia, F. Chang, J. Coord. Chem. 69, 3745 (2016)

    Article  CAS  Google Scholar 

  4. P. Yang, D. Wang, J. Sun, F. Zhai, Z. Chen, Y. Ling, Y. Zhou, Inorg. Chim. Acta 447, 1 (2016)

    Article  CAS  Google Scholar 

  5. F. Yu, X. Xiong, K. Huang, Y. Zhou, B. Li, CrystEngComm 19, 2126 (2017)

    Article  CAS  Google Scholar 

  6. W.-X. Li, H.-X. Li, H.-Y. Li, M.-M. Chen, Y.-X. Shi, J.-P. Lang, Cryst. Growth Des. 17, 3948 (2017)

    Article  CAS  Google Scholar 

  7. J. Zhao, Y. Yang, X. Han, C. Liang, J. Liu, X. Song, Z. Ge, Z. Liu, A.C.S. Appl, Mater. Interfaces 9, 23555 (2017)

    Article  CAS  Google Scholar 

  8. J.M. Cardoso, A.M. Galvão, S.I. Guerreiro, J.H. Leitão, A.C. Suarez, M.F.N. Carvalho, Dalton Trans. 45, 7114 (2016)

    Article  CAS  PubMed  Google Scholar 

  9. L.J. Murray, M. Dincă, J.R. Long, Chem. Soc. Rev. 38, 1294 (2009)

    Article  CAS  PubMed  Google Scholar 

  10. Y. Noori, K. Akhbari, RSC Adv. 7, 1782 (2017)

    Article  CAS  Google Scholar 

  11. D. Braga, L. Brammer, N.R. Champness, CrystEngComm 7, 1 (2005)

    Article  CAS  Google Scholar 

  12. H. Deng, S. Grunder, K. Cordova, C. Valente, H. Furukawa, M. Hmadeh, F. Gándara, A. Whalley, Z. Liu, S. Asahina, Science 336, 1018 (2012)

    Article  CAS  Google Scholar 

  13. M. Du, C.-P. Li, C.-S. Liu, S.-M. Fang, Coord. Chem. Rev. 257, 1282 (2013)

    Article  CAS  Google Scholar 

  14. A.Y. Robin, K.M. Fromm, Coord. Chem. Rev. 250, 2127 (2006)

    Article  CAS  Google Scholar 

  15. S.L. James, Chem. Soc. Rev. 32, 276 (2003)

    Article  CAS  PubMed  Google Scholar 

  16. F. Guo, B. Zhu, M. Liu, X. Zhang, J. Zhang, J. Zhao, CrystEngComm 15, 6191 (2013)

    Article  CAS  Google Scholar 

  17. H.-Y. Lin, J. Luan, X.-L. Wang, J.-W. Zhang, G.-C. Liu, A.-X. Tian, RSC Adv. 4, 62430 (2014)

    Article  CAS  Google Scholar 

  18. B.-H. Ye, M.-L. Tong, X.-M. Chen, Coord. Chem. Rev. 249, 545 (2005)

    Article  CAS  Google Scholar 

  19. L.-N. Jin, Q. Liu, W.-Y. Sun, CrystEngComm 16, 3816 (2014)

    Article  CAS  Google Scholar 

  20. C.-S. Liu, J.-J. Wang, L.-F. Yan, Z. Chang, X.-H. Bu, E.C. Sañudo, J. Ribas, Inorg. Chem. 46, 6299 (2007)

    Article  CAS  PubMed  Google Scholar 

  21. X. Feng, W. Chen, B. Xiang, J. Coord. Chem. 69, 1551 (2016)

    Article  CAS  Google Scholar 

  22. S.-L. Cai, S. Wang, Z.-H. He, K. Zhang, M.-L. Li, J. Fan, S.-R. Zheng, W.-G. Zhang, Z. Anorg, Allg. Chem. 643, 593 (2017)

    Article  CAS  Google Scholar 

  23. W. Lu, Z. Wei, Z.-Y. Gu, T.-F. Liu, J. Park, J. Park, J. Tian, M. Zhang, Q. Zhang, T. Gentle III, Chem. Soc. Rev. 43, 5561 (2014)

    Article  CAS  PubMed  Google Scholar 

  24. R. Kitaura, K. Fujimoto, S.I. Noro, M. Kondo, S. Kitagawa, Angew. Chem. Int. Ed. 41, 133 (2002)

    Article  CAS  Google Scholar 

  25. S. Taşcıoğlu, A. Aydın, B. Yalçın, E. Kakı, Ö. Andaç, O. Büyükgüngör, B. Koşar, Polyhedron 30, 2171 (2011)

    Article  CAS  Google Scholar 

  26. F. Nepveu, M. Berkaoui, L. Walz, Acta Crystallogr. Sect. C 49, 1465 (1993)

    Article  Google Scholar 

  27. C.J. O’Connor, C.L. Klein, R.J. Majeste, L.M. Trefonas, Inorg. Chem. 21, 64 (1982)

    Article  Google Scholar 

  28. M. Tombul, K. Güven, I. Svoboda, Acta Crystallogr. Sect. E 64, 246 (2008)

    Article  CAS  Google Scholar 

  29. F. Takusagawa, A. Shimada, Chem. Lett. 2, 1121 (1973)

    Article  Google Scholar 

  30. G. Günay, O.Z. Yeşilel, C. Darcan, S. Keskin, O. Büyükgüngör, Inorg. Chim. Acta 399, 19 (2013)

    Article  CAS  Google Scholar 

  31. Y.Q. Sun, L. Wu, L.L. Fan, G.Y. Zhang, Y.Y. Xu, D.Z. Gao, Z. Anorg, Allg. Chem. 638, 427 (2012)

    Article  CAS  Google Scholar 

  32. G. Günay, O.Z. Yeşilel, M.S. Soylu, S. Keskin, H. Dal, Synth. Met. 161, 2471 (2011)

    Article  CAS  Google Scholar 

  33. X.-H. Li, Q. Shi, M.-L. Hu, H.-P. Xiao, Inorg. Chem. Commun. 7, 912 (2004)

    Article  CAS  Google Scholar 

  34. Y. Ma, Y.-K. He, Z.-B. Han, Acta Crystallogr. Sect. E 62, 2528 (2006)

    Article  CAS  Google Scholar 

  35. O.Z. Yeşilel, A. Mutlu, O. Büyükgüngör, Polyhedron 27, 2471 (2008)

    Article  CAS  Google Scholar 

  36. T. Okubo, M. Kondo, S. Kitagawa, Synth. Met. 85, 1661 (1997)

    Article  CAS  Google Scholar 

  37. G.G. Sezer, O.Z. Yeşilel, O. Büyükgöngör, J. Mol. Struct. 1137, 562 (2017)

    Article  CAS  Google Scholar 

  38. X.-M. Lin, L. Chen, H.-C. Fang, Z.-Y. Zhou, X.-X. Zhou, J.-Q. Chen, A.-W. Xu, Y.-P. Cai, Inorg. Chim. Acta 362, 2619 (2009)

    Article  CAS  Google Scholar 

  39. Y. Kubota, M. Takata, R. Matsuda, R. Kitaura, S. Kitagawa, K. Kato, M. Sakata, T.C. Kobayashi, Angew. Chem. Int. Ed. 44, 920 (2005)

    Article  CAS  Google Scholar 

  40. M. Gryz, W. Starosta, J. Leciejewicz, J. Coord. Chem. 58, 931 (2005)

    Article  CAS  Google Scholar 

  41. J.Y. Lu, Coord. Chem. Rev. 246, 327 (2003)

    Article  CAS  Google Scholar 

  42. R.A. Agarwal, N.K. Gupta, Coord. Chem. Rev. 332, 100 (2017)

    Article  CAS  Google Scholar 

  43. S. Ghosh, F. Ahmed, G.G. Hossain, D.T. Haworth, S.E. Kabir, J. Chem. Crystallogr. 39, 702 (2009)

    Article  CAS  Google Scholar 

  44. Y.-P. Tong, G.-T. Luo, J. Zhen, Y. Shen, H.-R. Liu, Cryst. Growth Des. 13, 446 (2013)

    Article  CAS  Google Scholar 

  45. F. Şen, R. Şahin, M. Dinçer, Ö. Andaç, M. Taş, J. Crystallogr. 2014, 1 (2014)

    Google Scholar 

  46. H. Yilmaz, O. Andac, S. Gorduk, Polyhedron 133, 16 (2017)

    Article  CAS  Google Scholar 

  47. H. Yilmaz, S. Gorduk, O. Andac, Inorg. Chim. Acta 469, 154 (2018)

    Article  CAS  Google Scholar 

  48. A. Züttel, A. Borgschulte, L. Schlapbach, I. Chorkendorff, S. Suda, Hydrogen as a Future Energy Carrier (Wiley, Weinheim, 2008), pp. 71–147

    Book  Google Scholar 

  49. J.L. Rowsell, O.M. Yaghi, Angew. Chem. Int. Ed. 44, 4670 (2005)

    Article  CAS  Google Scholar 

  50. A.G. Wong-Foy, A.J. Matzger, O.M. Yaghi, J. Am. Chem. Soc. 128, 3494 (2006)

    Article  CAS  PubMed  Google Scholar 

  51. O.M. Yaghi, Q. Li, MRS Bull. 34, 682 (2009)

    Article  CAS  Google Scholar 

  52. M. Bastos-Neto, C. Patzschke, M. Lange, J. Möllmer, A. Möller, S. Fichtner, C. Schrage, D. Lässig, J. Lincke, R. Staudt, Energy Environ. Sci. 5, 8294 (2012)

    Article  CAS  Google Scholar 

  53. A.F. Dalebrook, W. Gan, M. Grasemann, S. Moret, G. Laurenczy, Chem. Commun. 49, 8735 (2013)

    Article  CAS  Google Scholar 

  54. X. Wu, R. Wang, H. Yang, W. Wang, W. Cai, Q. Li, J. Mater. Chem. A 3, 10724 (2015)

    Article  CAS  Google Scholar 

  55. P. Kumar, K.-H. Kim, E.E. Kwon, J.E. Szulejko, J. Mater. Chem. A 4, 345 (2016)

    Article  CAS  Google Scholar 

  56. S. Demir, H.M. Çepni, Y. Topcu, M. Hołyńska, S. Keskin, Inorg. Chim. Acta 427, 138 (2015)

    Article  CAS  Google Scholar 

  57. D. Saha, T. Maity, S. Koner, Eur. J. Inorg. Chem. 2015, 1053 (2015)

    Article  CAS  Google Scholar 

  58. S. Rahali, M. Seydou, Y. Belhocine, F. Maurel, B. Tangour, Int. J. Hydrogen Energy 41, 2711 (2016)

    Article  CAS  Google Scholar 

  59. G.M. Sheldrick, SHELX-97: Programs for Crystal Structure Analysis (University of Göttingen, Germany, 1997)

    Google Scholar 

  60. G.M. Sheldrick, Acta Crystallogr. Sect. A 64, 112 (2008)

    Article  CAS  Google Scholar 

  61. L. Farrugia, J. Appl. Crystallogr. 30, 565 (1997)

    Article  CAS  Google Scholar 

  62. O.Z. Yeşilel, A. Mutlu, O. Büyükgüngör, Polyhedron 28, 437 (2009)

    Article  CAS  Google Scholar 

  63. O.Z. Yeşilel, A. Mutlu, C. Darcan, O. Büyükgüngör, J. Mol. Struct. 964, 39 (2010)

    Article  CAS  Google Scholar 

  64. Y. Baran, W. Linert, J. Chem. Crystallogr. 29, 1077 (1999)

    Article  CAS  Google Scholar 

  65. F. Semerci, O.Z. Yeşilel, M.S. Soylu, S. Keskin, O. Büyükgöngür, Polyhedron 50, 314 (2013)

    Article  CAS  Google Scholar 

  66. L.V. Baikalova, V.I. Sokol, I.A. Zyryanova, I.V. Fedyanin, V.N. Khrustalev, E.A. Zelbst, O.A. Tarasova, V.S. Sergienko, B.A. Trofimov, Russ. J. Gen. Chem. 76, 791 (2006)

    Article  CAS  Google Scholar 

  67. M.-J. Fang, M.-X. Li, X. He, M. Shao, W. Pang, S.-R. Zhu, J. Mol. Struct. 921, 137 (2009)

    Article  CAS  Google Scholar 

  68. H.W. Langmi, J. Ren, B. North, M. Mathe, D. Bessarabov, Electrochim. Acta 128, 368 (2014)

    Article  CAS  Google Scholar 

  69. Y. Sun, H. Yu, L. Wang, W. Ding, J. Ji, Y. Chen, F. Ren, Z. Tian, Y. Zhao, L. Huang, P. Ren, R. Tang, J. Alloys Compd. 585, 667 (2014)

    Article  CAS  Google Scholar 

  70. P.D.C. Dietzel, B. Panella, M. Hirscher, R. Blom, H. Fjellvag, Chem. Commun. 9, 959 (2006)

    Article  CAS  Google Scholar 

  71. M. Arıcı, O.Z. Yeşilel, S. Keskin, M. Taş, Polyhedron 45, 103 (2012)

    Article  CAS  Google Scholar 

  72. M.L. Connolly, J. Appl. Crystallogr. 16, 548 (1983)

    Article  CAS  Google Scholar 

  73. T. Düren, F. Millange, G. Férey, K.S. Walton, R.Q. Snurr, J. Phys. Chem. C 111, 15350 (2007)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This study was supported by the Scientific and Technological Research Council of Turkey (TUBITAK) [Project Number: 110T131]. Thanks to Orhan BUYUKGUNGOR, Murat TAS, Selcuk DEMIR and Ramazan SAHIN for their contributions.

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Semih Gorduk or Hakan Yilmaz.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 797 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Andac, O., Gorduk, S. & Yilmaz, H. Synthesis, characterization and H2 adsorption performances of polymeric Co(II) and Ni(II) complexes of pyrazine-2,3-dicarboxylic acid and 1-vinylimidazole. J IRAN CHEM SOC 15, 1699–1708 (2018). https://doi.org/10.1007/s13738-018-1367-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-018-1367-2

Keywords

Navigation