Abstract
Two hydrogen-bonded organic frameworks of the composition [((CH3)2NH2)3.5(Ni-H4.5TPPP)]·DMF·H2O (1) and [((CH3)2NH2)4(Ni-H4TPPP)(H2O)3]·DMF·H2O (2) (Ni-HxTPPP is nickel(II) 5,10,15,20-tetrakis(4-phosphonatophenyl)porphyrinate, x is the number of protons of phosphonate groups, DMF is N,N-dimethylformamide) are obtained by crystallization of nickel(II) phosphonatophenylporphyrinate under solvothermal conditions. Crystal structures of 1 and 2 are determined by the single crystal X-ray diffraction analysis. Both frameworks are shown to be stabilized by the formation of numerous intermolecular hydrogen bonds. Partial deprotonation of phosphonate groups causes the formation of anionic frameworks whose charge is compensated by the presence of dimethylammonium cations being solvent destruction products. The system of hydrogen bonds in frameworks 1 and 2 is represented by 2D layers in the ab plane going parallel to open 1D channels. It is established that the occurrence of lattice water in framework 2 leads to an increase in the number of hydrogen bonds and bonding types of porphyrin phosphonate groups, which can affect the proton-conductive properties of the material.
Similar content being viewed by others
REFERENCES
S. Jeoung, S. Kim, M. Kim, and H. R. Moon. Coord. Chem. Rev., 2020, 420, 213377. https://doi.org/10.1016/j.ccr.2020.213377
N. Huang, P. Wang, and D. Jiang. Nat. Rev. Mater., 2016, 1(10), 16068. https://doi.org/10.1038/natrevmats.2016.68
B. Wang, R. B. Lin, Z. Zhang, S. Xiang, and B. Chen. J. Am. Chem. Soc., 2020, 142(34), 14399-14416. https://doi.org/10.1021/jacs.0c06473
C. Stackhouse, J. Ren, C. Shan, A. Nafady, A. M. Al-Enizi, M. Ubaidullah, Z. Niu, and S. Ma. Cryst. Growth Des., 2019, 19(11), 6377-6380. https://doi.org/10.1021/acs.cgd.9b00851
Q. Yin, Y.-L. Li, L. Li, J. Lü, T.-F. Liu, and R. Cao. ACS Appl. Mater. Interfaces, 2019, 11(19), 17823-17827. https://doi.org/10.1021/acsami.9b03696
X. Zhang, L. Li, J.-X. Wang, H.-M. Wen, R. Krishna, H. Wu, W. Zhou, Z.-N. Chen, B. Li, G. Qian, and B. Chen. J. Am. Chem. Soc., 2020, 142(1), 633-640. https://doi.org/10.1021/jacs.9b12428
S. Cai, H. Shi, Z. Zhang, X. Wang, H. Ma, N. Gan, Q. Wu, Z. Cheng, K. Ling, M. Gu, C. Ma, L. Gu, Z. An, and W. Huang. Angew. Chem., Int. Ed., 2018, 57(15), 4005-4009. https://doi.org/10.1002/anie.201800697
Y. Han, T. Zhang, X. Chen, Q. Chen, J. Hao, W. Song, Y. Zeng, and P. Xue. ACS Appl. Mater. Interfaces, 2021, 13(27), 32270-32277. https://doi.org/10.1021/acsami.1c08316
W. Gong, D. Chu, H. Jiang, X. Chen, Y. Cui, and Y. Liu. Nat. Commun., 2019, 10(1), 600. https://doi.org/10.1038/s41467-019-08416-6
S. A. Kuznetsova, A. S. Gak, Y. V. Nelyubina, V. A. Larionov, H. Li, M. North, V. P. Zhereb, A. F. Smolyakov, A. O. Dmitrienko, M. G. Medvedev, I. S. Gerasimov, A. S. Saghyan, and Y. N. Belokon. Beilstein J. Org. Chem., 2020, 16, 1124-1134. https://doi.org/10.3762/bjoc.16.99
X.-T. He, Y.-H. Luo, D.-L. Hong, F.-H. Chen, Z.-Y. Zheng, C. Wang, J.-Y. Wang, C. Chen, and B.-W. Sun. ACS Appl. Nano Mater., 2019, 2(4), 2437-2445. https://doi.org/10.1021/acsanm.9b00303
W. Liang, F. Carraro, M. B. Solomon, S. G. Bell, H. Amenitsch, C. J. Sumby, N. G. White, P. Falcaro, and C. J. Doonan. J. Am. Chem. Soc., 2019, 141(36), 14298-14305. https://doi.org/10.1021/jacs.9b06589
G. Yücesan, Y. Zorlu, M. Stricker, and J. Beckmann. Coord. Chem. Rev., 2018, 369, 105-122. https://doi.org/10.1016/j.ccr.2018.05.002
T. Rhauderwiek, K. Wolkersdörfer, S. Øien-Ødegaard, K.-P. Lillerud, M. Wark, and N. Stock. Chem. Commun., 2018, 54(4), 389-392. https://doi.org/10.1039/C7CC07766A
T. Rhauderwiek, H. Zhao, P. Hirschle, M. Döblinger, B. Bueken, H. Reinsch, D. De Vos, S. Wuttke, U. Kolb, and N. Stock. Chem. Sci., 2018, 9(24), 5467-5478. https://doi.org/10.1039/C8SC01533C
B. Wang, T. Rhauderwiek, A. K. Inge, H. Xu, T. Yang, Z. Huang, N. Stock, and X. Zou. Chem. – Eur. J., 2018, 24(66), 17429-17433. https://doi.org/10.1002/chem.201804133
Y. Y. Enakieva, A. A. Sinelshchikova, M. S. Grigoriev, V. V. Chernyshev, K. A. Kovalenko, I. A. Stenina, A. B. Yaroslavtsev, Y. G. Gorbunova, and A. Y. Tsivadze. Chem. – Eur. J., 2019, 25(45), 10552-10556. https://doi.org/10.1002/chem.201902212
Y. Y. Enakieva, A. A. Sinelshchikova, M. S. Grigoriev, V. V. Chernyshev, K. A. Kovalenko, I. A. Stenina, A. B. Yaroslavtsev, Y. G. Gorbunova, and A. Y. Tsivadze. Chem. – Eur. J., 2021, 27(5), 1598-1602. https://doi.org/10.1002/chem.202003893
Y. Y. Enakieva, E. A. Zhigileva, A. N. Fitch, V. V. Chernyshev, I. A. Stenina, A. B. Yaroslavtsev, A. A. Sinelshchikova, K. A. Kovalenko, Y. G. Gorbunova, and A. Y. Tsivadze. Dalton Trans., 2021, 50, 6549-6560. https://doi.org/10.1039/d1dt00612f
M. M. Ayhan, C. Bayraktar, K. B. Yu, G. Hanna, A. O. Yazaydin, Y. Zorlu, and G. Yücesan. Chem. – Eur. J., 2020, 26(65), 14813-14816. https://doi.org/10.1002/chem.202001917
Y. Wang, J. Yin, D. Liu, C. Gao, Z. Kang, R. Wang, D. Sun, and J. Jiang. J. Mater. Chem. A, 2021, 9(5), 2683-2688. https://doi.org/10.1039/D0TA07207A
P. Tholen, C. A. Peeples, R. Schaper, C. Bayraktar, T. S. Erkal, M. M. Ayhan, B. Çoşut, J. Beckmann, A. O. Yazaydin, M. Wark, G. Hanna, Y. Zorlu, and G. Yücesan. Nat. Commun., 2020, 11(1), 3180. https://doi.org/10.1038/s41467-020-16977-0
Y. G. Gorbunova, Y. Y. Enakieva, M. V. Volostnykh, A. A. Sinelshchikova, I. A. Abdulaeva, K. P. Birin, and A. Y. Tsivadze. Russ. Chem. Rev., 2022, 91. https://doi.org/10.1070/RCR5038
X.-T. He, Y.-H. Luo, Z.-Y. Zheng, C. Wang, J.-Y. Wang, D.-L. Hong, L.-H. Zhai, L.-H. Guo, and B.-W. Sun. ACS Appl. Nano Mater., 2019, 2(12), 7719-7727. https://doi.org/10.1021/acsanm.9b01787
SAINT-Plus, version 8.40A. Madison, Wisconsin, USA: Bruker AXS Inc., 2019.
SADABS, version 2016/2. Madison, Wisconsin, USA: Bruker AXS Inc., 2016.
G. M. Sheldrick. Acta Crystallogr., Sect. A, 2008, 64(1), 112-122. https://doi.org/10.1107/S0108767307043930
G. M. Sheldrick. Acta Crystallogr., Sect. C: Struct. Chem., 2015, 71, 3-8. https://doi.org/10.1107/S2053229614024218
A. L. Spek. Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 2015, 71, 9-18. https://doi.org/10.1107/S2053229614024929
T. F. Willems, C. H. Rycroft, M. Kazi, J. C. Meza, and M. Haranczyk. Microporous Mesoporous Mater., 2012, 149(1), 134-141. https://doi.org/10.1016/j.micromeso.2011.08.020
V. A. Blatov, A. P. Shevchenko, and D. M. Proserpio. Cryst. Growth Des., 2014, 14(7), 3576-3586. https://doi.org/10.1021/cg500498k
R. I. Zubatyuk, A. A. Sinelshchikova, Y. Y. Enakieva, Y. G. Gorbunova, A. Y. Tsivadze, S. E. Nefedov, A. Bessmertnykh-Lemeune, R. Guilard, and O. V. Shishkin. CrystEngComm, 2014, 16(45), 10428-10438. https://doi.org/10.1039/C4CE01623H
M. A. Uvarova, A. A. Sinelshchikova, M. A. Golubnichaya, S. E. Nefedov, Y. Y. Enakieva, Y. G. Gorbunova, A. Y. Tsivadze, C. Stern, A. Bessmertnykh-Lemeune, and R. Guilard. Cryst. Growth Des., 2014, 14(11), 5976-5984. https://doi.org/10.1021/cg501157e
C. J. Kingsbury and M. O. Senge. Coord. Chem. Rev., 2021, 431, 213760. https://doi.org/10.1016/j.ccr.2020.213760
Funding
The work was supported by the Ministry of Science and Higher Education of the Russian Federation.
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
The authors declare that they have no conflicts of interests.
Additional information
Russian Text © The Author(s), 2022, published in Zhurnal Strukturnoi Khimii, 2022, Vol. 63, No. 6, pp. 739-750.https://doi.org/10.26902/JSC_id92283
Rights and permissions
About this article
Cite this article
Sinelshchikova, A.A., Enakieva, Y.Y., Grigoriev, M.S. et al. STRUCTURAL FEATURES OF HYDROGEN- BONDED ORGANIC FRAMEWORKS BASED ON NICKEL(II) 5,10,15,20-TETRAKIS(4- PHOSPHONATOPHENYL)PORPHYRINATE. J Struct Chem 63, 874–884 (2022). https://doi.org/10.1134/S002247662206004X
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S002247662206004X