Citation: Chuang LI, Yong-Ke HE, Na SHAO, Gang XIONG, Shuang-Yan WU, Li-Xin YOU, Ya-Guang SUN. Syntheses, Structures and Photoluminescence of Novel Lanthanide-organic Frameworks Based on 1, 4-Bis(3, 5-dicarboxylic pyrazol-1-ylmethyl) Benzene[J]. Chinese Journal of Structural Chemistry, ;2020, 39(5): 960-966. doi: 10.14102/j.cnki.0254-5861.2011-2537 shu

Syntheses, Structures and Photoluminescence of Novel Lanthanide-organic Frameworks Based on 1, 4-Bis(3, 5-dicarboxylic pyrazol-1-ylmethyl) Benzene

The Key Laboratory of Inorganic Molecule-based Chemistry of Liaoning Province, College of Applied Chemistry, Shenyang University of Chemical Technology, Shenyang 110142, China

Corresponding author: Yong-Ke HE, yk-h@163.com Ya-Guang SUN, sunyaguang@syuct.edu.cn
Received Date: 17 July 2019
Accepted Date: 28 October 2019

Fund Project: the National Natural Science Foundation of China 21701116the National Natural Science Foundation of China 21671139the National Natural Science Foundation of China 21501122the Doctor Scientiﬁc Research Foundation of Liaoning Province 201601201the Doctor Scientiﬁc Research Foundation of Liaoning Province 201601193Program for Liaoning Innovative Research Team in University 2018012

Figures(4)

Two isomorphic 3D lanthanide metal-organic frameworks, {[Tb(L)_0.5(OX)_0.5(H₂O)₂DMF]^.DMF}_n (1) and {[Dy(L)_0.5(OX)_0.5(H₂O)₂DMF]^.DMF}_n (2), have been prepared under solvothermal conditions based on 1, 4-bis(3, 5-dicarboxylicpyrazol-1-ylmethyl) benzene (H₄L), oxalis acid (H₂OX) and lanthanide ions. Compound 1 crystallizes in monoclinic system, space group P2₁/c with a = 9.418(15), b = 15.23(2), c = 14.47(2) Å, β = 100.07(3)°, V = 2044(5) Å³, Z = 4, M_r = 590.3 g/mol, D_c = 1.919 g/cm³, μ = 3.524 mm^-1, F(000) = 1168, R = 0.0893 and wR = 0.1902 for 3486 observed reflections (I > 2σ(I)). In compound 1, the central terbium(Ⅲ) ions are coordinated with eight atoms, and two neighboring terbium(Ⅲ) ions are linked together by one bridging oxalic acid group to give rise to a [Tb₂(OX)(L)₄] unit. Each [Tb₂(OX)(L)₄] unit connects to the surrounding six identical ones by the oxygen atoms bridging to lead to a 3D framework. Compound 1 exhibits strong luminescent emissions at the solid state owing to the antenna effect of the ligand.
- lanthanide-organic frameworks,
- luminescent emission,
- antenna effect
1. [1]
  Li, J. R.; Sculley, J.; Zhou, H. C. Metal-organic frameworks for separations. Chem. Rev. 2012, 112, 869–932. doi: 10.1021/cr200190s
2. [2]
  Silva, P.; FVilela, S. M.; Tome, J. P. C.; Almeida Paz, F. Á. Multifunctional metal-organic frameworks: from academia to industrial applications. Chem. Soc. Rev. 2015, 44, 6774–6803. doi: 10.1039/C5CS00307E
3. [3]
  Lustig, W. P.; Mukherjee, S.; Mukherjee, N. D.; Rudd, A. V.; Desai, J.; Li, S. K. Ghosh, metal-organic frameworks: functional luminescent and photonic materials for sensing applications. Chem. Soc. Rev. 2017, 46, 3242–3285. doi: 10.1039/C6CS00930A
4. [4]
  Zhang, Y. M.; Yuan, S.; Day, G.; Wang, X.; Yang, X. Y.; Zhou, H. C. Luminescent sensors based on metal-organic frameworks. Coord. Chem. Rev. 2018, 354, 28–45. doi: 10.1016/j.ccr.2017.06.007
5. [5]
  Cui, Y. J.; Yue, Y. F.; Qian, G. D.; Chen, B. L. Luminescent functional metal-organic frameworks. Chem. Rev. 2012, 112, 1126–1162. doi: 10.1021/cr200101d
6. [6]
  Hu, Z. C.; Deibert, B. J.; Li, J. Luminescent metal-organic frameworks for chemical sensing and explosive detection. Chem. Soc. Rev. 2014, 43, 5815–5840. doi: 10.1039/C4CS00010B
7. [7]
  Karmakar, A.; Samanta, P.; Desai, A. V.; Ghosh, S. K. Guest responsive metal-organic frameworks as scaffolds for separation and sensing applications. Acc. Chem. Res. 2017, 50, 2457–2469. doi: 10.1021/acs.accounts.7b00151
8. [8]
  Yan, B. Lanthanide-functionalized metal-organic framework hybrid systems to create multiple luminescent centers for chemical sensing. Acc. Chem. Res. 2017, 50, 2789–2798. doi: 10.1021/acs.accounts.7b00387
9. [9]
  Heine, J.; Müller-Buschbaum, K. Engineering metal-based luminescence in coordination polymers and metal-organic frameworks. Chem. Soc. Rev. 2013, 42, 9232–9242. doi: 10.1039/c3cs60232j
10. [10]
  Karmakar, A.; Samanta, P.; Desai, A. V.; Ghosh, S. K. Guest-responsive metal-organic frameworks as scaffolds for separation and sensing applications. Acc. Chem. Res. 2017, 50, 2457–2469. doi: 10.1021/acs.accounts.7b00151
11. [11]
  Ye, J. W.; Zhou, H. L.; Liu, S. Y.; Cheng, X. N.; Lin, R. B.; Qi, X. L.; Zhang, J. P.; Chen, X. M. Encapsulating pyrene in a metal-organic zeolite for optical sensing of molecular oxygen. Chem. Mater. 2015, 27, 8255–8260. doi: 10.1021/acs.chemmater.5b03955
12. [12]
  Zhang, S. Y.; Shi, W.; Cheng, P.; Zaworotko, M. J. A mixed-crystal lanthanide zeolite-like metal-organic framework as a fluorescent indicator for lysophosphatidic acid, a cancer biomarker. J. Am. Chem. Soc. 2015, 137, 12203–12206. doi: 10.1021/jacs.5b06929
13. [13]
  Zhou, J. M.; Li, H. H.; Zhang, H.; Shi, H. M.; Li, W.; Cheng, P. A bimetallic lanthanide metal-organic material as a self-calibrating color-gradient luminescent sensor. Adv. Mater. 2015, 27, 7072–7077. doi: 10.1002/adma.201502760
14. [14]
  Li, Y.; Zhang, S. S.; Song, D. T. A luminescent metal-organic framework as a turn-on sensor for DMF vapor. Angew. Chem. Int. Ed. 2013, 52, 710–713. doi: 10.1002/anie.201207610
15. [15]
  Chen, B. L.; Yang, Y.; Zapata, F.; Lin, G. N.; Qian, G. D.; Lobkovsky, E. B. Luminescent open metal sites within a metal-organic framework for sensing small molecules. Adv. Mater. 2007, 19, 1693–1696. doi: 10.1002/adma.200601838
16. [16]
  Hao, J. N.; Yan, B. Determination of urinary 1-hydroxypyrene for biomonitoring of human exposure to polycyclic aromatic hydrocarbons carcinogens by a lanthanide-functionalized metal-organic framework sensor. Adv. Funct. Mater. 2017, 27, 1603856. doi: 10.1002/adfm.201603856
17. [17]
  Steemers, F. J.; Verboom, W.; Reinhoudt, D. N.; van der Tol, E. B.; Verhoeven, J. W. New sensitizer-modified calyx arenes enabling near-UV excitation of complexed luminescent lanthanide ions. J. Am. Chem. Soc. 1995, 117, 9408–9414. doi: 10.1021/ja00142a004
18. [18]
  Montgomery, C. P.; Murray, B. S.; New, E. J.; Pal, R.; Parker, D. Cell-penetrating metal complex optical probes: targeted and responsive systems based on lanthanide luminescence. Acc. Chem. Res. 2009, 42, 925–937. doi: 10.1021/ar800174z
19. [19]
  Bunzli, J. C. G. Benefiting from the unique properties of lanthanide ions. Acc. Chem. Res. 2006, 39, 53–61. doi: 10.1021/ar0400894
20. [20]
  Yang, X. G.; Lin, X. Q.; Zhao, Y. B.; Zhao, Y. S.; Yan, D. P. Lanthanide metal-organic framework microrods: colored optical waveguides and chiral polarized emission. Angew. Chem. Int. Ed. 2017, 56, 7853–7857. doi: 10.1002/anie.201703917
21. [21]
  Moore, E. G.; Samuel, A. P. S.; Raymond, K. N. From antenna to assay: lessons learned in lanthanide luminescence. Acc. Chem. Res. 2009, 42, 542–552. doi: 10.1021/ar800211j
22. [22]
  Bunzli, J. C.; Piguet, C. Taking advantage of luminescent lanthanide ions. Chem. Soc. Rev. 2005, 34, 1048–1077. doi: 10.1039/b406082m
23. [23]
  Latva, M.; Takalo, H.; Mukkala, V. M.; Matachescu, C.; Rodríguez-Ubis, J. C.; Kankare, J. Correlation between the lowest triplet state energy level of the ligand and lanthanide(Ⅲ) luminescence quantum yield. J. Lumin. 1997, 75, 149–169. doi: 10.1016/S0022-2313(97)00113-0
24. [24]
  Pan, M.; Zhu, Y. X.; Wu, K.; Chen, L.; Hou, Y. J.; Yin, S. Y.; Wang, H. P.; Fan, Y. N.; Su, C. Y. Epitaxial growth of hetero-Ln-MOF hierarchical single crystals for domain-and orientation-controlled multicolor luminescence 3D coding capability. Angew. Chem. Int. Ed. 2017, 56, 14582–14586. doi: 10.1002/anie.201708802
25. [25]
  Lustig, W. P.; Mukherjee, S.; Rudd, N. D.; Desai, A. V.; Li, J.; Ghosh, S. K. Metal-organic frameworks: functional luminescent and photonic materials for sensing applications. Chem. Soc. Rev. 2017, 46, 3242–3285. doi: 10.1039/C6CS00930A
26. [26]
  Hao, J. N.; Xu, X. Y.; Fei, H. H.; Li, L. C.; Yan, B. Functionalization of metal-organic frameworks for photoactive materials. Adv. Mater. 2018, 30, 1705634. doi: 10.1002/adma.201705634
27. [27]
  Zhang, K. Y.; Yu, Q.; Wei, H. J.; Liu, S. J.; Zhao, Q.; Huang, W. Long-lived emissive probes for time-resolved photoluminescence bioimaging and biosensing. Chem. Rev. 2018, 118, 1770–1839 doi: 10.1021/acs.chemrev.7b00425
28. [28]
  Dolgopolova, E. A.; Rice, A. M.; Martin, C. R.; Shustova, N. B. Photochemistry and photophysics of MOFs: steps towards MOF-based sensing enhancements. Chem. Soc. Rev. 2018, 47, 4710–4728. doi: 10.1039/C7CS00861A
29. [29]
  Sheldrick, G. M. SHELXTL NT Version 5.1, Program for Solution and Refinement of Crystal Structures. University of Göttingen: Germany 1997.
30. [30]
  Xia, Y. P.; Li, Y. W.; Li, D. C.; Yao, Q. X.; Du, Y. C.; Dou, J. M. A new Cd (Ⅱ)-based metal-organic framework for highly sensitive fluorescence sensing of nitrobenzene. CrystEngComm. 2015, 17, 2459–2463. doi: 10.1039/C5CE00162E
31. [31]
  Qin, X.; Liu, X. W.; Huang, W.; Bettinelli, M.; Liu, X. G. Lanthanide-activated phosphors based on 4f-5d optical transitions: theoretical and experimental aspects. Chem. Rev. 2017, 117, 4488–4527. doi: 10.1021/acs.chemrev.6b00691
32. [32]
  Kumar, P.; Singh, S.; Gupta, B. K. Future prospects of luminescent nanomaterial based security inks: from synthesis to anti-counterfeiting applications. Nanoscale 2016, 8, 14297–14340 doi: 10.1039/C5NR06965C
33. [33]
  Wang, Z.; Fan, H. T.; Wang, H. F.; Zhao, Q.; Liu, S. J. Dual functional methoxyterephthalic acid terbium complex with luminescence and magnetim. Chin. J. Struct. Chem. 2018, 37, 1349–1355.
34. [34]
  Gu, X. Y.; Jin, C. C.; Cheng, J. W. A series of lanthanide-organic frameworks constructed by Ln₄(OH)₄ clusters and mixed ligands. Chin J. Struct. Chem. 2019, 38, 103–108.
35. [35]
  Zhang, M. B.; Zhang, M. Z.; Chen, X.; Hu, R. X. Syntheses and characterizations of the lanthanide compounds with 4-(4-pyridyl) benzoate and 2, 6-pyridinedicarboxylate as ligands. Chin J. Struct. Chem. 2017, 36, 825–830.
36. [36]
  Su, Q. Q.; Fan, K.; Jin, X. X.; Huang, X. D.; Cheng, S. C.; Luo, L. J.; Li, Y. J.; Xiang, J.; Ko, C. C.; Zheng, L. M.; Lau, T. C. Syntheses, crystal structures and magnetic properties of a series of luminescent lanthanide complexes containing neutral tetradentate phenanthroline-amide ligands. Inorg. Chem. Front. 2019, 6, 1442–1452.
37. [37]
  Yang, W. T.; Tian, H. R.; Li, J. P.; Hui, Y. F.; He, X.; Li, J. Y.; Dang, S.; Xie, Z. G.; Sun, Z. M. Photochromic terbium phosphonates with photomodulated luminescence and metal ion sensitive detection. Chem. Eur. J. 2016, 22, 15451–15457. doi: 10.1002/chem.201602779
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