Syntheses, Structures and Photoluminescence of Novel Lanthanide-organic Frameworks Based on 1, 4-Bis(3, 5-dicarboxylic pyrazol-1-ylmethyl) Benzene
- Corresponding author: Yong-Ke HE, yk-h@163.com Ya-Guang SUN, sunyaguang@syuct.edu.cn
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
Li, J. R.; Sculley, J.; Zhou, H. C. Metal-organic frameworks for separations. Chem. Rev. 2012, 112, 869–932.
doi: 10.1021/cr200190s
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
Bunzli, J. C. G. Benefiting from the unique properties of lanthanide ions. Acc. Chem. Res. 2006, 39, 53–61.
doi: 10.1021/ar0400894
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
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
Bunzli, J. C.; Piguet, C. Taking advantage of luminescent lanthanide ions. Chem. Soc. Rev. 2005, 34, 1048–1077.
doi: 10.1039/b406082m
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
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
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
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
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
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
Sheldrick, G. M. SHELXTL NT Version 5.1, Program for Solution and Refinement of Crystal Structures. University of Göttingen: Germany 1997.
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
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
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
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.
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.
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.
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.
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
Jiakun Bai , Junhui Jia , Aisen Li . An elastic organic crystal with piezochromic luminescent behavior. Chinese Journal of Structural Chemistry, 2024, 43(6): 100323-100323. doi: 10.1016/j.cjsc.2024.100323
Ruikui YAN , Xiaoli CHEN , Miao CAI , Jing REN , Huali CUI , Hua YANG , Jijiang WANG . Design, synthesis, and fluorescence sensing performance of highly sensitive and multi-response lanthanide metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 834-848. doi: 10.11862/CJIC.20230301
Min Chen , Boyu Peng , Xuyun Guo , Ye Zhu , Hanying Li . Polyethylene interfacial dielectric layer for organic semiconductor single crystal based field-effect transistors. Chinese Chemical Letters, 2024, 35(4): 109051-. doi: 10.1016/j.cclet.2023.109051
Jaeyong Ahn , Zhenping Li , Zhiwei Wang , Ke Gao , Huagui Zhuo , Wanuk Choi , Gang Chang , Xiaobo Shang , Joon Hak Oh . Surface doping effect on the optoelectronic performance of 2D organic crystals based on cyano-substituted perylene diimides. Chinese Chemical Letters, 2024, 35(9): 109777-. doi: 10.1016/j.cclet.2024.109777
Lei Wang , Jun-Jie Wu , Chang-Cun Yan , Wan-Ying Yang , Zong-Lu Che , Xin-Yu Xia , Xue-Dong Wang , Liang-Sheng Liao . Near-infrared organic lasers with ultra-broad emission bands by simultaneously harnessing four-level and six-level systems. Chinese Chemical Letters, 2024, 35(8): 109365-. doi: 10.1016/j.cclet.2023.109365
Tiankai Sun , Hui Min , Zongsu Han , Liang Wang , Peng Cheng , Wei Shi . Rapid detection of nanoplastic particles by a luminescent Tb-based coordination polymer. Chinese Chemical Letters, 2024, 35(5): 108718-. doi: 10.1016/j.cclet.2023.108718
Lihua Ma , Song Guo , Zhi-Ming Zhang , Jin-Zhong Wang , Tong-Bu Lu , Xian-Shun Zeng . Sensitizing photoactive metal–organic frameworks via chromophore for significantly boosting photosynthesis. Chinese Chemical Letters, 2024, 35(5): 108661-. doi: 10.1016/j.cclet.2023.108661
Xiaoyan Peng , Xuanhao Wu , Fan Yang , Yefei Tian , Mingming Zhang , Hongye Yuan . Gas sensors based on metal-organic frameworks: challenges and opportunities. Chinese Journal of Structural Chemistry, 2024, 43(3): 100251-100251. doi: 10.1016/j.cjsc.2024.100251
Deshuai Zhen , Chunlin Liu , Qiuhui Deng , Shaoqi Zhang , Ningman Yuan , Le Li , Yu Liu . A review of covalent organic frameworks for metal ion fluorescence sensing. Chinese Chemical Letters, 2024, 35(8): 109249-. doi: 10.1016/j.cclet.2023.109249
Yunyu Zhao , Chuntao Yang , Yingjian Yu . A review on covalent organic frameworks for rechargeable zinc-ion batteries. Chinese Chemical Letters, 2024, 35(7): 108865-. doi: 10.1016/j.cclet.2023.108865
Hong Dong , Feng-Ming Zhang . Covalent organic frameworks for artificial photosynthetic diluted CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(7): 100307-100307. doi: 10.1016/j.cjsc.2024.100307
Kang Wang , Qinglin Zhou , Weijin Li . Conductive metal-organic frameworks for electromagnetic wave absorption. Chinese Journal of Structural Chemistry, 2024, 43(10): 100325-100325. doi: 10.1016/j.cjsc.2024.100325
Yinyin Xu , Yuanyuan Li , Jingbo Feng , Chen Wang , Yan Zhang , Yukun Wang , Xiuwen Cheng . Covalent organic frameworks doped with manganese-metal organic framework for peroxymonosulfate activation. Chinese Chemical Letters, 2024, 35(4): 108838-. doi: 10.1016/j.cclet.2023.108838
Xinyi Cao , Yucheng Jin , Hailong Wang , Xu Ding , Xiaolin Liu , Baoqiu Yu , Xiaoning Zhan , Jianzhuang Jiang . A tetraaldehyde-derived porous organic cage and covalent organic frameworks: Syntheses, structures, and iodine vapor capture. Chinese Chemical Letters, 2024, 35(9): 109201-. doi: 10.1016/j.cclet.2023.109201
Jing-Jing Zhang , Lujun Lou , Rui Lv , Jiahui Chen , Yinlong Li , Guangwei Wu , Lingchao Cai , Steven H. Liang , Zhen Chen . Recent advances in photochemistry for positron emission tomography imaging. Chinese Chemical Letters, 2024, 35(8): 109342-. doi: 10.1016/j.cclet.2023.109342
Hongdao LI , Shengjian ZHANG , Hongmei DONG . Magnetic relaxation and luminescent behavior in nitronyl nitroxide-based annuluses of rare-earth ions. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 972-978. doi: 10.11862/CJIC.20230411
Zhixue Liu , Haiqi Chen , Lijuan Guo , Xinyao Sun , Zhi-Yuan Zhang , Junyi Chen , Ming Dong , Chunju Li . Luminescent terphen[3]arene sulfate-activated FRET assemblies for cell imaging. Chinese Chemical Letters, 2024, 35(9): 109666-. doi: 10.1016/j.cclet.2024.109666
Yue Mao , Zhonghang Chen , Tiankai Sun , Wenyue Cui , Peng Cheng , Wei Shi . Luminescent coordination polymers with mixed carboxylate and triazole ligands for rapid detection of chloroprene metabolite. Chinese Journal of Structural Chemistry, 2024, 43(9): 100353-100353. doi: 10.1016/j.cjsc.2024.100353
Jian Yang , Guang Yang , Zhijie Chen . Capturing carbon dioxide from air by using amine-functionalized metal-organic frameworks. Chinese Journal of Structural Chemistry, 2024, 43(5): 100267-100267. doi: 10.1016/j.cjsc.2024.100267
Zhiqiang Liu , Qiang Gao , Wei Shen , Meifeng Xu , Yunxin Li , Weilin Hou , Hai-Wei Shi , Yaozuo Yuan , Erwin Adams , Hian Kee Lee , Sheng Tang . Removal and fluorescence detection of antibiotics from wastewater by layered double oxides/metal-organic frameworks with different topological configurations. Chinese Chemical Letters, 2024, 35(8): 109338-. doi: 10.1016/j.cclet.2023.109338