Citation: Xiao-Dong HUANG, Jiong-Jia CHENG, Cheng-Long TAO, Jian WANG, Xiao-Feng WANG, Gang WU, Guang-Xiang LIU. Barium Complex In Situ Synthesized from 1, 4, 5, 8-Naphthalene Tetracarboxylic Acid: Structure, Detection of Aromatic Amines, and Use as a Precursor of Nano BaCO₃[J]. Chinese Journal of Inorganic Chemistry, ;2022, 38(3): 559-568. doi: 10.11862/CJIC.2022.053 shu

Barium Complex In Situ Synthesized from 1, 4, 5, 8-Naphthalene Tetracarboxylic Acid: Structure, Detection of Aromatic Amines, and Use as a Precursor of Nano BaCO₃

1.
School of Chemistry and Materials Science, Nanjing Normal University, Nanjing 210023, China
2.
College of Environmental Science, Nanjing Xiaozhuang University, Nanjing 211171, China
3.
College of Material and Chemical Engineering, Chuzhou University, Chuzhou, Anhui 239012, China

Corresponding author: Xiao-Feng WANG, wangxf0215@163.com
Received Date: 24 September 2021
Revised Date: 27 December 2021

Figures(14)

Using 1, 4, 5, 8-naphthalene tetracarboxylic acid as a raw material, a luminescent barium-based metalorganic framework (MOF), [Ba(dna)(H₂O)₂]_n (1, H₂dna=1, 8-naphthalic anhydride-4, 5-dicarboxylic), with a 3D topological structure was synthesized by in situ reaction under solvothermal conditions, and characterized by single-crystal X-ray diffraction, elemental analysis, thermogravimetric analysis, and powder X-ray diffraction. The structural analysis demonstrates that it has the underlying 3D topology, encompassing a π-conjugated organic ligand with an anhydride group. It exhibited a low detection limit for aromatic amines in an aqueous solution, which may be driven by an anhydride amine reaction between the ligand and the hosted amines, with a significant enhancement of the emission intensity and visual color change. Furthermore, micro-crystalline BaCO₃ particles can be prepared through direct calcination of complex 1 as a precursor at moderately elevated temperatures.
- Ba(Ⅱ) complex,
- carboxylate group,
- luminescent property,
- BaCO₃ particles
1. [1]
  Merchant Z M, Cheng S G G. Developments in Characterization of Foods Using Antibodies//Gaonkar A G. Characterization of Foods, Emerging Methods. New York: Elsevier Science, 1995: 347-376
2. [2]
  Bao B, Yuwen L L, Zheng X, Weng L, Zhu X, Zhan X, Wang L. A Fluorescent Conjugated Polymer for Trace Detection of Diamines and Biogenic Polyamines[J]. J. Mater. Chem., 2010,20(43):9628-9634. doi: 10.1039/c0jm01467b
3. [3]
  Kaur N, Chopra S, Singh G, Raj P, Bhasin A, Sahoo S K, Kuwar A, Singh N. Chemosensors for Biogenic Amines and Biothiols[J]. J. Mater. Chem. B, 2018,6(30):4872-4902. doi: 10.1039/C8TB00732B
4. [4]
  Medina M Á, Urdiales J L, Rodríguez-Caso C, Ramírez F J, Sanchez-Jiménez F. Biogenic Amines and Polyamines: Similar Biochemistry for Different Physiological Missions and Biomedical Applications[J]. Crit. Rev. Biochem. Mol. Biol., 2003,38(1):23-59. doi: 10.1080/713609209
5. [5]
  Kumpf J, Bunz U H F. Aldehyde-Appended Distyrylbenzenes: Amine Recognition in Water[J]. Chem. Eur. J., 2012,18(29):8921-8924. doi: 10.1002/chem.201200930
6. [6]
  Comes M, Marcos M D, Martinez-Manez R, Sancenon F, Soto J, Villaescusa L A, Amoros P, Beltran D. Chromogenic Discrimination of Primary Aliphatic Amines in Water with Functionalized Mesoporous Silica[J]. Adv. Mater., 2004,16(20):1783-1786. doi: 10.1002/adma.200400143
7. [7]
  Hinoue T, Miyata M, Hisaki I, Tohnai N. Guest-Responsive Fluorescence of Inclusion Crystals with π-Stacked Supramolecular Beads[J]. Angew. Chem. Int. Ed., 2012,51(1):155-158. doi: 10.1002/anie.201106849
8. [8]
  Stetter J R, Penrose W R, Yao S. Sensors, Chemical Sensors, Electrochemical Sensors, and ECS[J]. J. Electrochem. Soc., 2003,150(2):11-16.
9. [9]
  Zhou D Y, Wang Y Y, Jia J, Yu W Z, Qu B F, Li X, Sun X. H-Bonding and Charging Mediated Aggregation and Emission for Fluorescence Turn-On Detection of Hydrazine Hydrate[J]. Chem. Commun., 2015,51(53):10656-10659. doi: 10.1039/C5CC02897C
10. [10]
  Mani P, Ojha A A, Reddy V S, Mandal S. "Turn-On"Fluorescence Sensing and Discriminative Detection of Aliphatic Amines Using a 5-Fold-Interpenetrated Coordination Polymer[J]. Inorg. Chem., 2017,56(12):6772-6775. doi: 10.1021/acs.inorgchem.7b00787
11. [11]
  Yin X M, Gao L L, Li P, Bu R, Sun W J, Gao E Q. Fluorescence Turn-On Response Amplified by Space Confinement in Metal-Organic Frameworks[J]. ACS Appl. Mater. Interfaces, 2019,11(50):47112-47120. doi: 10.1021/acsami.9b18307
12. [12]
  Liu Z Q, HUANG Y Q, SUN W Y. Progress in Fluorescent Recognition and Sensing of Solvent and Small Organic Molecules Based on Metal-Organic Frameworks[J]. Chinese J. Inorg. Chem., 2017,33(11):1959-1969. doi: 10.11862/CJIC.2017.244
13. [13]
  LIU Z, CHEN X, FENG Y L. Two Series of (4, 8)-Connected Lanthanide-Metal Organic Frameworks Based on a Tetra-carboxylate Ligand for Sensing of Small Molecules[J]. Chinese J. Inorg. Chem., 2016,32(8):1413-1420.
14. [14]
  Kreno L E, Leong L E, Farha O K, Allendorf M, Van Duyne R P, Hupp J T. Metal-Organic Framework Materials as Chemical Sensors[J]. Chem. Rev., 2012,112(2):1105-1125. doi: 10.1021/cr200324t
15. [15]
  Yu C X, Chen J, Zhang Y, Song W B, Li X Q, Chen F J, Zhang Y J, Liu D, Liu L L. Highly Efficient and Selective Removal of Anionic Dyes from Aqueous Solution by Using a Protonated Metal-Organic Framework[J]. J. Alloys Compd., 2021,853157383. doi: 10.1016/j.jallcom.2020.157383
16. [16]
  Mallick A, El-Zohry A M, Shekhah O, Yin J, Jia J T, Aggarwal H, Emwas A, Mohammed O F, Eddaoudi M. Unprecedented Ultralow Detection Limit of Amines Using a Thiadiazole-Functionalized Zr(Ⅳ)-Based Metal-Organic Framework[J]. J. Am. Chem. Soc., 2019,141(18):7245-7249. doi: 10.1021/jacs.9b01839
17. [17]
  Hazra A, Bej S, Mondal A, Murmu N C, Banerjee P. Discerning Detection of Mutagenic Biopollutant TNP from Water and Soil Samples with Transition Metal-Containing Luminescence Metal-Organic Frameworks[J]. ACS Omega, 2020,5(26):15949-15961. doi: 10.1021/acsomega.0c01194
18. [18]
  Deng H X, Grunder S, Cordova K E, Valente C, Furukawa H, Hmadeh M, Gandara F, Whalley A C, Liu Z, Asahina S, Kazumori H, O'Keeffe M, Terasaki O, Stoddart J F, Yaghi O M. Large-Pore Apertures in a Series of Metal-Organic Frameworks[J]. Science, 2012,336(6084):1018-1023. doi: 10.1126/science.1220131
19. [19]
  Van-Humbeck J F, McDonald T M, Jing X, Wiers B M, Zhu G, Long J R. Ammonia Capture in Porous Organic Polymers Densely Functionalized with Brønsted Acid Groups[J]. J. Am. Chem. Soc., 2014,136(6):2432-2440. doi: 10.1021/ja4105478
20. [20]
  Marsh C, Han X, Li J N, Lu Z Z, Argent S P, Silva I, Cheng Y Q, Daemen L L, Ramirez-Cuesta A J, Thompson S P, Blake A J, Yang S H, Schröder M. Exceptional Packing Density of Ammonia in a Dual-Functionalized Metal-Organic Framework[J]. J. Am. Chem. Soc., 2021,143(17):6586-6592. doi: 10.1021/jacs.1c01749
21. [21]
  Sun L B, Li Y, Liang Z Q, Yua J H, Xua R R. Structures and Properties of Lanthanide Metal-Organic Frameworks Based on a 1, 2, 3-Triazole-Containing Tetracarboxylate Ligand[J]. Dalton Trans., 2012,41:12790-12796. doi: 10.1039/c2dt31717f
22. [22]
  Fan L M, Fan W L, Li B, Liu X Z, Zhao X, Zhang X T. Structural Diversities and Related Properties of Four Coordination Polymers Synthesized from Original Ligand of 3, 3', 5, 5'-Azobenzenetetracar-boxylic Acid[J]. Dalton Trans., 2015,44:2380-2389. doi: 10.1039/C4DT03076A
23. [23]
  Cui Y J, Yue Y F, Qian G D, Chen B L. Luminescent Functional Metal-Organic Frameworks[J]. Chem. Rev., 2012,112(2):1126-1162. doi: 10.1021/cr200101d
24. [24]
  Wu G, Feng J H, Wang X F. Synthesis, Crystal Structure, and Physical Properties of a Barium(Ⅱ) Benzene-1, 2, 3-tricarboxylic Acid Complex[J]. Z. Anorg. Allg. Chem., 2012,638(6):1047-1052. doi: 10.1002/zaac.201100532
25. [25]
  Wang X F, Yu L, Wei H, Wu G. Synthesis, Crystal Structure, and Physical Properties of a Barium(Ⅱ) p-(Carboxy-l-methyloxy)-benzene-carboxylic Acid Complex[J]. Z. Anorg. Allg. Chem., 2011,637(2):289-292.
26. [26]
  Al-Terkawi A, Scholz G, Emmerling F, Kemnitz E. Barium Coordination Polymers Based on Fluorinated and Fluorine-Free Benzene-Dicarboxylates: Mechanochemical Synthesis and Spectroscopic Characterization[J]. Solid State Sci., 2018,79:99-108. doi: 10.1016/j.solidstatesciences.2018.03.013
27. [27]
  Wu G, Zhang S Q, Guo L. Synthesis, Structure, and Properties of a New Calcium(Ⅱ) Complex of 1, 10-Phenanthroline, 1, 2, 4, 5-Benzene-tetracarboxylic Acid, and a New Precursor to Produce Pure Phase Microcrystalline Calcite Particles[J]. Z. Anorg. Allg. Chem., 2013,639(5):804-809. doi: 10.1002/zaac.201200502
28. [28]
  Thakuria R, Nath N K, Saha B K. The Nature and Applications of π-π Interactions: A Perspective[J]. Cryst. Growth Des., 2019,19(2):523-528. doi: 10.1021/acs.cgd.8b01630
29. [29]
  Xu T, Mohr S, Amende M, Laurin M, Döpper T, Görling A, Libuda J. Benzoic Acid and Phthalic Acid on Atomically Well-Defined MgO (100) Thin Films: Adsorption, Interface Reaction, and Thin Film Growth[J]. J. Phys. Chem. C, 2015,119(48):26968-26979. doi: 10.1021/acs.jpcc.5b07591
30. [30]
  Nyquist R A. Interpreting Infrared, Raman, and Nuclear Magnetic Resonance Spectra: Vol. 1. Elsevier, 2001: 205
31. [31]
  Nakamoto K. Infrared and Raman Spectra of Inorganic and Coordination Compounds, Part B, Applications in Coordination, Organometallic, and Bioinorganic Chemistry. 5th ed. Wiley, 1997: 59-62
32. [32]
  Li Y L, Zhao Y, Wang P, Kang Y S, Liu Q, Zhang X D, Sun W Y. Multifunctional Metal-Organic Frameworks with Fluorescent Sensing and Selective Adsorption Properties[J]. Inorg. Chem., 2016,55(22):11821-11830. doi: 10.1021/acs.inorgchem.6b01869
33. [33]
  Zheng X F, Zhou L, Huang Y M, Wang C G, Duan J G, Wen L L, Tian Z F, Li D F. A Series of Metal-Organic Frameworks Based on 5-(4-Pyridyl)-isophthalic Acid: Selective Sorption and Fluorescence Sensing[J]. J. Mater. Chem. A, 2014,2(31):12413-12422. doi: 10.1039/C4TA01900H
34. [34]
  Xu Y, Tao C L, Yu M X, Xiong Y, Ouyang Y N, Liu X G, Zhao Z J. Tetraphenylethene-Based Luminescent Metal-Organic Framework for Effective Differentiation of cis/trans Isomers[J]. ACS Appl. Mater. Interfaces, 2020,12(31):35266-35272. doi: 10.1021/acsami.0c10702
35. [35]
  Liu C Y, Chen X R, Chen H X, Niu Z, Hirao H, Braunstein P, Lang J P. Ultrafast Luminescent Light-Up Guest Detection Based on the Lock of the Host Molecular Vibration[J]. J. Am. Chem. Soc., 2020,142(14):6690-6697. doi: 10.1021/jacs.0c00368
36. [36]
  Zhang H Y, Nie Y Z, Zhi X M, Du H F, Yang J. Controlled Ring-Opening Polymerization of α-Amino Acid N-Carboxy-anhydride by Frustrated Amine/Borane Lewis Pairs[J]. Chem. Commun., 2017,53(37):5155-5158. doi: 10.1039/C7CC01440F
37. [37]
  Dadkhah M, Salavati-Niasari M, Davar F. A New Inorganic Framework in the Synthesis of Barium Carbonate Nanoparticles via Convenient Solid State Decomposition Route[J]. Adv. Powder Technol., 2013,24(1):14-20. doi: 10.1016/j.apt.2012.01.004
38. [38]
  Tabatabaee M, Kukovec B M, Amjad S, Shishebor M R. Two Different Barium(Ⅱ) 2D Coordination Polymers Constructed with Pyrazine-2, 3-dicarboxylate: Synthesis, Crystal Structures, and Thermal Decomposition to Barium (Ⅱ) Carbonate Nanoparticles[J]. Aust. J. Chem., 2016,69(11):1261-1267. doi: 10.1071/CH16091
1. [1]
  Gaofeng WANG , Shuwen SUN , Yanfei ZHAO , Lixin MENG , Bohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479
2. [2]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
3. [3]
  Yong-Fang Shi , Sheng-Hua Zhou , Zuju Ma , Xin-Tao Wu , Hua Lin , Qi-Long Zhu . From [Ba3S][GeS4] to [Ba3CO3][MS4] (M = Ge, Sn): Enhancing optical anisotropy in IR birefringent crystals via functional group implantation. Chinese Journal of Structural Chemistry, 2025, 44(1): 100455-100455. doi: 10.1016/j.cjsc.2024.100455
4. [4]
  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
5. [5]
  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
6. [6]
  Xiaoling WANG , Hongwu ZHANG , Daofu LIU . Synthesis, structure, and magnetic property of a cobalt(Ⅱ) complex based on pyridyl-substituted imino nitroxide radical. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 407-412. doi: 10.11862/CJIC.20240214
7. [7]
  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
8. [8]
  Tian TIAN , Meng ZHOU , Jiale WEI , Yize LIU , Yifan MO , Yuhan YE , Wenzhi JIA , Bin HE . Ru-doped Co₃O₄/reduced graphene oxide: Preparation and electrocatalytic oxygen evolution property. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 385-394. doi: 10.11862/CJIC.20240298
9. [9]
  Ming ZHENG , Yixiao ZHANG , Jian YANG , Pengfei GUAN , Xiudong LI . Energy storage and photoluminescence properties of Sm³⁺-doped Ba_0.85Ca_0.15Ti_0.90Zr_0.10O₃ lead-free multifunctional ferroelectric ceramics. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 686-692. doi: 10.11862/CJIC.20230388
10. [10]
  Jian Han , Li-Li Zeng , Qin-Yu Fei , Yan-Xiang Ge , Rong-Hui Huang , Fen-Er Chen . Recent advances in remote C(sp³)–H functionalization via chelating group-assisted metal-catalyzed chain-walking reaction. Chinese Chemical Letters, 2024, 35(11): 109647-. doi: 10.1016/j.cclet.2024.109647
11. [11]
  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
12. [12]
  Xin Li , Zhen Xu , Donglei Bu , Jinming Cai , Huamei Chen , Qi Chen , Ting Chen , Fang Cheng , Lifeng Chi , Wenjie Dong , Zhenchao Dong , Shixuan Du , Qitang Fan , Xing Fan , Qiang Fu , Song Gao , Jing Guo , Weijun Guo , Yang He , Shimin Hou , Ying Jiang , Huihui Kong , Baojun Li , Dengyuan Li , Jie Li , Qing Li , Ruoning Li , Shuying Li , Yuxuan Lin , Mengxi Liu , Peinian Liu , Yanyan Liu , Jingtao Lü , Chuanxu Ma , Haoyang Pan , JinLiang Pan , Minghu Pan , Xiaohui Qiu , Ziyong Shen , Qiang Sun , Shijing Tan , Bing Wang , Dong Wang , Li Wang , Lili Wang , Tao Wang , Xiang Wang , Xingyue Wang , Xueyan Wang , Yansong Wang , Yu Wang , Kai Wu , Wei Xu , Na Xue , Linghao Yan , Fan Yang , Zhiyong Yang , Chi Zhang , Xue Zhang , Yang Zhang , Yao Zhang , Xiong Zhou , Junfa Zhu , Yajie Zhang , Feixue Gao , Li Wang . Recent progress on surface chemistry Ⅱ: Property and characterization. Chinese Chemical Letters, 2025, 36(1): 110100-. doi: 10.1016/j.cclet.2024.110100
13. [13]
  Mei Peng , Wei-Min He . Photochemical synthesis and group transfer reactions of azoxy compounds. Chinese Chemical Letters, 2024, 35(8): 109899-. doi: 10.1016/j.cclet.2024.109899
14. [14]
  Wenying Cui , Zhetong Jin , Wentao Fu , Chengshuo Shen . Flag-hinge-like highly luminescent chiral nanographenes with twist geometry. Chinese Chemical Letters, 2024, 35(11): 109667-. doi: 10.1016/j.cclet.2024.109667
15. [15]
  Jie Wu , Xiaoqing Yu , Guoxing Li , Su Chen . Engineering particles towards 3D supraballs-based passive cooling via grafting CDs onto colloidal photonic crystals. Chinese Chemical Letters, 2024, 35(4): 109234-. doi: 10.1016/j.cclet.2023.109234
16. [16]
  Weichen WANG , Chunhua GONG , Junyong ZHANG , Yanfeng BI , Hao XU , Jingli XIE . Construction of two metal-organic frameworks by rigid bis(triazole) and carboxylate mixed-ligands and their catalytic properties for CO₂ cycloaddition reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1377-1386. doi: 10.11862/CJIC.20230415
17. [17]
  Mengfan Zhang , Lingyan Liu , Peng Wei , Wei Feng , Tao Yi . A proximity tagging strategy utilizing an activated aldehyde group as the active site. Chinese Chemical Letters, 2025, 36(4): 110127-. doi: 10.1016/j.cclet.2024.110127
18. [18]
  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
19. [19]
  Chao Liu , Chao Jia , Shi-Xian Gan , Qiao-Yan Qi , Guo-Fang Jiang , Xin Zhao . A luminescent one-dimensional covalent organic framework for organic arsenic sensing in water. Chinese Chemical Letters, 2024, 35(11): 109750-. doi: 10.1016/j.cclet.2024.109750
20. [20]
  Zhijia Zhang , Shihao Sun , Yuefang Chen , Yanhao Wei , Mengmeng Zhang , Chunsheng Li , Yan Sun , Shaofei Zhang , Yong Jiang . Epitaxial growth of Cu_2-xSe on Cu (220) crystal plane as high property anode for sodium storage. Chinese Chemical Letters, 2024, 35(7): 108922-. doi: 10.1016/j.cclet.2023.108922

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(552)
HTML views(116)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Barium Complex In Situ Synthesized from 1, 4, 5, 8-Naphthalene Tetracarboxylic Acid: Structure, Detection of Aromatic Amines, and Use as a Precursor of Nano BaCO3

Metrics

通讯作者: 陈斌, bchen63@163.com

Barium Complex In Situ Synthesized from 1, 4, 5, 8-Naphthalene Tetracarboxylic Acid: Structure, Detection of Aromatic Amines, and Use as a Precursor of Nano BaCO₃