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
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通讯作者: 陈斌, bchen63@163.com

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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

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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