A novel multiemissive Ln/covalent-organic frameworks for ratiometric detection of 2,6-dipicolinic acid

다국어 초록 (Multilingual Abstract)

As one of the specific biomarkers of anthrax, timely, sensitive and accurate detection of 2,6-dipicolinicacid (DPA) plays an important role in preventing biological weapons attacks and disease outbreaks.
Here, multiemission Eu3+/covalent- organic framework (COFDTA-TFP) and Tb3+/COFDTA-TFP were constructedby the coordination between Eu3+ or Tb3+ with fluorescent COFDTA-TFP which was prepared byamine-aldehyde dehydration condensation between 2,5-diaminoterephthalic acid and 2,4,6-triformylphloroglucinol for the first time. The Eu3+/COFDTA-TFP and Tb3+/COFDTA-TFP can emit nonoverlappingfluorescence of COFDTA-TFP and Eu3+ or Tb3+, which was used to ratiometric detection ofDPA. Due to the strong coordination between the nitrogen atoms in the pyridine ring and the oxygenatoms in the carboxyl group of DPA with Eu3+ or Tb3+, DPA replaced coordinated H2O to sensitize fluorescenceof Eu3+ or Tb3+ by ‘‘antenna” effect but fluorescence of COFDTA-TFP with two-dimensional lamellarstructure was kept constant as a reference. The linear range and detection limit of ratiometric fluorescencesensor based on Eu3+/COFDTA-TFP for detection of DPA are 0.01–12 mM and 4.2 nM, respectively.
The linear range and detection limit of ratiometric fluorescence sensor based on Tb3+/COFDTA-TFP fordetection of DPA are 0.01–9.0 mM and 2.9 nM, respectively.

참고문헌 (Reference)

1 A.P Dementjev, "X-Ray photoelectron spectroscopy reference data for identification of the C3N4 phase in carbon–nitrogen films" Elsevier BV 9 (9): 1904-1907, 2000

2 Xiaoliang Zeng, "Visual Detection of Fluoride Anions Using Mixed Lanthanide Metal–Organic Frameworks with a Smartphone" American Chemical Society (ACS) 92 (92): 2097-2102, 2019

3 Xiuna Mi, "Tunable Light Emission and Multiresponsive Luminescent Sensitivities in Aqueous Solutions of Two Series of Lanthanide Metal–Organic Frameworks Based on Structurally Related Ligands" American Chemical Society (ACS) 11 (11): 7914-7926, 2019

4 Chidharth Krishnaraj, "Triggering White-Light Emission in a 2D Imine Covalent Organic Framework Through Lanthanide Augmentation" American Chemical Society (ACS) 11 (11): 27343-27352, 2019

5 Lu Liu, "Triazine-cored covalent organic framework for ultrasensitive detection of polybrominated diphenyl ethers from real samples: Experimental and DFT study" Elsevier BV 403 : 123917-, 2021

6 Lan Guo, "The role of l-histidine as molecular tongs: a strategy of grasping Tb³⁺ using ZIF-8 to design sensors for monitoring an anthrax biomarker on-the-spot" Royal Society of Chemistry (RSC) 11 (11): 2407-2413, 2020

7 Christian S. Diercks, "The atom, the molecule, and the covalent organic framework" American Association for the Advancement of Science (AAAS) 355 (355): 2017

8 Lina Zhang, "Terbium Functionalized Schizochytrium-Derived Carbon Dots for Ratiometric Fluorescence Determination of the Anthrax Biomarker" MDPI AG 9 (9): 1234-, 2019

9 Ke Luan, "Terbium Functionalized Micelle Nanoprobe for Ratiometric Fluorescence Detection of Anthrax Spore Biomarker" American Chemical Society (ACS) 90 (90): 3600-3607, 2018

10 Mohaddeseh Afshari, "Synthesis of new imine-linked covalent organic framework as high efficient absorbent and monitoring the removal of direct fast scarlet 4BS textile dye based on mobile phone colorimetric platform" Elsevier BV 385 : 121514-, 2020

11 Illariia A. Razumkova ; Alexander E. Sedykh ; Yuriy G. Denisenko ; Klaus Müller-Buschbaum, "Synthesis and luminescence properties of β-NaRE0.95Eu0.05F4 (RE¼Y, Lu)" 한국공업화학회 92 : 218-225, 2020

12 Hua-Qing Yin, "Strong dual emission in covalent organic frameworks induced by ESIPT" Royal Society of Chemistry (RSC) 10 (10): 11103-11109, 2019

13 Guogang Li, "Single-Composition Trichromatic White-Emitting Ca₄Y₆(SiO₄)₆O: Ce³⁺/Mn²⁺/Tb³⁺Phosphor: Luminescence and Energy Transfer" American Chemical Society (ACS) 4 (4): 296-305, 2011

14 Han Wang, "Recent progress in covalent organic framework thin films: fabrications, applications and perspectives" Royal Society of Chemistry (RSC) 48 (48): 488-516, 2019

15 Long Yu, "Rational Design of Dual-Emission Lanthanide Metal–Organic Framework for Visual Alkaline Phosphatase Activity Assay" American Chemical Society (ACS) 13 (13): 11646-11656, 2021

16 Mingcong Rong, "Ratiometric fluorometric determination of the anthrax biomarker 2,6-dipicolinic acid by using europium(III)-doped carbon dots in a test stripe" Springer Science and Business Media LLC 185 (185): 201-, 2018

17 Linli Hou, "Ratiometric fluorescence detection of dipicolinic acid based on Microporous Ln/melamine-terephthaladehyde schiff base networks complex" Elsevier BV 209 : 120534-, 2020

18 Wei Liu, "Ratiometric Monitoring of Thorium Contamination in Natural Water Using a Dual-Emission Luminescent Europium Organic Framework" American Chemical Society (ACS) 53 (53): 332-341, 2018

19 Fei Li, "Pd loaded and covalent-organic framework involved chitosan aerogels and their application for continuous flow-through aqueous CB decontamination" Royal Society of Chemistry (RSC) 6 (6): 11140-11146, 2018

20 Dadong Shao, "PANI/GO as a super adsorbent for the selective adsorption of uranium(VI)" Elsevier BV 255 : 604-612, 2014

21 Emerson H. de Faria, "New Highly Luminescent Hybrid Materials: Terbium Pyridine−Picolinate Covalently Grafted on Kaolinite" American Chemical Society (ACS) 3 (3): 1311-1318, 2011

22 Jie-Yu Yue, "Metal ion-assisted carboxyl-containing covalent organic frameworks for the efficient removal of Congo red" Royal Society of Chemistry (RSC) 48 (48): 17763-17769, 2019

23 Yang Yu, "Luminescent humidity sensors based on porous Ln3+-MOFs" Royal Society of Chemistry (RSC) 14 (14): 7157-, 2012

24 Osman Altunbas, "Luminescent detection of Ochratoxin A using terbium chelated mesoporous silica nanoparticles" Elsevier BV 382 : 121049-, 2020

25 Anna M. Kaczmarek, "Luminescent Ratiometric Thermometers Based on a 4f–3d Grafted Covalent Organic Framework to Locally Measure Temperature Gradients During Catalytic Reactions" Wiley 60 (60): 3727-3736, 2020

26 Yan-Ning Wang, "Ln-CPs constructed from unsymmetrical tetracarboxylic acid ligand: Tunable white-light emission and highly sensitive detection of CrO42−, Cr2O72−, MnO4− in water" Elsevier BV 229 : 117915-, 2020

27 Yin Tian, "Ligand-exchange mechanism: new insight into solid-phase extraction of uranium based on a combined experimental and theoretical study" Royal Society of Chemistry (RSC) 17 (17): 7214-7223, 2015

28 Ahmad Abdallah, "Lanthanide-Based Coordination Polymers With 1,4-Carboxyphenylboronic Ligand: Multiemissive Compounds for Multisensitive Luminescent Thermometric Probes" American Chemical Society (ACS) 58 (58): 462-475, 2018

29 Sven Arenz, "Intense near-infrared luminescence of anhydrous lanthanide(III) iodides in an imidazolium ionic liquid" Elsevier BV 402 (402): 75-79, 2005

30 Brian J. Smith, "Insight into the crystallization of amorphous imine-linked polymer networks to 2D covalent organic frameworks" Royal Society of Chemistry (RSC) 52 (52): 3690-3693, 2016

31 Tiancheng Sun, "In situ self-assembled cationic lanthanide metal organic framework membrane sensor for effective MnO4− and ascorbic acid detection" Elsevier BV 1142 : 211-220, 2021

32 Sasanka Dalapati, "Highly Emissive Covalent Organic Frameworks" American Chemical Society (ACS) 138 (138): 5797-5800, 2016

33 Han Wang, "High capacitance of dipicolinic acid-intercalated MXene in neutral water-based electrolyte" Elsevier BV 399 : 125850-, 2020

34 Yuan-Jun Tong, "Graphene Oxide-Supported Lanthanide Metal–Organic Frameworks with Boosted Stabilities and Detection Sensitivities" American Chemical Society (ACS) 92 (92): 15550-15557, 2020

35 Li Yang, "Fluorescent core-shell SiO2@vertical covalent organic frameworks nanosheets for sensing application" Elsevier BV 341 : 129995-, 2021

36 Guoyan Zhang, "Fluorescent and colorimetric determination of glutathione based on the inner filter effect between silica nanoparticle–gold nanocluster nanocomposites and oxidized 3,3′,5,5′-tetramethylbenzidine" Royal Society of Chemistry (RSC) 145 (145): 6254-6261, 2020

37 Rongke Gao, "Fast and sensitive detection of an anthrax biomarker using SERS-based solenoid microfluidic sensor" Elsevier BV 72 : 230-236, 2015

38 Seung-Tae Yang, "Facile synthesis of covalent organic frameworks COF-1 and COF-5 by sonochemical method" Royal Society of Chemistry (RSC) 2 (2): 10179-, 2012

39 Kristijan Krekić, "Facile access to efficiently luminescent Ln³⁺ phosphonic ester coordination polymers (Ln = Eu, Tb, Dy)" Royal Society of Chemistry (RSC) 53 (53): 11076-11079, 2017

40 Kai Xing, "Europium-Functionalized Flexible Luminescent Zeolite-like Supramolecular Assembly for Ratiometric Anthrax Biomarker Determination" American Chemical Society (ACS) 11 (11): 36081-36089, 2019

41 Hongyu Zuo, "Europium Ionic Liquid Grafted Covalent Organic Framework with Dual Luminescence Emissions as Sensitive and Selective Acetone Sensor" American Chemical Society (ACS) 11 (11): 39201-39208, 2019

42 M. Deniz Yilmaz, "Eriochrome Black T–Eu³⁺ Complex as a Ratiometric Colorimetric and Fluorescent Probe for the Detection of Dipicolinic Acid, a Biomarker of Bacterial Spores" American Chemical Society (ACS) 90 (90): 4221-4225, 2018

43 Xun Feng, "Enhanced luminescence and tunable magnetic properties of lanthanide coordination polymers based on fluorine substitution and phenanthroline ligand" Royal Society of Chemistry (RSC) 9 (9): 16328-16338, 2019

44 Qingqing Tan, "Embedding carbon dots and gold nanoclusters in metal-organic frameworks for ratiometric fluorescence detection of Cu2+" Springer Science and Business Media LLC 412 (412): 1317-1324, 2020

45 Yang Deng, "Embedding Ultrasmall Au Clusters into the Pores of a Covalent Organic Framework for Enhanced Photostability and Photocatalytic Performance" Wiley 59 (59): 6082-6089, 2020

46 Qi-Xian Wang, "Dual lanthanide-doped complexes: the development of a time-resolved ratiometric fluorescent probe for anthrax biomarker and a paper-based visual sensor" Elsevier BV 94 : 388-393, 2017

47 Yonghai Song, "Dual emission N-doped carbon dot@benzotrithiophene tricarbaldehyde-terephthalic dihydrazide covalent organic framework" Royal Society of Chemistry (RSC) 56 (56): 14913-14916, 2020

48 Pradip Pachfule, "Diacetylene Functionalized Covalent Organic Framework (COF) for Photocatalytic Hydrogen Generation" American Chemical Society (ACS) 140 (140): 1423-1427, 2018

49 Francesca Buiarelli, "Determination of the main bioaerosol components using chemical markers by liquid chromatography–tandem mass spectrometry" Elsevier BV 149 : 103974-, 2019

50 Royston Goodacre, "Detection of the Dipicolinic Acid Biomarker in Bacillus Spores Using Curie-Point Pyrolysis Mass Spectrometry and Fourier Transform Infrared Spectroscopy" American Chemical Society (ACS) 72 (72): 119-127, 1999

51 Lulu Guo, "Covalent organic frameworks for fluorescent sensing: Recent developments and future challenges" Elsevier BV 440 : 213957-, 2021

52 Rui Ai, "Covalent organic framework-inspired chromogenic system for visual colorimetric detection of carcinogenic 3, 3′-diaminobenzidine" Elsevier BV 304 : 127372-, 2020

53 Steven J. Lyle, "Covalent Organic Frameworks: Organic Chemistry Extended into Two and Three Dimensions" Elsevier BV 1 (1): 172-184, 2019

54 Ryuhei Nishiyabu, "Confining Molecules within Aqueous Coordination Nanoparticles by Adaptive Molecular Self-Assembly" Wiley 48 (48): 9465-9468, 2009

55 Zhong-Rui Yang, "Boric-Acid-Functional Lanthanide Metal–Organic Frameworks for Selective Ratiometric Fluorescence Detection of Fluoride Ions" American Chemical Society (ACS) 89 (89): 1930-1936, 2017

56 Morgan L. Cable, "Bacterial Spore Detection by [Tb³⁺(macrocycle)(dipicolinate)] Luminescence" American Chemical Society (ACS) 129 (129): 1474-1475, 2007

57 Meng Li Liu, "Anthrax biomarker: An ultrasensitive fluorescent ratiometry of dipicolinic acid by using terbium(III)-modified carbon dots" Elsevier BV 191 : 443-448, 2019

58 Lars Grunenberg, "Amine-Linked Covalent Organic Frameworks as a Platform for Postsynthetic Structure Interconversion and Pore-Wall Modification" American Chemical Society (ACS) 143 (143): 3430-3438, 2021

59 Miao Xu, "Alizarin Red–Tb³⁺ complex as a ratiometric colorimetric and fluorescent dual probe for the smartphone-based detection of an anthrax biomarker" Royal Society of Chemistry (RSC) 11 (11): 4267-4273, 2019

60 Zhengde Li ; Zhiying Zhan ; Yuejiao Jia ; Zhang Li ; Ming Hu, "A water-stable europium-MOF as a multifunctional luminescent sensor for some inorganic ions and dichloromethane molecule" 한국공업화학회 97 : 180-187, 2021

61 Ziyu Gan, "A dual-emission fluorescence sensor for ultrasensitive sensing mercury in milk based on carbon quantum dots modified with europium (III) complexes" Elsevier BV 328 : 128997-, 2021

62 Mingcong Rong, "A Label-Free Fluorescence Sensing Approach for Selective and Sensitive Detection of 2,4,6-Trinitrophenol (TNP) in Aqueous Solution Using Graphitic Carbon Nitride Nanosheets" American Chemical Society (ACS) 87 (87): 1288-1296, 2014

63 Hongwei Yang, "A Eu3+-inspired fluorescent carbon nanodot probe for the sensitive visualization of anthrax biomarker by integrating EDTA chelation" Elsevier BV 208 : 120368-, 2020

64 Hao Wang, "A Boric Acid-Functionalized Lanthanide Metal–Organic Framework as a Fluorescence “Turn-on” Probe for Selective Monitoring of Hg²⁺ and CH₃Hg⁺" American Chemical Society (ACS) 92 (92): 3366-3372, 2020