Anthracene-Benzimidazolium Based Fluorescent Chemosensor for Highly Selective Recogniton of H2PO4-

doi:10.11944/j.issn.1000-0518.2020.01.190165

Chinese Journal of Applied Chemistry ›› 2020, Vol. 37 ›› Issue (1): 80-87.DOI: 10.11944/j.issn.1000-0518.2020.01.190165

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Anthracene-Benzimidazolium Based Fluorescent Chemosensor for Highly Selective Recogniton of H₂PO₄^-

DONG Zhiyun,ZHANG Xiaoyu,ZENG Zhengquan,XI Fugui()

Department of Chemistry, Xinzhou Teachers University,Xinzhou,Shanxi 034000,China

Received:2019-06-05 Accepted:2019-09-05 Published:2020-01-08 Online:2020-01-08
Contact: XI Fugui
Supported by:
Supported by the Shanxi “1331 Project” Key Subjects Construction(2019)

Abstract

Abstract:

Two novel anthracene-benzimidazolium based receptors 1 and 2 were synthesized. The anion (F^-, Cl^-, Br^-, I^-, AcO^-, HSO₄^-, H₂PO₄^-, ClO₄^-,NO₃^-) binding properties of receptors 1 and 2 were evaluated in acetonitrile by fluorescence spectroscopy. The receptors 1 and 2 display fluorescent quenching effect with H₂PO₄^-, the quench percentage for receptor 1 is 13%,and for receptor 2 is as much as 94%. The results indicate that receptor 2 is more closely matched to H₂PO₄^- in configuration, and receptor 2 can behave as a “turn-off” fluorescence sensor for H₂PO₄^-. Job-plot shows that receptor 2 and H₂PO₄^- form a 1:1 complex, the binding constant is (3.70±0.16)×10⁴ L/mol, and the detection limit is 3.77×10^-6 mol/L.

Key words: anthracene, benzimidazolium, dihydrogen phosphate, fluorescent chemosensor

DONG Zhiyun, ZHANG Xiaoyu, ZENG Zhengquan, XI Fugui. Anthracene-Benzimidazolium Based Fluorescent Chemosensor for Highly Selective Recogniton of H₂PO₄^-[J]. Chinese Journal of Applied Chemistry, 2020, 37(1): 80-87.

References

[1]	Zhao J,Yang D,Yang X J,et al. Anion Coordination Chemistry:From Recognition to Supramolecular Assembly[J]. Coord Chem Rev,2019,378(8):415-444.
[2]	Yang J,Dong C C,Chen X L,et al. Excimer Disaggregation Enhanced Emission:A Fluorescence “Turn-On” Approach to Oxoanion Recognition[J]. J Am Chem Soc,2019,141(11):4597-4612.
[3]	Tepper R,Schubert U S.Halogen Bonding in Solution:Anion Recognition, Templated Self-assembly, and Organocatalysis[J]. Angew Chem Int Ed,2018,57(21):6004-6016.
[4]	YAN Jijun,KANG Chuanqing,GAO Lianxun.Anion-Naphthalenediimide Interactions and Their Applications[J]. Prog Chem,2018,30(7):902-912(in Chinese). 闫吉军,康传清,高连勋. 阴离子-萘四酸双酰亚胺相互作用及其应用[J]. 化学进展,2018,30(7):902-912.
[5]	Nieto S,Hargrove A E,Zhang T,et al. Artificial Receptors for the Recognition of Phosphorylated Molecules[J]. Chem Rev,2011,111(11):6603-6782.
[6]	Warwick C,Guerreiro A,Soares A.Sensing and Analysis of Soluble Phosphates in Environmental Samples:A Review[J]. Biosens Bioelectron,2012,41(1):1-11.
[7]	Law A A T,Adeloju S B. Progress and Recent Advances in Phosphate Sensors:A Review[J]. Talanta,2013,114:191-203.
[8]	Zhang D,Cochrane J R,Martinez A,et al. Recent Advances in H2PO4-Fluorescent Sensors[J]. RSC Adv,2014,4(56):29735-29749.
[9]	Patra C,Bhanja A K,Sen C,et al. Imine-Functionalized Thioether Zn(Ⅱ) Turn-On Fluorescent Sensor and Its Selective Sequential Logic Operations with H2PO4-, DFT Computation and Live Cell Imaging[J]. RSC Adv,2016,6(58):53378-53388.
[10]	Ghosh K,Saha I.Ortho-Phenylenediamine-Based Open and Macrocyclic Receptors in Selective Sensing of H2PO4-, ATP and ADP under Different Conditions[J]. Org Biomol Chem,2012,10(47):9383-9392.
[11]	Kondo S I,Takai R.Selective Detection of Dihydrogen Phosphate Anion by Fluorescence Change with Tetraamide-Based Receptors Bearing Isoquinolyl and Quinolyl Moieties[J]. Org Lett,2013,15(3):538-541.
[12]	Kumar A,Kumar V,Upadhyay K K.An Al3+ and H2PO4-/HSO4- Selective Conformational Arrest and Bail to a Pyrimidine-Naphthalene Anchored Molecular Switch[J]. Analyst,2013,138(6):1891-1897.
[13]	Kui D,Niu S Z,Li Q,et al. A Highly Selective Ratiometric Fluorescent Probe for the Cascade Detection of Zn2+ and H2PO4- and Its Application in Living Cell Imaging[J]. RSC Adv,2017,7(64):40615-40620.
[14]	Du K,Liu J,Shen R,et al. Design and Synthesis of a New Fluorescent Probe for Cascade Detection of Zn2+ and H2PO4- in Water and Targeted Imaging of Living Cells[J]. Luminescence,2019,34(4):407-414.
[15]	Zhang Y H,Huang H W,Yang S S,et al. A New Ferrocenophane with Amide and Triazole Donors for Recognition of Dihydrogenphosphate Anion[J]. J Organomet Chem,2018,871:74-78.
[16]	Du K,Niu S,Chen X,et al. A Novel Highly Selective Ratiometric Fluorescent Sensor for Relay Recognition of Zn2+ and H2PO4-[J]. Tetrahedron Lett,2018,59(4):356-360.
[17]	Zhang Y M,Li Y F,Zhong K P,et al. A Novel Pillar[5]arene-Based Supramolecular Organic Framework Gel to Achieve an Ultrasensitive Response by Introducing the Competition of Cation…π and π…π Interactions[J]. Soft Matter,2018,14:3624-3631.
[18]	Feng X,Fu Y,Jin J,et al. A Highly Selective and Sensitive Fluorescent Sensor for Relay Recognition of Zn2+ and HSO4-/H2PO4- Fluorescent Responses[J]. Anal Biochem,2018,563:20-24.
[19]	Du W,Jia C,Zhang Y,et al. A Sc-3-HF Complex as a Fluorescent Chemosensor for the Selective Detection of Dihydrogen Phosphate[J]. Anal Methods,2018,10:1993-1998.
[20]	Das R,Pathak N,Choudhury S,et al. Dihydrogenphosphate Recognition:Assistance from the Acidic OH Moiety of the Anion[J]. J Mol Struct,2017,1148:81-88.
[21]	Su Y,Zhang D,Jia P,et al. Highly Selective and Sensitive Long Fluorescence Lifetime Polyurethane Foam Sensor Based on Tb-Complex as Chromophore for the Detection of H2PO4- in Water[J]. Spectrochim Acta A,2019,217:86-92.
[22]	Wang K P,Zhang S J,Lv C D,et al. A Highly Sensitive and Selective Turn-On Fluorescent Sensor for Dihydrogen Phosphate in Living Cells[J]. Sens Actuators B:Chem,2017,247:791-796.
[23]	Molina P,Zapata F,Caballero A.Anion Recognition Strategies Based on Combined Noncovalent Interactions[J]. Chem Rev,2017,117(15):9907-9972.
[24]	Liu Q X,Hu Z L,Zhao Z X.A New Fluorescent-Colorimetric Chemosensor for Fluoride Anion Based on Benzimidazolium Salt[J]. Tetrahedron,2018,74(46):6710-6716.
[25]	Kim J,Morozumi T,Nakamura H.Control Between TICT and PET Using Chemical Modification of N-Phenyl-9-anthracenecarboxamide and Its Application to a Crown Ether Type Chemosensor[J]. Tetrahedron,2008,64(47):10735-10740.
[26]	Zhou L,Sun Q F.A Self-assembled Pd2L4 Cage that Selectively Encapsulates Nitrate[J]. Chem Commun,2015,51(94):16767-16770.
[27]	Herbert J M,Woodgate P D,Denny W A. Potential Antitumor Agents.53.Synthesis, DNA Binding Properties, and Biological Activity of Perimidines Designed as Minimal DNA-Intercalating Agents[J]. J Med Chem,1987,30(11):2081-2086.
[28]	Liu G,Zhao L.A Simple Colorimetric and On-Off Fluorescent Chemosensor for Biologically Important Anions Based on Thiourea Groups[J]. Spectrosc Lett,2012,45(6):424-429.
[29]	HUANG Xiaomei,DENG Xiang.Preparation of New Photoluminescent Carbon Dots and Its Application in Hg2+ Detection[J]. Chinese J Appl Chem,2019,36(5):603-610(in Chinese). 黄小梅,邓祥. 新型荧光碳点的制备及其在Hg2+检测中的应用[J]. 应用化学,2019,36(5):603-610.
[30]	Valeur B,Pouget J,Bourson J.Tuning of Photoinduced Energy Transfer in a Bichromophoric Coumarin Supermolecule by Cation Binding[J]. J Phys Chem,1992,96:6545-6549.
[31]	Zapata F,Gonzalez L,Caballero A,et al. Dual Role of the 1,2,3-Triazolium Ring as a Hydrogen-Bond Donor and Anion-π Receptor in Anion-Recognition Processes[J]. Chem-Eur J,2015,21(27):9797-9808.

Anthracene-Benzimidazolium Based Fluorescent Chemosensor for Highly Selective Recogniton of H₂PO₄^-

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