Study on novel biphenyl chalcone scaffolds: A dual spectroscopic approach for efficient sensing of hydrazine with low concentration

Paresh Narayan Patel; Shivani Nagindas Tandel; Amar Ghanshyam Deshmukh; Preksha Basant Patel

doi:10.5155/eurjchem.14.2.264-272.2380

PDF

Published: Jun 30, 2023

DOI: https://doi.org/10.5155/eurjchem.14.2.264-272.2380

Keywords:

Sensor, Pyrazole, Chalcone, Biphenyl, Hydrazine, Fluorescent

Section

Research Article

Issue

Vol. 14 No. 2 (2023): June 2023

Dates

Received 2022-12-10
Accepted 2023-03-11
Published 2023-06-30

Paresh Narayan Patel

Laboratory of Bio-Organic Chemistry, Tarsadia Institute of Chemical Science (TICS), Uka Tarsadia University, Bardoli - 394 350, Gujarat, India

https://orcid.org/0000-0002-8514-4753

Shivani Nagindas Tandel

Laboratory of Bio-Organic Chemistry, Tarsadia Institute of Chemical Science (TICS), Uka Tarsadia University, Bardoli - 394 350, Gujarat, India

https://orcid.org/0000-0002-3533-2545

Amar Ghanshyam Deshmukh

Laboratory of Bio-Organic Chemistry, Tarsadia Institute of Chemical Science (TICS), Uka Tarsadia University, Bardoli - 394 350, Gujarat, India

https://orcid.org/0000-0002-9851-8953

Preksha Basant Patel

Laboratory of Bio-Organic Chemistry, Tarsadia Institute of Chemical Science (TICS), Uka Tarsadia University, Bardoli - 394 350, Gujarat, India

https://orcid.org/0000-0001-5451-7281

Abstract

Hydrazine and its derivatives, as harmful substances, seriously risk the health of humans and the environment. On the basis of the admirable luminescent properties and low biological harmfulness of the biphenyl moiety, a biphenyl moiety can be combined with a naphthalene ring via the chalcone scaffold easily traced by a nucleophilic group. Therefore, biphenyl chalcones (BPCs) decorated with various naphthalene systems as fluorescent sensors for hydrazine are synthesised by Claisen-Schmidt condensation. The present work describes the comparative studies of two different protocols for the synthesis of three different BPCs. The structures of all novel BPCs were investigated by FT-IR, NMR, and HRMS spectroscopy. These BPCs show a red shift with a fluorescent peak and an enhancement in intensity with increasing solvent polarity from hexane to methanol. Methanol shows strong fluorescence emission; therefore, methanol is used as the solvent in hydrazine sensing experiments. The BPCs display fluorescent variation from yellow to blue fluorescence after binding with hydrazine. These BPCs sensors are able to identify hydrazine in a fast response rate and 5 min response time. The screening study of hydrazine in various soil samples by prepared BPCs is highly efficient. A study of the pH dependence of these probes shows excellent sensitivity in the pH range of 5 to 10.

This Abstract was viewed 606 times |

Article PDF downloaded 349 times

How to Cite

(1)

Patel, P. N.; Tandel, S. N.; Deshmukh, A. G.; Patel, P. B. Study on Novel Biphenyl Chalcone Scaffolds: A Dual Spectroscopic Approach for Efficient Sensing of Hydrazine With Low Concentration. Eur. J. Chem. 2023, 14, 264-272.

Links for Article

Crossref - Scopus - Google - European PMC

References

[1]. Nguyen, K. H.; Hao, Y.; Chen, W.; Zhang, Y.; Xu, M.; Yang, M.; Liu, Y.-N. Recent progress in the development of fluorescent probes for hydrazine. Luminescence 2018, 33, 816-836.
https://doi.org/10.1002/bio.3505

[2]. Zelnick, S. D.; Mattie, D. R.; Stepaniak, P. C. Occupational exposure to hydrazines: treatment of acute central nervous system toxicity. Aviat. Space Environ. Med. 2003, 74, 1285-1291.

[3]. Troyan, J. E. Properties, production, and uses of hydrazine. Ind. Eng. Chem. 1953, 45, 2608-2612.
https://doi.org/10.1021/ie50528a020

[4]. Dambrauskas, T.; Cornish, H. H. The distribution, metabolism, and excretion of hydrazine in rat and mouse. Toxicol. Appl. Pharmacol. 1964, 6, 653-663.
https://doi.org/10.1016/0041-008X(64)90115-2

[5]. Davis, S. M.; Yilmaz, N. Advances in hypergolic propellants: Ignition, hydrazine, and hydrogen peroxide research. Adv. Aerosp. Eng. 2014, 2014, 1-9.
https://doi.org/10.1155/2014/729313

[6]. Wang, Y.-H.; Jiang, S.-C.; Chen, Y.; Guo, T.; Xia, R.-J.; Tang, X.; He, M.; Xue, W. Correction to: Synthesis and antibacterial activity of novel chalcone derivatives bearing a coumarin moiety. Chem. Pap. 2020, 74, 4141-4142.
https://doi.org/10.1007/s11696-020-01279-y

[7]. Hasan, D.; Grinstein, D.; Kuznetsov, A.; Natan, B.; Schlagman, Z.; Habibi, A.; Elyashiv, M. Green Comparable Alternatives of Hydrazines-Based Monopropellant and Bipropellant Rocket Systems. In Aerospace Engineering; Dekoulis, G., Ed.; IntechOpen: London, England, 2019.
https://doi.org/10.5772/intechopen.82676

[8]. Cui, L.; Ji, C.; Peng, Z.; Zhong, L.; Zhou, C.; Yan, L.; Qu, S.; Zhang, S.; Huang, C.; Qian, X.; Xu, Y. Unique tri-output optical probe for specific and ultrasensitive detection of hydrazine. Anal. Chem. 2014, 86, 4611-4617.
https://doi.org/10.1021/ac5007552

[9]. Dai, X.; Wang, Z.-Y.; Du, Z.-F.; Miao, J.-Y.; Zhao, B.-X. A simple but effective near-infrared ratiometric fluorescent probe for hydrazine and its application in bioimaging. Sens. Actuators B Chem. 2016, 232, 369-374.
https://doi.org/10.1016/j.snb.2016.03.159

[10]. Manna, S. K.; Gangopadhyay, A.; Maiti, K.; Mondal, S.; Mahapatra, A. K. Recent developments in fluorometric and colorimetric chemodosimeters targeted towards hydrazine sensing: Present success and future possibilities. ChemistrySelect 2019, 4, 7219-7245.
https://doi.org/10.1002/slct.201803685

[11]. Xing, M.; Wang, K.; Wu, X.; Ma, S.; Cao, D.; Guan, R.; Liu, Z. A coumarin chalcone ratiometric fluorescent probe for hydrazine based on deprotection, addition and subsequent cyclization mechanism. Chem. Commun. (Camb.) 2019, 55, 14980-14983.
https://doi.org/10.1039/C9CC08174G

[12]. Roy, B.; Bandyopadhyay, S. The design strategies and mechanisms of fluorogenic and chromogenic probes for the detection of hydrazine. Anal. Methods 2018, 10, 1117-1139.
https://doi.org/10.1039/C7AY02866K

[13]. Diyali, N.; Chettri, M.; De, A.; Biswas, B. Synthesis, crystal structure, and antidiabetic property of hydrazine functionalized Schiff base: 1,2-Di(benzylidene)hydrazine. Eur. J. Chem. 2022, 13, 234-240.
https://doi.org/10.5155/eurjchem.13.2.234-240.2265

[14]. Li, M.; He, J.; Wang, Z.; Jiang, Q.; Yang, H.; Song, J.; Yang, Y.; Xu, X.; Wang, S. Novel nopinone-based turn-on fluorescent probe for hydrazine in living cells with high selectivity. Ind. Eng. Chem. Res. 2019, 58, 22754-22762.
https://doi.org/10.1021/acs.iecr.9b04413

[15]. Makarovsky, I.; Markel, G.; Dushnitsky, T.; Eisenkraft, A. Hydrazine - The Space Era Agent. Isr. Med. Assoc. J. 2008, 10, 302-306.

[16]. Desai, K.; Dharaskar, S.; Khalid, M.; Gedam, V. Effectiveness of ionic liquids in extractive-oxidative desulfurization of liquid fuels: a review. Chem. Pap. 2022, 76, 1989-2028.
https://doi.org/10.1007/s11696-021-02038-3

[17]. Li, J.; Cui, Y.; Bi, C.; Feng, S.; Yu, F.; Yuan, E.; Xu, S.; Hu, Z.; Sun, Q.; Wei, D.; Yoon, J. Oligo(ethylene glycol)-functionalized ratiometric fluorescent probe for the detection of hydrazine in vitro and in vivo. Anal. Chem. 2019, 91, 7360-7365.
https://doi.org/10.1021/acs.analchem.9b01223

[18]. Ban, Y.; Wang, R.; Li, Y.; An, Z.; Yu, M.; Fang, C.; Wei, L.; Li, Z. Mitochondria-targeted ratiometric fluorescent detection of hydrazine with a fast response time. New J Chem 2018, 42, 2030-2035.
https://doi.org/10.1039/C7NJ04212D

[19]. Shi, X.; Yin, C.; Zhang, Y.; Wen, Y.; Huo, F. A novel ratiometric and colorimetric fluorescent probe for hydrazine based on ring-opening reaction and its applications. Sens. Actuators B Chem. 2019, 285, 368-374.
https://doi.org/10.1016/j.snb.2019.01.075

[20]. Yu, L.; Liu, H.; Liu, X.; Wang, J.; Xu, J.; Wang, H.; Hou, W.; Zhang, H. Multiple detection for hydrazine based on reduction of the 1,6,7,12-tetrachloroperylene diimide derivative. Chem. Pap. 2018, 72, 1927-1933.
https://doi.org/10.1007/s11696-018-0405-y

[21]. Yu, S.; Wang, S.; Yu, H.; Feng, Y.; Zhang, S.; Zhu, M.; Yin, H.; Meng, X. A ratiometric two-photon fluorescent probe for hydrazine and its applications. Sens. Actuators B Chem. 2015, 220, 1338-1345.
https://doi.org/10.1016/j.snb.2015.07.051

[22]. Rao, N.; Le, Y.; Li, D.; Zhang, Y.; Wang, Q.; Liu, L.; Yan, L. A new phenothiazine-based fluorescent probe for detection of hydrazine with naked-eye color change properties. Chem. Pap. 2022, 76, 267-275.
https://doi.org/10.1007/s11696-021-01859-6

[23]. John Xavier, S. S.; Siva, G.; Ranjani, M.; Divya Rani, S.; Priyanga, N.; Srinivasan, R.; Pannipara, M.; Al-Sehemi, A. G.; Gnana kumar, G. Turn-on fluorescence sensing of hydrazine using MnO2 nanotube-decorated g-C3N4 nanosheets. New J Chem 2019, 43, 13196-13204.
https://doi.org/10.1039/C9NJ01370A

[24]. Yang, X.; Liu, Y.; Wu, Y.; Ren, X.; Zhang, D.; Ye, Y. A NIR ratiometric probe for hydrazine "naked eye" detection and its imaging in living cell. Sens. Actuators B Chem. 2017, 253, 488-494.
https://doi.org/10.1016/j.snb.2017.06.165

[25]. Zhao, J.; Xu, Y.; Li, H.; Lu, A.; Sun, S. A facile intracellular fluorescent probe for detection of hydrazine and its application. New J Chem 2013, 37, 3849-3852.
https://doi.org/10.1039/c3nj00822c

[26]. Muhammad, S.; Bibi, A.; Shafiq-urRehman; Bibi, S.; Al-Sehemi, A. G.; Algarni, H.; Sarwar, F. Exploring the quinoidal oligothiophenes to their robust limit for efficient linear and nonlinear optical response properties. Chem. Pap. 2022, 76, 4273-4288.
https://doi.org/10.1007/s11696-022-02167-3

[27]. Tandel, S.; Patel, N. C.; Kanvah, S.; Patel, P. N. An efficient protocol for the synthesis of novel hetero-aryl chalcone: A versatile synthon for several heterocyclic scaffolds and sensors. J. Mol. Struct. 2022, 1269, 133808.
https://doi.org/10.1016/j.molstruc.2022.133808

[28]. Saha, S.; Das, S.; Sarkar, O.; Chattopadhyay, A.; Rissanen, K.; Sahoo, P. Introduction of a luminescent sensor for tracking trace levels of hydrazine in insect pollinated cropland flowers. New J Chem 2021, 45, 17095-17100.
https://doi.org/10.1039/D1NJ02661E

[29]. Liu, L.; Xing, M.; Han, Y.; Zhang, X.; Li, P.; Cao, D.; Zhao, S.; Ma, L.; Liu, Z. Sensing for hydrazine of a pyrene chalcone derivative with acryloyl terminal group. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2022, 264, 120272.
https://doi.org/10.1016/j.saa.2021.120272

[30]. Goswami, S.; Paul, S.; Manna, A. Fast and ratiometric "naked eye" detection of hydrazine for both solid and vapour phase sensing. New J Chem 2015, 39, 2300-2305.
https://doi.org/10.1039/C4NJ02220C

[31]. Tandel, S. N.; Mistry, P.; Patel, P. N. Novel chalcone scaffolds of benzothiophene as an efficient real time hydrazine sensor: Synthesis and single crystal XRD studies. J. Mol. Struct. 2023, 1274, 134495.
https://doi.org/10.1016/j.molstruc.2022.134495

[32]. Cao, Y. W.; Li, X. L.; He, Y. W. A high selective fluorescent sensor for Ni(II) ion in acetonitrile. Eur. J. Chem. 2017, 8, 314-316.
https://doi.org/10.5155/eurjchem.8.3.314-316.1579

[33]. Rai, S.; Patel, P. N.; Chadha, A. Preparation, characterisation, and crystal structure analysis of (2E,2′E)-3,3′-(1,4-phenylene)bis(1-(2-aminophenyl)prop-2-en-1-one. Crystallogr. Rep. 2016, 61, 1086-1089.
https://doi.org/10.1134/S1063774516070099

[34]. Patel, P. N.; Chadha, A. A simple metal free highly diastereoselective synthesis of heteroaryl substituted (±) cyclohexanols by a branched domino reaction. Tetrahedron 2018, 74, 204-216.
https://doi.org/10.1016/j.tet.2017.11.070

[35]. Patel, P. N.; Chadha, A. Synthesis, single crystal structure and spectroscopic aspects of Benzo[b]thiophene-3-carbaldehyde based chalcones. J. Chem. Crystallogr. 2016, 46, 245-251.
https://doi.org/10.1007/s10870-016-0653-z

[36]. Zhu, Y.; Gong, X.; Li, Z.; Zhao, X.; Liu, Z.; Cao, D.; Guan, R. A simple turn-on ESIPT and PET-based fluorescent probe for detection of Al3+ in real-water sample. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2019, 219, 202-205.
https://doi.org/10.1016/j.saa.2019.04.058

[37]. Qu, J.; Zhang, Z.-H.; Zhang, H.; Weng, Z.-T.; Wang, J.-Y. Diethyl malonate-based turn-on chemical probe for detecting hydrazine and its bio-imaging and environmental applications with large Stokes shift. Front. Chem. 2020, 8, 602125.
https://doi.org/10.3389/fchem.2020.602125

[38]. Hassaneen, H. M.; Shawali, A. S. Regioselective synthesis of some functionalized 3,4'-bis-(pyrazolyl)ketones and chemoselectivity in their reaction with hydrazine hydrate. Eur. J. Chem. 2013, 4, 102-109.
https://doi.org/10.5155/eurjchem.4.2.102-109.723

Supporting Agencies

The work was financially supported by the DST-SERB, Government of India (Project No. DST-SERB/TAR/2019/000089).

Most read articles by the same author(s)

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

License Terms

License Terms

by-nc

Copyright © 2025 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).

Article Sidebar

Main Article Content

Abstract

Article Details

Most read articles by the same author(s)

Downloads

Metrics