Copyright (c) 2024 Chandana Pramanik
This work is licensed under a Creative Commons Attribution 4.0 International License.
A Novel Phenolate-Thiadiazolyl Based Carbonate Sensor: Design, Synthesis and Characterization
Corresponding Author(s) : Chandana Pramanik
Asian Journal of Chemistry,
Vol. 37 No. 1 (2025): Vol 37 Issue 1, 2025
Abstract
A highly selective and sensitive phenolate-thiadiazolyl based colorimetric as well as fluorometric chemosensor (E)-2-(((5-(2-chlorophenyl)-1,3,4-thiadiazol-2-yl)imino)methyl)-6-ethoxy phenol (HL) has been designed and synthesized by Schiff base reaction. This probe has been characterized by spectroscopic techniques such as NMR (1H), ESI-MS and IR spectroscopy. This probe, HL can detect selectively carbonate anion in tris-HCl buffer solution (10 mM, pH 7.2, 1:1 v/v) medium by colorimetric and fluorometric method. The limit of detection of the probe towards carbonate is 0.435 µM. The 1:1 stoichiometry of binding of HL and carbonate was supported by ESI-MS spectra, TGA and Job’s plot analysis.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- V.R. Martínez-Máñez and F. Sancenón, Chem. Rev., 103, 4419 (2003); https://doi.org/10.1021/cr010421e
- K. Berend, L.H. van Hulsteijn and R.O.B. Gans, Eur. J. Internal Med., 23, 203 (2012); https://doi.org/10.1016/j.ejim.2011.11.013
- M. Wenzel, J.R. Hiscock and P.A. Gale, Chem. Soc. Rev., 41, 480 (2012); https://doi.org/10.1039/C1CS15257B
- S.-H. Chung and S. Kuyucak, Biochim. Biophys. Acta Biomembranes, 1565, 267 (2002); https://doi.org/10.1016/S0005-2736(02)00574-6
- J. Pérez and L. Riera, Chem. Soc. Rev., 37, 2658 (2008); https://doi.org/10.1039/b707074h
- J.W. Steed, Chem. Soc. Rev., 38, 506 (2009); https://doi.org/10.1039/B810364J
- J.D. Toner and D.C. Catling, Proc. Natl. Acad. Sci. USA, 117, 883 (2020); https://doi.org/10.1073/pnas.1916109117
- Z. Liu, J.-C. Rossi and R. Pascal, Life, 9, 26 (2019); https://doi.org/10.3390/life9010026
- T.J. Jentsch, V. Stein, F. Weinreich and A.A. Zdebik, Physiol. Rev., 82, 503 (2002); https://doi.org/10.1152/physrev.00029.2001
- Solihin, IOP Conf. Ser.: Earth Environ. Sci., 118, 012065 (2018); https://doi.org/10.1088/1755-1315/118/1/012065
- F.W. Tegethoff, Calcium Carbonate: From the Cretaceous Period into the 21st Century, Springer (2001).
- L.D. Chen, D. Mandal, G. Pozzi, J.A. Gladysz and P. Bühlmann, J. Am. Chem. Soc., 133, 20869 (2011); https://doi.org/10.1021/ja207680e
- A.H. England, A.M. Duffin, C.P. Schwartz, J.S. Uejio, D. Prendergast and R.J. Saykally, Chem. Phys. Lett., 514, 187 (2011); https://doi.org/10.1016/j.cplett.2011.08.063
- A.C. Tas, Int. J. Appl. Ceram. Technol., 6, 53 (2009); https://doi.org/10.1111/j.1744-7402.2008.02252.x
- R. Demichelis, P. Raiteri, J.D. Gale, D. Quigley and D. Gebauer, Nat. Commun., 2, 590 (2011); https://doi.org/10.1038/ncomms1604
- H. Zhao, S.-J. Park, F. Shi, Y. Fu, V. Battaglia, P.N. Ross Jr. and G. Liu, J. Electrochem. Soc., 161, A194 (2014); https://doi.org/10.1149/2.095401jes
- D. Aurbach, J.S. Gnanaraj, W. Geissler and M. Schmidt, J. Electrochem. Soc., 151, A23 (2004); https://doi.org/10.1149/1.1631820
- N.-N. Sun and B. Yan, Dyes Pigments, 142, 1 (2017); https://doi.org/10.1016/j.dyepig.2017.03.014
- C. Han, Z. Cui, Z. Zou, Sabahaiti, D. Tian and H. Li, Photochem. Photobiol. Sci., 9, 1269 (2010); https://doi.org/10.1039/c0pp00119h
- Y.-N. Lu, J.-L. Peng, X. Zhou, J.-Z. Wu, Y.-C. Ou and Y.-P. Cai, CrystEngComm, 20, 7574 (2018); https://doi.org/10.1039/C8CE01414K
- A. Ghorai, J. Mondal, R. Chandra and G.K. Patra, RSC Adv., 6, 72185 (2016); https://doi.org/10.1039/C5RA24549D
- Y.S. Choi, L. Lvova, J.H. Shin, S.H. Oh, C.S. Lee, B.H. Kim, G.S. Cha and H. Nam, Anal. Chem., 74, 2435 (2002); https://doi.org/10.1021/ac0108459
- M. Zougagh, Talanta, 65, 29 (2004); https://doi.org/10.1016/j.talanta.2004.05.010
- X. Wang, Q. Yang, Y. Cao, J. Zhou, H. Hao, Y. Liang, Asian J. Pharm., 11, 722 (2016); https://doi.org/10.1002/asia.201501198
- R. Motais, B. Fievet, F. Garcia-Romeu, S., Am. J. Phys. Anthropol., 256, C728 (1989); https://doi.org/10.1152/ajpcell.1989.256.4
- F. Gazeau, J.P. Gattuso, M. Greaves, H. Elderfield, J. Peene, C.H. Heip and J.J. Middelburg, PLoS One, 6, e23010 (2011); https://doi.org/10.1371/journal.pone.0023010
- L. Beck, I. Caffy, E. Delqué-Koliè, C. Moreau, J.-P. Dumoulin, M. Perron, H. Guichard and V. Jeammet, Commun. Chem., 1, e34 (2018); https://doi.org/10.1038/s42004-018-0034-y
- S. Contini and C. Scarpignato, World J. Gastroenterol., 19, 3918 (2013); https://doi.org/10.3748/wjg.v19.i25.3918
- E.E. Burt and A.H. Rau, Drug Dev. Ind. Pharm., 20, 2955 (1994); https://doi.org/10.3109/03639049409041960
- R.G. Amundson, J. Trask and E. Pendall, Soil Sci. Soc. Am. J., 52, 880 (1988); https://doi.org/10.2136/sssaj1988.03615995005200030050x
- J. Bobacka, M. Maj-Zurawska and A. Lewenstam, Biosens. Bioelectron., 53, 245 (2003); https://doi.org/10.1016/s0956-5663(02)00179-3
- O. Doka, D. Bicanic, M. Szücs and M. Lubbers, Appl. Spectrosc., 52, 1526 (1998); https://doi.org/10.1366/0003702981943239
- L. He, C. Liu and J.H. Xin, Sens. Actuators B Chem., 213, 181 (2015); https://doi.org/10.1016/j.snb.2015.02.060
- G. Cui, J. S. Lee, S. J. Kim, H. Nam, G. Sig Cha and H. D. Kim, Analyst, 123, 1855 (1998); https://doi.org/10.1039/A802872I
- K. Tsukada, Y. Miyahara, Y. Shibata and H. Miyagi, Sens. Actuators B Chem., 2, 291 (1990); https://doi.org/10.1016/0925-4005(90)80156-T
- R.K. Meruva and M.E. Meyerhoff, Biosens. Bioelectron., 13, 201 (1998); https://doi.org/10.1016/S0956-5663(97)00097-3
- H. Kaur, A. Riya, A. Singh, H. Singh, U. Ranjan Lal, A. Kumar and M.V.N.L. Chaitanya, Spectrochim. Acta A Mol. Biomol. Spectrosc., 303, 123270 (2023); https://doi.org/10.1016/j.saa.2023.123270
- K. Krämer, R. Kang, L.M. Grimm, L. De Cola, P. Picchetti and F. Biedermann, Chem. Rev., 122, 3459 (2022); https://doi.org/10.1021/acs.chemrev.1c00746
- D. Wu, A.C. Sedgwick, T. Gunnlaugsson, E.U. Akkaya, J. Yoon and T.D. James, Chem. Soc. Rev., 46, 7105 (2017); https://doi.org/10.1039/C7CS00240H
- J. Shao, H. Lin and H.K. Lin, Talanta, 75, 1015 (2008); https://doi.org/10.1016/j.talanta.2007.12.041
- B. Kuswandi, N. N/a, W. Verboom and D.N. Reinhoudt, Sensors, 6, 978 (2006); https://doi.org/10.3390/s6080978
- K. Ghosh and S. Adhikari, Tetrahedron Lett., 47, 8165 (2006); https://doi.org/10.1016/j.tetlet.2006.09.035
- A.K. Jain, J. Raisoni, R. Kumar and S. Jain, Int. J. Environ. Anal. Chem., 87, 553 (2007); https://doi.org/10.1080/03067310701272905
- G.A.E. Mostafa, Int. J. Environ. Anal. Chem., 88, 435 (2008); https://doi.org/10.1080/03067310701717735
- M.T. Oms, P.A.C. Jongejan, A.C. Veltkamp, G.P. Wyers and J. Slanina, Int. J. Environ. Anal. Chem., 62, 207 (1996); https://doi.org/10.1080/03067319608028134
- G. Prabakaran, G. Narmatha, K. Velmurugan, A. Basith, R. Karthick, G. Velraj, R.S. Kumar and R. Nandhakumar, J. Mol. Struct., 1295, 136684 (2024); https://doi.org/10.1016/j.molstruc.2023.136684
- Y. Zheng, C. Tan, G.P.C. Drummen and Q. Wang, Spectrochim. Acta A Mol. Biomol. Spectrosc., 96, 387 (2012); https://doi.org/10.1016/j.saa.2012.05.064
- S. Mizukami, T. Nagano, Y. Urano, A. Odani and K.A. Kikuchi, J. Am. Chem. Soc., 124, 3920 (2002); https://doi.org/10.1021/ja0175643
- R.M. Duke, E.B. Veale, F.M. Pfeffer, P.E. Kruger and T. Gunnlaugsson, Chem. Soc. Rev., 39, 3936 (2010); https://doi.org/10.1039/b910560n
- H.K. Lee, H. Oh, K.C. Nam and S. Jeon, Sens. Actuators B Chem., 106, 207 (2005); https://doi.org/10.1016/j.snb.2004.07.032
- J. Wu, C. Li, Q. Chen and J. Zhao, Dyes Pigments, 195, 109709 (2021); https://doi.org/10.1016/j.dyepig.2021.109709
- Q. Li, Y. Guo, J. Xu and S. Shao, Sens. Actuators B Chem., 158, 427 (2011); https://doi.org/10.1016/j.snb.2011.06.007
- R. Dwivedi, P. Sharma, A. Sisodiya, M.S. Batra and R. Prasad, J. Catal., 345, 245 (2017); https://doi.org/10.1016/j.jcat.2016.10.033
- C. Pramanik, A. Jana, P. Brandao, P. Bera, S. Khatua, S. Majumdar, B. Mandal, A. Aher, S. Kumar Manna and P. Bera, Spectrochim. Acta A Mol. Biomol. Spectrosc., 315, 124233 (2024); https://doi.org/10.1016/j.saa.2024.124233
- W.S. El-Serwy, W.S. El-Serwy, H.S. Mohamed, Russ. J. Bioorganic Chem., 47, 158 (2021); https://doi.org/10.1134/S1068162021010155
- A.D. Becke, J. Chem. Phys., 98, 5648 (1993); https://doi.org/10.1063/1.464913
- D. Zhang, X. Jiang, H. Yang, Z. Su, E. Gao, A. Martinez and G. Gao, Chem. Commun., 49, 6149 (2013); https://doi.org/10.1039/c3cc43184c
- S. Verma, V. Ravichandiran and N. Ranjan, Spectrochim. Acta A Mol. Biomol. Spectrosc., 255, 119624 (2021); https://doi.org/10.1016/j.saa.2021.119624
- S.N.K. Elmas, F. Ozen, K. Koran, A.O. Gorgulu, G. Sadi, I. Yilmaz and S. Erdemir, Talanta, 188, 614 (2018); https://doi.org/10.1016/j.talanta.2018.06.036
- S.N.K. Elmas, A. Karagoz, D. Aydin, F.N. Arslan, G. Sadi and I. Yilmaz, Talanta, 226, 122166 (2021); https://doi.org/10.1016/j.talanta.2021.122166
- C. Sun, J. Sun, P. Che, Z. Chang, W. Li and F. Qiu, J. Lumin., 188, 246 (2017); https://doi.org/10.1016/j.jlumin.2017.04.005
- C.N. Carroll, J.J. Naleway, M.M. Haley and D.W. Johnson, Chem. Soc. Rev., 39, 3875 (2010); https://doi.org/10.1039/b926231h
- H. Xu, H. Ding, C. Fan, G. Liu and S. Pu, Tetrahedron, 74, 3489 (2018); https://doi.org/10.1016/j.tet.2018.02.032
- H. Tavallali, G. Deilamy-Rad, A. Parhami and S. Lohrasbi, Talanta, 149, 168 (2016); https://doi.org/10.1016/j.talanta.2015.11.057
References
V.R. Martínez-Máñez and F. Sancenón, Chem. Rev., 103, 4419 (2003); https://doi.org/10.1021/cr010421e
K. Berend, L.H. van Hulsteijn and R.O.B. Gans, Eur. J. Internal Med., 23, 203 (2012); https://doi.org/10.1016/j.ejim.2011.11.013
M. Wenzel, J.R. Hiscock and P.A. Gale, Chem. Soc. Rev., 41, 480 (2012); https://doi.org/10.1039/C1CS15257B
S.-H. Chung and S. Kuyucak, Biochim. Biophys. Acta Biomembranes, 1565, 267 (2002); https://doi.org/10.1016/S0005-2736(02)00574-6
J. Pérez and L. Riera, Chem. Soc. Rev., 37, 2658 (2008); https://doi.org/10.1039/b707074h
J.W. Steed, Chem. Soc. Rev., 38, 506 (2009); https://doi.org/10.1039/B810364J
J.D. Toner and D.C. Catling, Proc. Natl. Acad. Sci. USA, 117, 883 (2020); https://doi.org/10.1073/pnas.1916109117
Z. Liu, J.-C. Rossi and R. Pascal, Life, 9, 26 (2019); https://doi.org/10.3390/life9010026
T.J. Jentsch, V. Stein, F. Weinreich and A.A. Zdebik, Physiol. Rev., 82, 503 (2002); https://doi.org/10.1152/physrev.00029.2001
Solihin, IOP Conf. Ser.: Earth Environ. Sci., 118, 012065 (2018); https://doi.org/10.1088/1755-1315/118/1/012065
F.W. Tegethoff, Calcium Carbonate: From the Cretaceous Period into the 21st Century, Springer (2001).
L.D. Chen, D. Mandal, G. Pozzi, J.A. Gladysz and P. Bühlmann, J. Am. Chem. Soc., 133, 20869 (2011); https://doi.org/10.1021/ja207680e
A.H. England, A.M. Duffin, C.P. Schwartz, J.S. Uejio, D. Prendergast and R.J. Saykally, Chem. Phys. Lett., 514, 187 (2011); https://doi.org/10.1016/j.cplett.2011.08.063
A.C. Tas, Int. J. Appl. Ceram. Technol., 6, 53 (2009); https://doi.org/10.1111/j.1744-7402.2008.02252.x
R. Demichelis, P. Raiteri, J.D. Gale, D. Quigley and D. Gebauer, Nat. Commun., 2, 590 (2011); https://doi.org/10.1038/ncomms1604
H. Zhao, S.-J. Park, F. Shi, Y. Fu, V. Battaglia, P.N. Ross Jr. and G. Liu, J. Electrochem. Soc., 161, A194 (2014); https://doi.org/10.1149/2.095401jes
D. Aurbach, J.S. Gnanaraj, W. Geissler and M. Schmidt, J. Electrochem. Soc., 151, A23 (2004); https://doi.org/10.1149/1.1631820
N.-N. Sun and B. Yan, Dyes Pigments, 142, 1 (2017); https://doi.org/10.1016/j.dyepig.2017.03.014
C. Han, Z. Cui, Z. Zou, Sabahaiti, D. Tian and H. Li, Photochem. Photobiol. Sci., 9, 1269 (2010); https://doi.org/10.1039/c0pp00119h
Y.-N. Lu, J.-L. Peng, X. Zhou, J.-Z. Wu, Y.-C. Ou and Y.-P. Cai, CrystEngComm, 20, 7574 (2018); https://doi.org/10.1039/C8CE01414K
A. Ghorai, J. Mondal, R. Chandra and G.K. Patra, RSC Adv., 6, 72185 (2016); https://doi.org/10.1039/C5RA24549D
Y.S. Choi, L. Lvova, J.H. Shin, S.H. Oh, C.S. Lee, B.H. Kim, G.S. Cha and H. Nam, Anal. Chem., 74, 2435 (2002); https://doi.org/10.1021/ac0108459
M. Zougagh, Talanta, 65, 29 (2004); https://doi.org/10.1016/j.talanta.2004.05.010
X. Wang, Q. Yang, Y. Cao, J. Zhou, H. Hao, Y. Liang, Asian J. Pharm., 11, 722 (2016); https://doi.org/10.1002/asia.201501198
R. Motais, B. Fievet, F. Garcia-Romeu, S., Am. J. Phys. Anthropol., 256, C728 (1989); https://doi.org/10.1152/ajpcell.1989.256.4
F. Gazeau, J.P. Gattuso, M. Greaves, H. Elderfield, J. Peene, C.H. Heip and J.J. Middelburg, PLoS One, 6, e23010 (2011); https://doi.org/10.1371/journal.pone.0023010
L. Beck, I. Caffy, E. Delqué-Koliè, C. Moreau, J.-P. Dumoulin, M. Perron, H. Guichard and V. Jeammet, Commun. Chem., 1, e34 (2018); https://doi.org/10.1038/s42004-018-0034-y
S. Contini and C. Scarpignato, World J. Gastroenterol., 19, 3918 (2013); https://doi.org/10.3748/wjg.v19.i25.3918
E.E. Burt and A.H. Rau, Drug Dev. Ind. Pharm., 20, 2955 (1994); https://doi.org/10.3109/03639049409041960
R.G. Amundson, J. Trask and E. Pendall, Soil Sci. Soc. Am. J., 52, 880 (1988); https://doi.org/10.2136/sssaj1988.03615995005200030050x
J. Bobacka, M. Maj-Zurawska and A. Lewenstam, Biosens. Bioelectron., 53, 245 (2003); https://doi.org/10.1016/s0956-5663(02)00179-3
O. Doka, D. Bicanic, M. Szücs and M. Lubbers, Appl. Spectrosc., 52, 1526 (1998); https://doi.org/10.1366/0003702981943239
L. He, C. Liu and J.H. Xin, Sens. Actuators B Chem., 213, 181 (2015); https://doi.org/10.1016/j.snb.2015.02.060
G. Cui, J. S. Lee, S. J. Kim, H. Nam, G. Sig Cha and H. D. Kim, Analyst, 123, 1855 (1998); https://doi.org/10.1039/A802872I
K. Tsukada, Y. Miyahara, Y. Shibata and H. Miyagi, Sens. Actuators B Chem., 2, 291 (1990); https://doi.org/10.1016/0925-4005(90)80156-T
R.K. Meruva and M.E. Meyerhoff, Biosens. Bioelectron., 13, 201 (1998); https://doi.org/10.1016/S0956-5663(97)00097-3
H. Kaur, A. Riya, A. Singh, H. Singh, U. Ranjan Lal, A. Kumar and M.V.N.L. Chaitanya, Spectrochim. Acta A Mol. Biomol. Spectrosc., 303, 123270 (2023); https://doi.org/10.1016/j.saa.2023.123270
K. Krämer, R. Kang, L.M. Grimm, L. De Cola, P. Picchetti and F. Biedermann, Chem. Rev., 122, 3459 (2022); https://doi.org/10.1021/acs.chemrev.1c00746
D. Wu, A.C. Sedgwick, T. Gunnlaugsson, E.U. Akkaya, J. Yoon and T.D. James, Chem. Soc. Rev., 46, 7105 (2017); https://doi.org/10.1039/C7CS00240H
J. Shao, H. Lin and H.K. Lin, Talanta, 75, 1015 (2008); https://doi.org/10.1016/j.talanta.2007.12.041
B. Kuswandi, N. N/a, W. Verboom and D.N. Reinhoudt, Sensors, 6, 978 (2006); https://doi.org/10.3390/s6080978
K. Ghosh and S. Adhikari, Tetrahedron Lett., 47, 8165 (2006); https://doi.org/10.1016/j.tetlet.2006.09.035
A.K. Jain, J. Raisoni, R. Kumar and S. Jain, Int. J. Environ. Anal. Chem., 87, 553 (2007); https://doi.org/10.1080/03067310701272905
G.A.E. Mostafa, Int. J. Environ. Anal. Chem., 88, 435 (2008); https://doi.org/10.1080/03067310701717735
M.T. Oms, P.A.C. Jongejan, A.C. Veltkamp, G.P. Wyers and J. Slanina, Int. J. Environ. Anal. Chem., 62, 207 (1996); https://doi.org/10.1080/03067319608028134
G. Prabakaran, G. Narmatha, K. Velmurugan, A. Basith, R. Karthick, G. Velraj, R.S. Kumar and R. Nandhakumar, J. Mol. Struct., 1295, 136684 (2024); https://doi.org/10.1016/j.molstruc.2023.136684
Y. Zheng, C. Tan, G.P.C. Drummen and Q. Wang, Spectrochim. Acta A Mol. Biomol. Spectrosc., 96, 387 (2012); https://doi.org/10.1016/j.saa.2012.05.064
S. Mizukami, T. Nagano, Y. Urano, A. Odani and K.A. Kikuchi, J. Am. Chem. Soc., 124, 3920 (2002); https://doi.org/10.1021/ja0175643
R.M. Duke, E.B. Veale, F.M. Pfeffer, P.E. Kruger and T. Gunnlaugsson, Chem. Soc. Rev., 39, 3936 (2010); https://doi.org/10.1039/b910560n
H.K. Lee, H. Oh, K.C. Nam and S. Jeon, Sens. Actuators B Chem., 106, 207 (2005); https://doi.org/10.1016/j.snb.2004.07.032
J. Wu, C. Li, Q. Chen and J. Zhao, Dyes Pigments, 195, 109709 (2021); https://doi.org/10.1016/j.dyepig.2021.109709
Q. Li, Y. Guo, J. Xu and S. Shao, Sens. Actuators B Chem., 158, 427 (2011); https://doi.org/10.1016/j.snb.2011.06.007
R. Dwivedi, P. Sharma, A. Sisodiya, M.S. Batra and R. Prasad, J. Catal., 345, 245 (2017); https://doi.org/10.1016/j.jcat.2016.10.033
C. Pramanik, A. Jana, P. Brandao, P. Bera, S. Khatua, S. Majumdar, B. Mandal, A. Aher, S. Kumar Manna and P. Bera, Spectrochim. Acta A Mol. Biomol. Spectrosc., 315, 124233 (2024); https://doi.org/10.1016/j.saa.2024.124233
W.S. El-Serwy, W.S. El-Serwy, H.S. Mohamed, Russ. J. Bioorganic Chem., 47, 158 (2021); https://doi.org/10.1134/S1068162021010155
A.D. Becke, J. Chem. Phys., 98, 5648 (1993); https://doi.org/10.1063/1.464913
D. Zhang, X. Jiang, H. Yang, Z. Su, E. Gao, A. Martinez and G. Gao, Chem. Commun., 49, 6149 (2013); https://doi.org/10.1039/c3cc43184c
S. Verma, V. Ravichandiran and N. Ranjan, Spectrochim. Acta A Mol. Biomol. Spectrosc., 255, 119624 (2021); https://doi.org/10.1016/j.saa.2021.119624
S.N.K. Elmas, F. Ozen, K. Koran, A.O. Gorgulu, G. Sadi, I. Yilmaz and S. Erdemir, Talanta, 188, 614 (2018); https://doi.org/10.1016/j.talanta.2018.06.036
S.N.K. Elmas, A. Karagoz, D. Aydin, F.N. Arslan, G. Sadi and I. Yilmaz, Talanta, 226, 122166 (2021); https://doi.org/10.1016/j.talanta.2021.122166
C. Sun, J. Sun, P. Che, Z. Chang, W. Li and F. Qiu, J. Lumin., 188, 246 (2017); https://doi.org/10.1016/j.jlumin.2017.04.005
C.N. Carroll, J.J. Naleway, M.M. Haley and D.W. Johnson, Chem. Soc. Rev., 39, 3875 (2010); https://doi.org/10.1039/b926231h
H. Xu, H. Ding, C. Fan, G. Liu and S. Pu, Tetrahedron, 74, 3489 (2018); https://doi.org/10.1016/j.tet.2018.02.032
H. Tavallali, G. Deilamy-Rad, A. Parhami and S. Lohrasbi, Talanta, 149, 168 (2016); https://doi.org/10.1016/j.talanta.2015.11.057