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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

The Difference in Sensing Properties Towards Anions between Two Pyridinium Amide-Based Receptors with a Subtle Change of H-Bond Position

Author(s): Wei-tao Gong*, Wei-dong Qu and Guiling Ning

Volume 17, Issue 6, 2020

Page: [472 - 478] Pages: 7

DOI: 10.2174/1570180816666190801100603

Price: $65

Abstract

Two pyridinium amide-based receptors L1 and L2 with a small difference of H-bond position of the amide have been synthesized and characterized. Interestingly, they exhibited a huge difference in sensing towards AcO- and H2PO4 -, respectively. Receptor L1 was found to be ‘naked-eye’ selective for AcO- anions, while receptor L2 showed clear fluorescence enhancement selective to H2PO4 - anion. The recognition ability has been established by fluorescence emission, UV-vis spectra, and 1HNMR titration.

Keywords: Pyridinium amide-based receptors, naked-eye selective, acetate ion, pyridinium, naked-eye, hydrogen bonding.

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[1]
Evans, N.H.; Beer, P.D. Angew. Chem. Int. Ed. , 2014, 53, 11716.
[http://dx.doi.org/10.1002/anie.201309937]
[2]
Zhou, Y.; Zhang, J.F.; Yoon, J. Chem. Rev., 2014, 114(10), 5511-5571.
[http://dx.doi.org/10.1021/cr400352m] [PMID: 24661114]
[3]
Zhang, D.; Jiang, X.; Yang, H.; Su, Z.; Gao, E.; Martinez, A.; Gao, G. Chem. Commun. (Camb.), 2013, 49(55), 6149-6151.
[http://dx.doi.org/10.1039/c3cc43184c] [PMID: 23728525]
[4]
Zhang, R.X.; Li, P.F.; Zhang, W.J.; Li, N.; Zhao, N. J. Mater. Chem. C Mater. Opt. Electron. Devices, 2016, 4, 10479.
[http://dx.doi.org/10.1039/C6TC03696A]
[5]
Cai, J.; Sessler, J.L. Chem. Soc. Rev., 2014, 43(17), 6198-6213.
[http://dx.doi.org/10.1039/C4CS00115J] [PMID: 24871377]
[6]
Gale, P.A.; Howe, E.N.W.; Wu, X. Chem, 2016, 1, 35.
[http://dx.doi.org/10.1016/j.chempr.2016.08.004]
[7]
Wenzel, M.; Hiscock, J.R.; Gale, P.A. Chem. Soc. Rev., 2012, 41(1), 480-520.
[http://dx.doi.org/10.1039/C1CS15257B] [PMID: 22080279]
[8]
Mehdi, H.; Pang, H.; Gong, W.; Dhinakaran, M.K.; Wajahat, A.; Kuang, X.; Ning, G. Org. Biomol. Chem., 2016, 14(25), 5956-5964.
[http://dx.doi.org/0.1039/C6OB00600K] [PMID: 27193611]
[9]
Zhu, L.; Wen, Y.; Liu, H.; Zeng, Z.; Zhao, J.; Jiang, J.; Miao, S. ChemistrySelect, 2018, 3, 2336.
[http://dx.doi.org/10.1002/slct.201702864]
[10]
Mandal, T.N.; Karmakar, A.; Sharma, S.; Ghosh, S.K. Chem. Rec., 2018, 18(2), 154-164.
[http://dx.doi.org/10.1002/tcr.201700033] [PMID: 28880497]
[11]
Bhat, H.R.; Jha, P.C. Chem. Phys., 2017, 19, 14811.
[12]
Xu, Z.; Kim, S.K.; Yoon, J. Chem. Soc. Rev, 2010, 39(5), 1457-1466.
[http://dx.doi.org/10.1039/b918937h] [PMID: 20419201]
[13]
Sancenón, F.; Martínez-Máñez, R.; Miranda, M.A.; Seguí, M-J.; Soto, J. Angew. Chem. Int. Ed. , 2003, 42, 647.
[http://dx.doi.org/10.1002/anie.200390178]
[14]
Houk, R.J.T. Top. Curr. Chem., 2005, 255, 199.
[http://dx.doi.org/10.1007/b101167]
[15]
Fitzmaurice, R.J.; Kyne, G.M.; Douheret, D.; Kilburn, J.D. J. Chem. Soc., Perkin Trans. 1, 2002, 841
[http://dx.doi.org/10.1039/b009041g]
[16]
Hartley, J.H.; James, T.D.; Ward, C.J. J. Chem. Soc., 2000, 0, 3155.
[17]
Gong, W.T.; Na, D.; Fang, L.; Mehdi, H.; Ning, G.L. Org. Biomol. Chem., 2015, 13(7), 1979-1982.
[http://dx.doi.org/10.1039/C4OB02498B] [PMID: 25563510]
[18]
Gong, W.; Hiratani, K. Tetrahedron Lett., 2008, 49, 5655.
[http://dx.doi.org/10.1016/j.tetlet.2008.07.078]
[19]
Gong, W.; Gao, B.; Bao, S.; Ye, J.; Ning, G. J. Incl. Phenom. Macrocycl. Chem., 2011, 72, 481.
[http://dx.doi.org/10.1007/s10847-011-9995-5]
[20]
Gong, W.; Zhang, Q.; Wang, F.; Gao, B.; Lin, Y.; Ning, G. Org. Biomol. Chem., 2012, 10(37), 7578-7583.
[http://dx.doi.org/10.1039/c2ob26135a] [PMID: 22895842]
[21]
Ghosh, K.; Sarkar, A.R.; Sarkar, T.; Panja, S.; Kar, D.; Adv, RSC RSC Advances, 2014, 14, 20114.
[22]
Ghosh, K.; Sarkar, A.R.; Chattopadhyay, A.P. Eur. J. Org. Chem., 2012, 7, 1311.
[http://dx.doi.org/10.1002/ejoc.201101240]
[23]
Ghosh, K.; Kar, D.; Panja, A.; Petsalakis, I.D.; Theodorakopoulos, G. Supramol. Chem., 2014, 26, 856.
[http://dx.doi.org/10.1080/10610278.2014.884716]
[24]
Ghosh, K.; Kar, D. Beilstein J. Org. Chem., 2011, 7, 254-264.
[http://dx.doi.org/10.3762/bjoc.7.34] [PMID: 21448261]
[25]
Ghosh, K.; Saha, I. Org. Biomol. Chem., 2012, 10(47), 9383-9392.
[http://dx.doi.org/10.1039/c2ob26995c] [PMID: 23108334]
[26]
Bao, S.; Gong, W.; Chen, W.; Ye, J.; Lin, Y.; Ning, G. J. Incl. Phenom. Macrocycl. Chem., 2010, 70, 115.
[http://dx.doi.org/10.1007/s10847-010-9869-2]
[27]
Vilar, R. Angew. Chem. Int. Ed. Engl., 2003, 42(13), 1460-1477.
[http://dx.doi.org/10.1002/anie.200200551] [PMID: 12698477]
[28]
Kumar, S.; Singh, P.; Kumar, S. Tetrahedron Lett., 2012, 53, 2248.
[http://dx.doi.org/10.1016/j.tetlet.2012.02.084]
[29]
Upadhyay, K.K.; Kumar, A.; Zhao, J.; Mishra, R.K. Talanta, 2010, 81(1-2), 714-721.
[http://dx.doi.org/10.1016/j.talanta.2010.01.005] [PMID: 20188987]
[30]
Lin, W.; Yuan, L.; Cao, Z.; Feng, Y.; Long, L. Chemistry, 2009, 15(20), 5096-5103.
[http://dx.doi.org/10.1002/chem.200802751] [PMID: 19343759]
[31]
Caballero, A.; Martínez, R.; Lloveras, V.; Ratera, I. J. Am. Chem. Soc., 2005, 127, 15666.
[http://dx.doi.org/10.1021/ja0545766] [PMID: 16277484]
[32]
Shortreed, M.; Kopelman, R. Anal. Chem., 1996, 68, 1414.
[http://dx.doi.org/10.1021/ac950944k] [PMID: 8651501]
[33]
Nakahara, Y.; Kida, T.; Nakatsuji, Y.; Akashi, M. Org. Biomol. Chem., 2005, 3, 1781.
[http://dx.doi.org/10.1039/b501233c] [PMID: 15858664]
[34]
Conners, K.A. New York; , 1987, p. 147.
[35]
Job, P. Ann. Chim. Appl., 1928, 9, 113.

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