Publication Cover
Journal of Environmental Science and Health, Part B
Pesticides, Food Contaminants, and Agricultural Wastes
Volume 53, 2018 - Issue 10
357
Views
5
CrossRef citations to date
0
Altmetric
Original Articles

Pesticide binding and urea-induced controlled release applications with calixarene naphthalimide molecules by host–guest complexation

, &
Pages 669-676 | Received 04 Jan 2018, Accepted 26 Apr 2018, Published online: 29 May 2018

References

  • Zeng, X.; Ma, J.; Luo, L.; Yang, L.; Cao, X.; Tian, D.; Li, H. Pesticide macroscopic recognition by a naphthol-appended calix[4]arene. Org. Lett. 2015, 17, 2976–2979. DOI: 10.1021/acs.orglett.5b01075.
  • Ni, X. L.; Zeng X.; Redshaw, C.; Yamato, T. Ratiometric fluorescent receptors for both Zn2+ and H2PO4− ions based on a pyrenyl-linked triazole-modified homooxacalix[3]arene: A potential molecular traffic signal with an R-S latch logic circuit. J. Org. Chem. 2011, 76, 5696–5702. DOI: 10.1021/jo2007303.
  • Chawla, H.; Sahu, S.; Shrivastava, R. A novel calix[4]arene-based neutral semicarbazone receptor for anion recognition. Tetrahedron Lett. 2007, 48, 6054–6058. DOI: 10.1016/j.tetlet.2007.06.075.
  • Durmaz, M.; Bozkurt, S.; Naziroglu, H. N.; Yilmaz, M.; Sirit, A. Chiral calix[4]arenes bearing aminonaphthol moieties as membrane carriers for amino acid methyl esters and mandelic acid. Tetrahedron: Asym. 2011, 22, 791–796. DOI: 10.1016/j.tetasy.2011.04.019.
  • Delattre, F.; Cazier, F.; Cazier, F.; Tine, A. Use a fluorescent molecular sensor for the detection of pesticides and herbicides in water. Curr. Anal. Chem. 2009, 5, 48–52. DOI: 10.2174/157341109787047871.
  • Luo, L.; Zhang, X.; Feng, N.; Tian, D.; Deng, H.; Li, H. Cation-induced pesticide binding and release by a functionalized calix[4]arene molecular host. Sci. Rep. 2015, 11, 8982–8989. DOI: 10.1038/srep08982.
  • Wang, X.; Mu, Z.; Shangguan, F.; Liu, R.; Pu, Y.; Yin, L. Rapid and sensitive suspension array for multiplex detection of organophosphorus pesticides and carbamate pesticides based on silica-hydrogel hybrid microbeads. J. Hazard. Mater. 2014, 273, 287–292. DOI: 10.1016/j.jhazmat.2014.03.006.
  • Nishi, K.; Isobe, S.-I.; Zhu, Y.; Kiyama, R. Fluorescence-based bioassays for the detection and evaluation of food materials. Sensors. 2015, 15, 25831–25867. DOI: 10.3390/s151025831.
  • Lin, C. F.; Liu, Y. H.; Peng, S. M.; Chiu, S. H. Precise facial control in threading guests into a molecular cage and the formation of a turtlelike supramolecular complex. Angew. Chem. Int. Ed. 2006, 45, 3176–3181. DOI: 10.1002/anie.200600336.
  • Jeon, Y. M.; Kim, J.; Whang, D.; Kim, K. Molecular container assembly capable of controlling binding and release of its guest molecules: reversible encapsulation of organic molecules in sodium ion complexed cucurbituril. J. Am. Chem. Soc. 1996, 118, 9790–9791. DOI: 10.1021/ja962071x.
  • Teyssandier, J.; De Feyter, S.; Mali, K. S. Host–guest chemistry in two-dimensional supramolecular networks. Chem. Commun. 2016, 52, 11465–11487. DOI: 10.1039/C6CC05256H.
  • Rizzuto, F. J.; Wu, W.-Y.; Ronson, T. K.; Nitschke, J. R. Peripheral templation generates an Mıı 6l4 guest–binding capsule. Angew. Chem. Int. Ed. Engl. 2016, 55, 7958–7962. DOI: 10.1002/anie.201602135.
  • Coly, A.; Aaron, J. J. Cyclodextrin-enhanced fluorescence and photochemically-induced fluorescence determination of five aromatic pesticides in water. Anal. Chim. Acta. 1998, 360, 129–141. DOI: 10.1016/S0003-2670(97)00721-6.
  • Sun, S.; Li, F.; Liu, F.; Wang, J.; Peng, X. Fluorescence detecting of paraquat using host-guest chemistry with cucurbit[8]uril. Sci. Rep. 2014, 4, 3570–3575. DOI: 10.1038/srep03570.
  • Gutsche, C. D.; Nam, K. C. Calixarenes 22. Synthesis, properties, and metal complexation of aminocalixarenes. J. Am. Chem. Soc. 1988, 110, 6153–6162. DOI: 10.1021/ja00226a034.
  • Bayrakci, M.; Ertul, S.; Yilmaz, M. Phase solubility studies of poorly soluble drug molecules by using o-phosphorylated calixarenes as drug-solubilizing agents. J. Chem. Eng. Data. 2012, 57, 233–239. DOI: 10.1021/je200992c.
  • Kim, J. S.; Quang, D. T. Calixarene-derived fluorescent probes. Chem. Rev. 2007, 107, 3780–3799. DOI: 10.1021/cr068046j.
  • Deska, M.; Dondela, B.; Sliwa, W. Selected applications of calixarene derivatives. Arkivoc. 2015, 6, 393–416.
  • Collins, E. M.; McKervey, M. A.; Madigan, E.; Moran, M. B.; Owens, M.; Ferguson, G.; Harris, S. J. Chemical modified calix[4]arene. Regioselective synthesis of 1,3-(distal) derivatives and related compounds. X-ray crystal structure of a diphenol–dinitrile. J. Chem. Soc., Perkin Trans. 1991, 1, 3137–3142. DOI: 10.1039/p19910003137.
  • Ertul, S.; Bayrakci, M.; Yilmaz, M. Removal of chromate and phosphate anion from aqueous solutions using calix[4]aren receptors containing proton switchable units. J. Hazard. Mater. 2010, 181, 1059–1065. DOI: 10.1016/j.jhazmat.2010.05.121.
  • Yu, G.; Jie, K.; Huang, F. Supramolecular amphiphiles based on host-guest molecular recognition motifs. Chem. Rev. 2015, 115, 7240–7303. DOI: 10.1021/cr5005315.
  • Arena, G.; Casnati, A.; Contino, A.; Lombardo, G. G.; Sciotto, D.; Ungaro, R. Water‐soluble calixarene hosts that specifically recognize the trimethylammonium group or the benzene ring of aromatic ammonium cations: A combined 1HNMR, calorimetric, and molecular mechanics investigation. Chem. Eur. J. 1999, 5, 738–744. DOI: 10.1002/(SICI)1521-3765(19990201)5:2%3c738::AID-CHEM738%3e3.0.CO;2-6.
  • Lakowicz, J. R. Principles of Fluorescence Spectroscopy, 2nd ed. Kluwer Academic/Plenum Publishers: New York, 1999; pp. 238–264.
  • Liu, H.; Li, F.-X.; Yan, P.; Wang, D. J.; Hu, Y. J.; Zheng, J. Fluorescence quenching study of 2,6-bis(5-(4-methylphenyl)-1-H-pyrazol-3-yl)pyridine with metal ions. Spectrochim. Acta, Part A. 2005, 145, 588–593. DOI: 10.1016/j.saa.2015.03.049.
  • He, L.; Wang, X.; Liu, B.; Wang, J.; Sun, Y.; Gao, E.; Xu, S. Study on the interaction between promethazine hydrochloride and bovine serum albumin by fluorescence spectroscopy. J. Lumin. 2011, 131, 285–290. DOI: 10.1016/j.jlumin.2010.10.014.
  • Elabd, A. A. A new fluorescent sensor for determination of thorium by thin film of 2-(acetyloxy)-N-(5-nitro-2-thiazolyl)-benzamide embedded in sol–gel matrix. RSC Adv. 2016, 6, 45525–45532. DOI: 10.1039/C6RA04226K.
  • Salgado, E. N.; Radford, R. J.; Tezcan, F. A. Metal-directed protein self-assembly. Acc. Chem. Res. 2010, 43, 661–672. DOI: 10.1021/ar900273t.
  • Jeon, Y. M.; Kim, J.; Whang, D.; Kim, K. Molecular container assembly capable of controlling binding and release of its guest molecules: reversible encapsulation of organic molecules in sodium ıon complexed cucurbituril. J. Am. Chem. Soc. 1996, 118, 9790–9791. DOI: 10.1021/ja962071x.
  • Sindelar, V.; Silvi, S.; Kaifer, A. E. Switching a molecular shuttle on and off: Simple, pH-controlled pseudorotaxanesbased on cucurbit[7]uril. Chem. Commun. 2006, 20, 2185–2187. DOI: 10.1039/b601959e.
  • Wanyika, H.; Gatebe, E.; Kioni, P.; Tang, Z.; Gao, Y. Mesoporous silica nanoparticles carrier for urea: Potential applications in agrochemical delivery systems. J. Nanosci. Nanotechnol. 2012, 12, 2221–2228. DOI: 10.1166/jnn.2012.5801.
  • Celis, R.; Hermosin, M. C.; Carrizosa, M. J.; Cornejo, J. Inorganic and organic clays as carriers for controlled release of the herbicide hexazinone. J. Agric. Food. Chem. 2002, 50, 2324–2330. DOI: 10.1021/jf011360o.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.