The preparation and characterization of photo-responsive sol–gel materials for 2,4-dichlorophenoxyacetic acid by surface imprinting
Source abstract
Abstract
The primary objective of this work is to develop a photo-responsive surface molecularly imprinted polymer (SMIP) for 2,4-dichlorophenoxyacetic acid (2,4-D) to overcome the shortcomings of conventional molecularly imprinted polymers. A photo-responsive functional monomer was firstly prepared by covalent connecting azobenzene and 2,4-D. The photo-responsive SMIP was then prepared on SiO2 nanoparticles via sol–gel process, and 2,4-D was removed via hydrolysis in acid. The SMIP shows specific affinity to 2,4-D and reversible uptake and release of 2,4-D upon alternate irradiation at 365 and 440 nm, respectively. The favorable binding strength of the imprinted receptor sites in the SMIP for 2,4-D is found to be 2.51 × 104 M−1. Density of receptor sites in the SMIP material is 10.59 μmol/g SMIP. The SMIP requires a shorter time to reach equilibrium than does the conventional molecularly imprinted polymer. The well-defined core-shell structure was clearly visualized by high resolution transmission electron microscopy.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Analytical chemistry methods development · Analytical Chemistry and Sensors · Luminescence and Fluorescent Materials
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References (29)
Show source-provided references
1. Kumpfer JR, Rowan SJ (2011) Thermo-, photo-, and chemo-responsive shape-memory properties from photo-cross-linked metallo-supramolecular polymers. J Am Chem Soc 132:12866–1287410.1021/ja205332w ↗
2. Diaz DD, Kuhbeck D, Koopmans RJ (2011) Stimuli-responsive gels as reaction vessels and reusable catalysts. Chem Soc Rev 40:427–44810.1039/C005401C ↗
3. Aznar E, Marcos MD, Martinez–Manez R, Sancenon F, Soto J, Amoros P, Guillem C (2009) pH- and photo-switched release of guest molecules from mesoporous silica supports. J Am Chem Soc 131:6833–684310.1021/ja810011p ↗
4. Nandivada H, Ross AM, Lahann L (2010) Stimuli-responsive monolayers for biotechnology. Prog Polym Sci 35:141–15410.1016/j.progpolymsci.2009.11.001 ↗
5. Kanazawa H (2007) Thermally responsive chromatographic materials using functional polymers. J Sep Sci 30:1646–165610.1002/jssc.200700093 ↗
6. Teng MJ, Kuang GC, Jia XR, Gao M, Li Y, Wei Y (2009) Glycine-glutamic-acid-based organogelators and their fluoride anion responsive properties. J Mater Chem 19:5648–565410.1039/b904263f ↗
7. Tang Q, Gong CB, Lam MHW, Fu XK (2011) Preparation of a photoresponsive molecularly imprinted polymer containing fluorine-substituted azobenzene chromophores. Sens Actuators B Chem 156:100–10710.1016/j.snb.2011.03.078 ↗
8. Gong CB, Wong KL, Lam MHW (2008) Photoresponsive molecularly imprinted hydrogels for the photoregulated release and uptake of pharmaceuticals in the aqueous media. Chem Mater 20:1353–135810.1021/cm7019526 ↗
9. Gong CB, Lam MHW, Yu HX (2006) The fabrication of a photoresponsive molecularly imprinted polymer for the photoregulated uptake and release of caffeine. Adv Funct Mater 16:1759–176710.1002/adfm.200500907 ↗
10. Jiang GS, Zhong SA, Chen L, Blakey I, Whitaker A (2011) Synthesis of molecularly imprinted organic-inorganic hybrid azobenzene materials by sol–gel for radiation induced selective recognition of 2,4-dichlorophenoxyacetic acid. Radiat Phys Chem 80:130–13510.1016/j.radphyschem.2010.07.020 ↗
11. Tang Q, Gong CB, Lam MHW, Fu XK (2011) Photoregulated uptake and release of drug by an organic–inorganic hybrid sol–gel material. J Sol Gel Sci Technol 59:495–50410.1007/s10971-011-2518-4 ↗
12. Shea KJ, Yan M, Roberts MJ (2002) Molecularly imprinted materials—sensors and other devices. Materials Research Society, Warrendale
13. He MQ, Song CC, Yan YS, Chen YQ, Wan JC (2011) Synthesis and recognition of molecularly imprinted polymers for gastrodin based on surface-modified silica nanoparticles. J Appl Polym Sci 121:2354–236010.1002/app.33887 ↗
14. Gao DM, Zhang ZP, Wu MH, Xie CG, Guan GJ, Wang DP (2007) A surface functional monomer-directing strategy for highly dense imprinting of TNT at surface of silica nanoparticles. J Am Chem Soc 129:7859–786610.1021/ja070975k ↗
15. Aulakh JS, Malik AK, Kaur V, Schmitt-Kopplin P (2005) A review on solid phase micro extraction-high performance liquid chromatography (SPME-HPLC) analysis of pesticides. Crit Rev Anal Chem 35:71–8510.1080/10408340590947952 ↗
16. Fries E (2011) Determination of benzothiazole in untreated wastewater using polar-phase stir bar sorptive extraction and gas chromatography mass spectrometry. Anal Chim Acta 689:65–6810.1016/j.aca.2011.01.015 ↗
17. Lambropoulou DA, Albanis TA (2007) Methods of sample preparation for determination of pesticide residues in food matrices by chromatography-mass spectrometry-based techniques: a review. Anal Bioanal Chem 389:1663–168310.1007/s00216-007-1348-2 ↗
18. Gabaldon JA, Maquieira A, Puchades R (2007) Development of a simple extraction procedure for chlorpyrifos determination in food samples by immunoassay. Talanta 71:1001–101010.1016/j.talanta.2006.04.041 ↗
19. Yun YH, Shon HK, Yoon SD (2009) Preparation and characterization of molecularly imprinted polymers for the selective separation of 2,4-dichlorophenoxyacetic acid. J Mater Sci 44:6206–621110.1007/s10853-009-3863-3 ↗
20. Legido-Quigley C, Oxelbark J, De Lorenzi E, Zurutuza-Elorza A, Cormack PAG (2007) Chromatographic characterisation, under highly aqueous conditions, of a molecularly imprinted polymer binding the herbicide 2,4-dichlorophenoxyacetic acid. Anal Chim Acta 591:22–2810.1016/j.aca.2007.01.022 ↗
21. Kumar GS, Neckers DC (1989) Photochemistry of azobenzene-containing polymers. Chem Rev 89:1915–192510.1021/cr00098a012 ↗
22. Tang Q, Nie YT, Gong CB, Chow CF, Peng JD, Lam MHW (2012) Photo-responsive molecularly imprinted hydrogels for the detection of melamine in aqueous media. J Mater Chem 22:19812–1982010.1039/c2jm34522f ↗
23. Babu RR, Kumaresan S, Vijayan N, Gunasekaran M, Gopalakrishnan R, Kannan P, Ramasamy P (2003) Growth of 4,4′-dihydroxyazobenzene (DHAB) and its characterization. J Cryst Growth 256:387–39210.1016/S0022-0248(03)01369-1 ↗
24. Stöber W, Fink A, Bohn E (1968) Controlled growth of monodisperse silica spheres in the micron size range. J Colloid Interface Sci 26:62–6910.1016/0021-9797(68)90272-5 ↗
25. Tang Q, Meng XZ, Jiang HB, Zhou TY, Gong CB, Fu XK, Shi SQ (2010) Synthesis and characterization of photo- and pH-responsive nanoparticles containing amino-substituted azobenzene. J Mater Chem 20:9133–913910.1039/c0jm01235a ↗
26. Fang LJ, Chen SJ, Zhang Y, Zhang HQ (2011) Azobenzene-containing molecularly imprinted polymer microspheres with photoresponsive template binding properties. J Mater Chem 21:2320–232910.1039/C0JM02898C ↗
27. Peng Y, Xie Y, Luo J, Nie L, Chen Y, Chen LN, Du SH, Zhang ZP (2010) Molecularly imprinted polymer layer-coated silica nanoparticles toward dispersive solid-phase extraction of trace sulfonylurea herbicides from soil and crop samples. Anal Chim Acta 674:190–20010.1016/j.aca.2010.06.022 ↗
28. Wang S, Li Y, Wu XL, Ding MJ, Yuan LH, Wang RY, Wen TT, Zhang J, Chen LN, Zhou XM, Li F (2011) Construction of uniformly sized pseudo template imprinted polymers coupled with HPLC-UV for the selective extraction and determination of trace estrogens in chicken tissue samples. J Hazard Mater 186:1513–151910.1016/j.jhazmat.2010.12.026 ↗
29. Ma J, Yuan LH, Ding MJ, Wang S, Ren F, Zhang J, Du SH, Li F, Zhou XM (2011) The study of core-shell molecularly imprinted polymers of 17 beta-estradiol on the surface of silica nanoparticles. Biosens Bioelectron 26:2791–279510.1016/j.bios.2010.10.045 ↗