Abstract
Three candidate monomers (methacrylic acid, 2-vinyl pyridine, and 2-acrylamide-2-methyl sulfuric acid) were screened through computational simulation method to prepare effective surface molecularly imprinted polymers (SMIPs) based on carbon microspheres (CMSs) for dibenzothiophene removal from fuels. The optimized structures of complexes were described using density functional theory calculation at B3LYP/6-311++G(d,p) level and frequency calculations for each molecule and complex were conducted to provide insights into electrostatic interaction between monomers and template DBT. Besides, the reliability of computational simulation method for screening was tested by comparing the theoretical data with experimental results from gas chromatography. The computational data suggest that methacrylic acid (MAA) was the preferred monomer with the largest absolute binding energy (14.79 kJ mol−1), which is in accordance with the experimental results. The saturated adsorption of PMAA-SMIPs/CMSs was the best (41.73 mg g−1). Besides, PMAA-SMIPs/CMSs show highest special selectivity for dibenzothiophene against benzothiophene, and the relative selectivity coefficient k′ was 2.02. The computational simulation method can be effectively used in monomer screening. This work may help understand the mechanisms of polymerization and recognition process between SMIPs and template and design SMIPs with improved adsorption performance.
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References
Ania CO, Bandosz TJ (2005) Langmuir 21:7752
Seredych M, Wu CT, Brender P, Ania CO, Vix-Guterl C, Bandosz TJ (2012) Fuel 92:318
Tao H, Nakazato T, Sato S (2009) Fuel 88:1961
Zhang J, Wang AJ, Li X, Ma Xuehu (2011) J Catal 279:269
Yu C, Fan XM, Yu LM, Bandosz T, Zhao ZB, Qiu JS (2013) Energy Fuels 27:1499
Xu X, Shen XP, Zhu GX, Jing LQ, Liu XS, Chen KM (2012) Chem Eng J 200:521
Seredych M, Bandosz TJ (2010) Energy Fuels 24:3352
Asumana C, Yu GR, Li X, Zhao JJ, Liu G, Chen XC (2010) Green Chem 12:2030
Davoodi-Dehaghani F, Vosoughi M, Ziaee AA (2010) Bioresour Technol 101:1102
Dinamarca MA, Ibacache-Quiroga C, Baeza P, Galvez S, Villarroel M, Olivero P, Ojeda J (2010) Bioresour Technol 101:2375
Byrne ME, Salian V (2008) Int J Pharm 364:188
Castro B, Whitcombe MJ, Vulfson EN, Vazquez-Duhalt R, Barzana E (2001) Anal Chim Acta 435:83
Haupt K, Mosbach K (2000) Chem Rev 100:2495
Yang YZ, Liu XG, Guo MC, Li S, Liu WF, Xu BS (2011) Colloids Surf A 377:379
Shen X, Zhu L, Wang N, Ye L, Tang H (2012) Chem Commun 48:788
Chen LX, Xu SF, Li JH (2011) Chem Soc Rev 40:2922
Mathew-Krotz J, Shea KJ (1996) J Am Chem Soc 118:8154
Gao BJ, Wang J, An FQ, Liu Q (2008) Polymer 49:1230
Lee HY, Kim BS (2009) Biosens Bioelectron 25:587
Zhao WH, Sheng N, Zhu R (2010) J Hazard Mater 179:223
Chi WH, Shi HG, Shi W, Guo Y, Guo TY (2012) J Hazard Mater 227–228:243
Xie CG, Zhang ZP, Wang DP, Guan GJ, Gao DM, Liu JH (2006) Anal Chem 78:8339
Hu TP, Zhang YM, Zheng LH (2010) J Fuel Chem Technol 38:722
Xu WZ, Zhou W, Xu PP, Yan YS, Wu XY (2011) Chem Eng J 172:191
Duan FF, Chen CQ, Wang GZ, Yang YZ, Liu XG, Qin Y (2014) RSC Adv 4:1469
Morishita T, Matsushita M, Katagiri Y (2009) Carbon 11:2716
Serp P, Feurer R, Kalck P (2001) Carbon 39:621
Liu WF, Liu XG, Yang YZ, Zhang Y, Xu B (2014) Fuel 117:184
Zeng H, Wang YZ, Liu XJ, Kong JH, Nie C (2012) Talanta 93:172
Nicholls IA, Adbo K, Andersson HS, Andersson PO, Hedin-Dahlstrom J, Jokela P, Karlsson JG, Olofeeon L, Rosengren J, Shoravi S, Svenson J, Wikman S (2001) Anal Chim Acta 435:9
Karim K, Breton F, Rouillon R, Piletska EV, Guerreiro A, Chianella I, Piletsky (2005) Adv Drug Delivery Rev 57:1795
Yong YZ, Zhang Y, Li S, Liu XG, Xu BS (2012) Appl Surf Sci 258:6441
Yao JH, Li X, Qin W (2008) Anal Chim Acta 610:282
Dong C, Li X, Guo Z, Oi J (2009) Anal Chim Acta 647:117
Li P, Rong F, Zhu XL, Hu RJ, Yuang CW (2003) Acta Polym Sin 724
Farrington K, Regan F (2007) Biosens Bioelectron 22:1138
Su LQ, Zhang XL, Liang YK (2009) Chemistry 749
Saloni J, Lipkowski P, Dasary SR (2011) Polymer 52:1206
Prasad BB, Rai G (2012) Spectrochim Acta A 88:82
Lee SY (2001) J Phys Chem A 105:8093
Niu XQ, Zhang JG, Feng XJ, Chen PW, Zhang TL, Wang SY, Zhang SW, Zhou ZN, Yang L (2011) Acta Chim Sin 69:1627
Cheng WJ, Liu ZJ, Wang Y (2013) Talanta 116:396
Acknowledgments
We are grateful to National Natural Science Foundation of China (21176169), Shanxi Provincial Key Innovative Research Team in Science and Technology (2012041011), International Science and Technology Cooperation Program of China (2012DFR50460) and Shanxi Scholarship Council of China (2012-038) for financial support.
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Qin, L., Liu, W., Yang, Y. et al. Functional monomer screening and preparation of dibenzothiophene-imprinted polymers on the surface of carbon microsphere. Monatsh Chem 146, 449–458 (2015). https://doi.org/10.1007/s00706-014-1311-9
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DOI: https://doi.org/10.1007/s00706-014-1311-9