Citation: CHEN Ying, ZHANG Qi, LIANG Hong-bao, TIAN Gong-wei, LI Jing. Preparation and properties of dibenzothiophene molecularly imprinted functionalized MOF199 adsorbent[J]. Journal of Fuel Chemistry and Technology, ;2018, 46(9): 1130-1136. shu

Preparation and properties of dibenzothiophene molecularly imprinted functionalized MOF199 adsorbent

  • Corresponding author: CHEN Ying, chenying648617@163.com
  • Received Date: 4 May 2018
    Revised Date: 13 July 2018

    Fund Project: the National Natural Science Foundation of China 21463006The project was supported by the National Natural Science Foundation of China(21463006)

Figures(5)

  • Combined with molecular imprinting technology, a novel surface molecularly imprinted polymer material MOF@SMIP was prepared, using MOF199 used as matrix, dibenzothiophene (DBT) as template molecule and methacrylic acid (MAA) as functional monomer. The structure and morphology were characterized by SEM, BET, FT-IR, etc. The adsorption behavior was evaluated using a simulated oil sample. The adsorption equilibrium time was 1.5 h. The MOF@SMIP adsorption capacity for DBT (130.73 mg/g) was higher than that for the MOF199 (37.79 mg/g), while the MOF@SMIP adsorption capacity (57.13 mg/g) was comparable to the MOF@NIP adsorption capacity. The obvious advantage is that the imprint factor fimp is 2.29. Adsorption behavior follows the pseudo-first-order kinetic model, indicating that the adsorption is primarily a physical process. The selective adsorption experiments showed that the MOF@SMIP exhibited a higher affinity for the target molecule DBT than the structural analog benzothiophene (BT) and biphenyl. The relative selection coefficient k' of the adsorbed DBT to the interferent BT and biphenyl was 2.55 and 2.14, respectively.
  • 加载中
    1. [1]

      HU Ting-ping, ZHANG Yan-ming, ZHENG Li-hui, FAN Guo-zhi. Molecular recognition and adsorption properties of benzothiophene molecularly imprinted polymers on silica gel surface[J]. J Fuel Chem Technol, 2010,38(6):722-729. doi: 10.3969/j.issn.0253-2409.2010.06.016

    2. [2]

      CHEN L, XU S, LI J. Recent advances in molecular imprinting technology:Current status, challenges and highlighted applications[J]. Chem Soc Rev, 2011,40(5):2922-2942. doi: 10.1039/c0cs00084a

    3. [3]

      YANG Y Z, LIU X G, XU B S. Recent advances in molecular imprinting technology for the deep desulfurization of fuel oils[J]. New Carbon Mater, 2014,29(1):1-14. doi: 10.1016/S1872-5805(14)60121-9

    4. [4]

      MEHRZAD-SAMARIN M, FARIDBOD F, DEZFULI A S, GANJALI M R. A novel metronidazole fluorescent nanosensor based on graphene quantum dots embedded silica molecularly imprinted polymer[J]. Biosens Bioelectron, 2017,92:618-623. doi: 10.1016/j.bios.2016.10.047

    5. [5]

      CHANUT N, BOURRELLY S, KUCHTA B, SERRE C, CHANG J S, WRIGHT P A, LLEWELLYN P L. Screening the effect of water vapour on gas adsorption performance:Application to CO2 capture from flue gas in metal-organic frameworks[J]. ChemSusChem, 2017,10(7):1543-1553. doi: 10.1002/cssc.v10.7

    6. [6]

      CHOWDHUR Y, MOHAMMAD A. Metal-organic-frameworks for biomedical applications in drug delivery, and as MRI contrast agents[J]. J Biomed Mater Res A, 2017,105(4):1184-1194. doi: 10.1002/jbm.v105.4

    7. [7]

      PAN H, ZHANG P, GAO D, ZHANG Y, LI P, LIU L, CAI L. Noninvasive visualization of respiratory viral infection usingbioorthogonal conjugated near-infrared-emitting quantum dots[J]. ACS Nano, 2014,8(6):5468-5477. doi: 10.1021/nn501028b

    8. [8]

      ZHAO S N, SONG X Z, SONG S Y, ZHANG H J. Highly efficient heterogeneous catalytic materials derived from metal-organic framework supports/precursors[J]. Coordin Chem Rev, 2017,337:80-96. doi: 10.1016/j.ccr.2017.02.010

    9. [9]

      XU Y, YIN X B, HE X W, ZHANG Y K. Electrochemistry and electrochemiluminescence from a redox-active metal-organic framework[J]. Biosens Bioelectron, 2015,68:197-203. doi: 10.1016/j.bios.2014.12.031

    10. [10]

      BOUGRINI M, FLOREA A, CRISTEA C, SANDULESCU R, VOCANSON F, ERRACHID A, JAFFREZIC-RENAULT N. Development of a novel sensitive molecularly imprinted polymer sensor based on electropolymerization of a microporous-metal-organic framework for tetracycline detection in honey[J]. Food Control, 2016,59:424-429. doi: 10.1016/j.foodcont.2015.06.002

    11. [11]

      GUO Z, FLOREA A, CRISTEA C, BESSUEILLE F, VOCANSON F, GOUTALAND F, JAFFREZIC-RENAULT N. 1, 3, 5-Trinitrotoluene detection by a molecularly imprinted polymer sensor based on electropolymerization of a microporous-metal-organic framework[J]. Sensor Actuat B:Chem, 2015,207:960-966. doi: 10.1016/j.snb.2014.06.137

    12. [12]

      NGUYEN L T L, NGUYEN T T, NGUYEN K D, PHAN N T. Metal-organic framework MOF-199 as an efficient heterogeneous catalyst for the aza-Michael reaction[J]. Appl Catal A:Gen, 2012,425:44-52.  

    13. [13]

      WANG Xiao-jing, LIU Chao, DONG Yue, LI Fa-tang, ZHAO Jun, LI Yu-pei. Preparation of activated carbon modified by tetrafluoroboric acid and its adsorptive removal of dibenzothiophene[J]. J Fuel Chem Technol, 2015,43(5):607-613. doi: 10.3969/j.issn.0253-2409.2015.05.013 

    14. [14]

      YUAN Z, LIU Y, AN F. Preparation and phenol-recognizing ability of a poly (methacrylic acid) molecular imprint on the surface of a silica gel[J]. Microchim Acta, 2011,172(1/2):89-94.  

    15. [15]

      LI H, XU M, WANG S, LU C, LI Z. Preparation, characterization and selective recognition for vanillic acid imprinted mesoporous silica polymers[J]. Appl Surf Sci, 2015,328:649-657. doi: 10.1016/j.apsusc.2014.12.085

    16. [16]

      LIU W, QIN L, SHI W, CHEN L, YANG Y, LIU X, XU B. Molecularly imprinted polymers on the surface of porous carbon microspheres for capturing dibenzothiophene[J]. Microchim Acta, 2016,183(3):1153-1160. doi: 10.1007/s00604-016-1746-2

    17. [17]

      COLLET F, BART M, SERRES L, MIRIEL J. Porous structure and water vapour sorption of hemp-based materials[J]. Constr Build Mater, 2008,22(6):1271-1280. doi: 10.1016/j.conbuildmat.2007.01.018

    18. [18]

      ZHANG L, YANG L, JELLE B P, WANG Y, GUSTAVSEN A. Hygrothermal properties of compressed earthen bricks[J]. Constr Build Mater, 2018,162:576-583. doi: 10.1016/j.conbuildmat.2017.11.163

    19. [19]

      QIN L, SHI W, LIU W, YANG Y, LIU X, XU B. Surface molecularly imprinted polymers grafted on ordered mesoporous carbon nanospheres for fuel desulfurization[J]. RSC Adv, 2016,6(15):12504-12513. doi: 10.1039/C5RA23582K

    20. [20]

      KHAN N A, JHUNG S H. Adsorptive removal and separation of chemicals with metal-organic frameworks:Contribution of π-complexation[J]. J Hazard Mater, 2017,325:198-213. doi: 10.1016/j.jhazmat.2016.11.070

    21. [21]

      LEE K X, VALLA J A. Investigation of metal-exchanged mesoporous Y zeolites for the adsorptive desulfurization of liquid fuels[J]. Appl Catal B:Environ, 2017,201:359-369. doi: 10.1016/j.apcatb.2016.08.018

    22. [22]

      YANG Y, LIU X, GUO M, LI S, LIU W, XU B. Molecularly imprinted polymer on carbon microsphere surfaces for adsorbing dibenzothiophene[J]. Colloid Surface A, 2011,377(1):379-385.  

    23. [23]

      XU W, ZHOU W, XU P P, PAN J M, WU X Y, YAN Y S. A molecularly imprinted polymer based on TiO2 as a sacrificial support for selective recognition of dibenzothiophene[J]. Chem Eng J, 2011,172(1):191-198. doi: 10.1016/j.cej.2011.05.089

    24. [24]

      YANG W, ZHOU W, XU W, LI H, HUANG W, JIANG B, YAN Y. Synthesis and characterization of a surface molecular imprinted polymer as a new adsorbent for the removal of dibenzothiophene[J]. J Chem Eng Data, 2012,57(6):1713-1720. doi: 10.1021/je201380m

    25. [25]

      ZUHLKE C A, ANDERSON T P, ALEXANDER D R. Formation of multiscale surface structures on nickel via above surface growth and below surface growth mechanisms using femtosecond laser pulses[J]. Opt Express, 2013,21(7):8460-8473. doi: 10.1364/OE.21.008460

    26. [26]

      YANG W, LIU L, ZHOU Z, LIU H, XIE B, XU W. Rational preparation of dibenzothiophene-imprinted polymers by surface imprinting technique combined with atom transfer radical polymerization[J]. Appl Surf Sci, 2013,282:809-819. doi: 10.1016/j.apsusc.2013.06.063

    27. [27]

      LI Q, YANG K, LIANG Y, JIANG B, LIU J, ZHANG L, ZHANG Y. Surface protein imprinted core-shell particles for high selective lysozyme recognition prepared by reversible addition-fragmentation chain transfer strategy[J]. Acs Appl Mater Inter, 2014,6(24):21954-21960. doi: 10.1021/am5072783

    28. [28]

      HUANG R, LIU Q, HUO J, YANG B. Adsorption of methyl orange onto protonated cross-linked chitosan[J]. Arab J Chem, 2017,10(1):24-32. doi: 10.1016/j.arabjc.2013.05.017

    29. [29]

      LIU W, QIN L, YANG Y, LIU X, XU B. Synthesis and characterization of dibenzothiophene imprinted polymers on the surface of iniferter-modified carbon microspheres[J]. Mater Chem Phys, 2014,148(3):605-613. doi: 10.1016/j.matchemphys.2014.08.024

    30. [30]

      ZHANG M, HUANG J, YU P, CHEN X. Preparation and characteristics of protein molecularly imprinted membranes on the surface of multiwalled carbon nanotubes[J]. Talanta, 2010,81(1):162-166.  

    31. [31]

      YU C, FAN X, YU L, BANDOSZ T J, ZHAO Z, QIU J. Adsorptive removal of thiophenic compounds from oils by activated carbon modified with concentrated nitric acid[J]. Energy Fuels, 2013,27(3):1499-1505. doi: 10.1021/ef400029b

  • 加载中
    1. [1]

      Malaika Arshad ,  Zia Ul Haq Khan ,  Swera Talib ,  Sana Sabahat ,  Noor Samad Shah ,  Huma Ajab ,  Farooq Ahmad ,  Syed Khasim ,  M. A. Diab ,  Heba A. El-Sabban . A comprehensive review: MOFs and their derivatives as high-performance supercapacitor electrodes. Chinese Journal of Structural Chemistry, 2025, 44(9): 100676-100676. doi: 10.1016/j.cjsc.2025.100676

    2. [2]

      Fei Jin ,  Bolin Yang ,  Xuanpu Wang ,  Teng Li ,  Noritatsu Tsubaki ,  Zhiliang Jin . Facilitating efficient photocatalytic hydrogen evolution via enhanced carrier migration at MOF-on-MOF S-scheme heterojunction interfaces through a graphdiyne (CnH2n-2) electron transport layer. Chinese Journal of Structural Chemistry, 2023, 42(12): 100198-100198. doi: 10.1016/j.cjsc.2023.100198

    3. [3]

      Guoqiang Peng , Xiuyan Li , Min Li , Zhibo Su , Falu Hu , Guowei Zhou . Engineering efficient metal-organic frameworks for photocatalytic CO2 reduction. Acta Physico-Chimica Sinica, 2026, 42(2): 100164-0. doi: 10.1016/j.actphy.2025.100164

    4. [4]

      Xufei Li ,  Junfa Fu ,  Weiqiu Huang ,  Zhaoqiang Zhang ,  Xiaofang Lv ,  Jiahao Kang ,  Jixing Xu ,  Jiahua Cheng ,  Yuhao Lu ,  Yitong Sun . Modification of open metal sites in metal-organic frameworks for the enhancement of CO2 capture and alkane separation. Chinese Journal of Structural Chemistry, 2026, 45(6): 100892-100892. doi: 10.1016/j.cjsc.2026.100892

    5. [5]

      Brij Mohan ,  Ismayil M. Garazade ,  Khayala Seyidova ,  Matlab Khamiyev ,  M. Fátima C. Guedes da Silva ,  Armando J. L. Pombeiro ,  Wei Sun . Structure-function relationships in metal-ligand coordination sensors for metal-ion detection. Chinese Journal of Structural Chemistry, 2026, 45(9): 100972-100972. doi: 10.1016/j.cjsc.2026.100972

    6. [6]

      Wenting Wu , Zhao Chen , Man Zhe , Peiyun Yu , Sujan Shakya , Fei Xing , Ulrike Ritz . Engineered stimuli-responsive MOFs: Toward intelligent drug delivery systems for precision biomedicine. Chinese Chemical Letters, 2026, 37(6): 111448-. doi: 10.1016/j.cclet.2025.111448

    7. [7]

      Sida Huang , Shihai Yin , Aparna Kushwaha , Abhinav Kumar , Yu Deng , Yanqiong Peng , Ying Pan , Jianqiang Liu , Yong Huang . MOFs-based nanomaterials for bone repair and regeneration: Current status and future perspectives. Chinese Chemical Letters, 2026, 37(8): 111211-. doi: 10.1016/j.cclet.2025.111211

    8. [8]

      Yaowen Liu , Xu Zhu , Zijian Chen , Beichen Xue , Haitao Yi , Xin Huang , Yilin Ji , Jing Li , Xingqi Han , Xinlong Tian . Defect-rich MOFs with multiple adsorption and catalytic sites for efficient electrochemical uranium extraction from seawater. Chinese Chemical Letters, 2026, 37(12): 112892-. doi: 10.1016/j.cclet.2026.112892

    9. [9]

      Yaxin Sun , Huiyu Li , Shiquan Guo , Congju Li . Metal-based cathode catalysts for electrocatalytic ORR in microbial fuel cells: A review. Chinese Chemical Letters, 2024, 35(5): 109418-. doi: 10.1016/j.cclet.2023.109418

    10. [10]

      Fei Yin , Erli Yang , Xue Ge , Qian Sun , Fan Mo , Guoqiu Wu , Yanfei Shen . Coupling WO3−x dots-encapsulated metal-organic frameworks and template-free branched polymerization for dual signal-amplified electrochemiluminescence biosensing. Chinese Chemical Letters, 2024, 35(4): 108753-. doi: 10.1016/j.cclet.2023.108753

    11. [11]

      Erzhuo Cheng , Yunyi Li , Wei Yuan , Wei Gong , Yanjun Cai , Yuan Gu , Yong Jiang , Yu Chen , Jingxi Zhang , Guangquan Mo , Bin Yang . Galvanostatic method assembled ZIFs nanostructure as novel nanozyme for the glucose oxidation and biosensing. Chinese Chemical Letters, 2024, 35(9): 109386-. doi: 10.1016/j.cclet.2023.109386

    12. [12]

      Shenghui Tu , Anru Liu , Hongxiang Zhang , Lu Sun , Minghui Luo , Shan Huang , Ting Huang , Honggen Peng . Oxygen vacancy regulating transition mode of MIL-125 to facilitate singlet oxygen generation for photocatalytic degradation of antibiotics. Chinese Chemical Letters, 2024, 35(12): 109761-. doi: 10.1016/j.cclet.2024.109761

    13. [13]

      Ying Zhao , Yin-Hang Chai , Meng-Meng Zhai , Qin-Ying Jin , Xiaoyan Lu , Yi-Dan Qiao , Lu-Fang Ma . New functional metal–organic framework (MOF) based optical thermometer by the post-synthesis doping rare earth ions into MOF. Chinese Chemical Letters, 2026, 37(1): 111085-. doi: 10.1016/j.cclet.2025.111085

    14. [14]

      Zhemi Xu , Haolin Cui , Shule Zhang , Peiyuan Guan , Tianhao Ji , Jin Yan , Qianyu Li , Dewei Chu , Yunxuan Weng , Zhimin Ao , Yang Liu , Jian Jin . Facet engineering of metal-organic frameworks enables high piezoelectricity and piezocatalysis: A case study of ZIF-8. Chinese Chemical Letters, 2026, 37(4): 111667-. doi: 10.1016/j.cclet.2025.111667

    15. [15]

      Lingxiang Bao , Jing-Hong Li , Rui-Biao Lin , Jianyuan Wu , Zhenhong Tan , Wu Xie , Wenhai Ji , Dong Zhang , Anucha Koedtruad , Jingjing Ma , Wang Hay Kan , Feng Pan , Toru Ishigaki , Takashi Kamiyama , Ping Miao . Elucidation of the CO2 adsorption mechanism of [Zn2(mtz)2(ox)] using neutron powder diffraction. Chinese Chemical Letters, 2026, 37(5): 110864-. doi: 10.1016/j.cclet.2025.110864

    16. [16]

      Shiyu Wei , Xiang Li , Chao Huang , Dongmei Chen , Shunlin Zhang , Bixue Zhu . Enhanced PFOA removal via defect engineering in NH2-UiO-66. Chinese Chemical Letters, 2026, 37(5): 111858-. doi: 10.1016/j.cclet.2025.111858

    17. [17]

      Qingkun Zhu , Yaodong Jin , Bao Zhang , Wei Liu , Haozhe Qin , Lei Ming , Xing Ou . Engineering a triplex ionic transport architecture for high ionic conductivity in solid-state lithium metal batteries. Chinese Chemical Letters, 2026, 37(8): 111411-. doi: 10.1016/j.cclet.2025.111411

    18. [18]

      Zhe Ji ,  Guangxu Lan ,  Jiangnan Li ,  Sihai Yang . A New Protocol to Construct Molecular Materials: A Brief Introduction on the 2025 Nobel Prize in Chemistry. University Chemistry, 2025, 40(12): 70-77. doi: 10.12461/PKU.DXHX202511097

    19. [19]

      Yuxia Luo ,  Xiaoyu Xie ,  Fangfang Chen . 药物递送魔法师——分子印迹聚合物. University Chemistry, 2025, 40(8): 202-210. doi: 10.12461/PKU.DXHX202409129

    20. [20]

      Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-0. doi: 10.3866/PKU.WHXB202309027

Metrics
  • PDF Downloads(11)
  • Abstract views(1707)
  • HTML views(192)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return