Highly structured, molecularly imprinted polymer (MIP) networks for copper(II) ion sequestration have been realized using the additive manufacturing technology. Photopolymerizable formulations with acrylic functional monomers and two different porogens (water and methanol) in different ratios were studied to produce emulsions with 50 vol% of the internal phase. The results of morphological characterization indicate that all MIPs have cauliflower-like multiscale structures that change as a function of the solvent combination and fabrication process. X-ray fluorescence microscopy maps presented a layered structure and homogeneous distribution of copper in the printed MIP. Copper(II) ion adsorption–desorption tests were performed on MIPs prepared using a three-dimensional (3D) printing approach and MIPs prepared by bulk polymerization. Results indicate that the 3D printed MIP is able to absorb copper up to ten times more efficiently than the nonprinted one and the printed MIP with 100% water content has the highest imprint recognition.
Get full access to this article
View all access options for this article.
References
1.
EkbergB, MosbachK. Molecular imprinting: A technique for producing specific separation materials. Trends Biotechnol, 1989; 7:92–96.
2.
AlexanderC, AnderssonHS, AnderssonLI, et al.Molecular imprinting science and technology: A survey of the literature for the years up to and including 2003. J Mol Recognit, 2006; 19:106–180.
3.
ZhouT, DingL, CheG, et al.Recent advances and trends of molecularly imprinted polymers for specific recognition in aqueous matrix: Preparation and application in sample pretreatment. TrAC Trends Anal Chem, 2019; 114:11–28.
4.
PupinRR, MonteiroGC, FoguelMV, et al. Molecularly imprinted polymers (MIP): From the bulk synthesis to hybrid material to classic and new applications. In: Quinn T, ed. Molecularly Imprinted Polymers (MIPs): Challenges, Uses and Prospects. NY, USA: Nova Science Publishers, Inc., 2017. pp. 43–118.
5.
PetcuM, KarlssonJG, WhitcombeMJ, et al.Probing the limits of molecular imprinting: Strategies with a template of limited size and functionality. J Mol Recognit, 2009; 22:18–25.
6.
Ortiz-PalaciosJ, CardosoJ, ManeroO. Production of macroporous resins for heavy-metal removal. I. Nonfunctionalized polymers. J Appl Polym Sci, 2008; 107:2203–2210.
7.
SongZ, LiJ, LuW, et al.Molecularly imprinted polymers based materials and their applications in chromatographic and electrophoretic separations. TrAC Trends Anal Chem, 2022; 146:116504.
8.
SuwanwongY, BoonpangrakS. Molecularly imprinted polymers for the extraction and determination of water-soluble vitamins: A review from 2001 to 2020. Eur Polym J, 2021; 161:110835.
9.
ChoiJR, YongKW, ChoiJY, et al.Progress in molecularly imprinted polymers for biomedical applications. Comb Chem High Throughput Screen, 2019; 22:78–88.
10.
AhmadOS, BedwellTS, EsenC, et al.Molecularly imprinted polymers in electrochemical and optical sensors. Trends Biotechnol, 2019; 37:294–309.
11.
AfsarimaneshN, MukhopadhyaySC, KrugerM. MIP-Based Sensor for CTx-I Detection. In: AfsarimaneshN, MukhopadhyaySC, KrugerM, eds. Electrochemical Biosensor: Point-of-Care for Early Detection of Bone Loss. Cham: Springer International Publishing, 2019. pp. 59–91.
12.
ParisiOI, FrancomanoF, DattiloM, et al.The evolution of molecular recognition: From antibodies to molecularly imprinted polymers (MIPs) as artificial counterpart. J Funct Biomater. 2022; 13:12.
13.
YeginY, YilmazG, Karakoç Ö, et al. Molecularly imprinted materials for controlled release systems. Adv Mol Imprint Mater, 2016; 453–522.
14.
BouvarelT, DelaunayN, PichonV. Molecularly imprinted polymers in miniaturized extraction and separation devices. J Sep Sci, 2021; 44:1727–1751.
15.
TrakulsujaritchokT, NoiphomN, TangtreamjitmunN, et al.Adsorptive features of poly(glycidyl methacrylate-co-hydroxyethyl methacrylate): Effect of porogen formulation on heavy metal ion adsorption. J Mater Sci, 2011; 46:5350–5362.
16.
RahmanSKA, YusofNA, AbdullahAH, et al.Evaluation of porogen factors for the preparation of ion imprinted polymer monoliths used in mercury removal. PLoS One, 2018; 13:e0195546.
17.
AziziA, BottaroCS. A critical review of molecularly imprinted polymers for the analysis of organic pollutants in environmental water samples. J Chromatogr A, 2020; 1614:460603.
18.
LiuY, LianZ, LiF, et al.Review on molecular imprinting technology and its application in pre-treatment and detection of marine organic pollutants. Marine Pollut Bull, 2021; 169:112541.
19.
Erdem Ö, SaylanY, AndaçM, et al.Molecularly imprinted polymers for removal of metal ions: An alternative treatment method. Biomimetics (Basel). 2018; 3:38.
20.
FuJ, ChenL, LiJ, et al.Current status and challenges of ion imprinting. J Mater Chem A, 2015; 3:13598–13627.
21.
RahangdaleD, KumarA, ArchanaG, et al.Ion cum molecularly dual imprinted polymer for simultaneous removal of cadmium and salicylic acid. J Mol Recogn, 2018; 31:e2630.
22.
ConradPG, NishimuraPT, AherneD, et al.Functional molecularly imprinted polymer microstructures fabricated using microstereolithography. Adv Mater, 2003; 15:1541–1544.
23.
GomezLPC, SpangenbergA, TonX-A, et al.Rapid prototyping of chemical microsensors based on molecularly imprinted polymers synthesized by two-photon stereolithography. Adv Mater, 2016; 28:5931–5937.
24.
SantosH, MartinsRO, SoaresDA, et al.Molecularly imprinted polymers for miniaturized sample preparation techniques: Strategies for chromatographic and mass spectrometry methods. Anal Methods, 2020; 12:894–911.
25.
ForchheimerD, LuoG, MonteliusL, et al.Molecularly imprinted nanostructures by nanoimprint lithography. Analyst, 2010; 135:1219–1223.
26.
FeeC, NawadaS, DimartinoS. 3D printed porous media columns with fine control of column packing morphology. J Chromatogr A, 2014; 1333:18–24.
27.
WangX, JiangM, ZhouZ, et al.3D printing of polymer matrix composites: A review and prospective. Compos B Eng, 2017; 110:442–458.
28.
StansburyJW, IdacavageMJ. 3D printing with polymers: Challenges among expanding options and opportunities. Dent Mater J, 2016; 32:54–64.
29.
TofailSAM, KoumoulosEP, BandyopadhyayA, et al.Additive manufacturing: Scientific and technological challenges, market uptake and opportunities. Mater Today, 2018; 21:22–37.
30.
Piedra-CascónW, KrishnamurthyVR, AttW, et al.3D printing parameters, supporting structures, slicing, and post-processing procedures of vat-polymerization additive manufacturing technologies: A narrative review. J Dent, 2021; 109:103630.
31.
DavoudinejadA, Diaz-PerezLC, QuagliottiD, et al.Additive manufacturing with vat polymerization method for precision polymer micro components production. Procedia CIRP, 2018; 75:98–102.
32.
PagacM, HajnysJ, MaQ-P, et al.A review of Vat photopolymerization technology: Materials, applications, challenges, and future trends of 3D printing. Polymers, 2021; 13:598.
MaruoS. Stereolithography and two-photon polymerization. In: Sugioka K, ed. Handbook of Laser Micro- and Nano-Engineering. Cham: Springer International Publishing, 2020; pp. 1–25.
35.
SpangenbergA, ChiaGL, MalvalJP, et al.Preparation of molecularly imprinted polymers by two-photon stereolithography. Google Patents; 2017.
36.
PanJ, QuQ, CaoJ, et al.Molecularly imprinted polymer foams with well-defined open-cell structure derived from Pickering HIPEs and their enhanced recognition of λ-cyhalothrin. Chem Eng J, 2014; 253:138–147.
37.
SongX, WangJ, ZhuJ. Effect of porogenic solvent on selective performance of molecularly imprinted polymer for quercetin. Mater Res, 2009; 12:299–304.
Supplementary Material
Please find the following supplemental material available below.
For Open Access articles published under a Creative Commons License, all supplemental material carries the same license as the article it is associated with.
For non-Open Access articles published, all supplemental material carries a non-exclusive license, and permission requests for re-use of supplemental material or any part of supplemental material shall be sent directly to the copyright owner as specified in the copyright notice associated with the article.
