Post-Polymerization Modifications of Polymeric Monolithic Columns: A Review
Abstract
:1. Introduction
2. Photo-Grafting Reactions
2.1. Monolithic Columns Grafted with Ionizable Exchange Groups
2.2. Grafted Monolithic Columns for Biomolecule Immobilization
2.3. Monolithic Columns with Bonded Ligands
Monolith | Reaction | Graft energy | Time | Reference |
---|---|---|---|---|
Poly(BuMA-co-EDMA) | Single and sequential two step grafting of monomers. | 500 W | 60 * min | [7] |
Poly(BuMA-co-EDMA) | Sequential grafting of PEGMA and VAL. | 500 W | 60 * min | [8] |
Poly(BuMA-co-EDMA) | Single step grafting of gradients of AMPS. | 500 W | 1 to 10 min | [10] |
Poly(BuMA-co-EDMA) | Single step grafting of gradients of AMPS. | 3 J/cm2 | N/A | [11] |
Poly(BuMA-co-EDMA) | Sequential grafting of PEGMA, VAL, and SPM. | 1 J/cm2 each step | N/A | [13] |
Poly(BuMA-co-EDMA) | Single step grafting of AMPS. | 0.25 to 7 J/cm2 | N/A | [29] |
Poly(BuMA-co-EDMA) | Single step grafting of AMPS and butyl acrylate. | 500 W | 0.5 to 1.5 min | [36] |
Poly(BuMA-co-EDMA) | Single step grafting of AMPS and VAL. | 500 W | 30 min | [37] |
Poly(BuMA-co-EDMA) | Single step grafting of META and butyl acrylate. | 1.4 mW/cm2 | 3 min | [67] |
Poly(BuMA-co-EDMA) | Single step grafting of VAL for dual function monolith. | 15 mW/cm2 | 3 min | [68] |
Poly(GMA-co-EDMA) | Single step grafting of META. | 0.25 J/cm2 | N/A | [69] |
Poly(BuMA-co-EDMA) | Single step grafting of AMPS and VAL. | N/A | 60, 30 min respectively | [70] |
Poly(GMA-co-EDMA) | Sequential grafting of PEGMA and VAL. | 12 mW/cm2 | 4 * 1 to 6 min (VAL) | [71] |
Poly(BuMA-co-EDMA) and Poly(GMA-co-EDMA) | Sequential grafting of PEGMA and VAL. | N/A | 4 *, 2 min | [72] |
Poly(BuMA-co-EDMA) | Sequential grafting of PEGMA and VAL. | 3 * J/cm2 | N/A | [74] |
Poly(BuMA-co-EDMA) | Single step grafting of VAL. | 3 J/cm2 | N/A | [75] |
Poly(BuMA-co-EDMA) | Single step grafting of spiropyran monomer using VIS LED at 660 nm. | 0.5 cd | 2 min | [77] |
Poly(LMA-co-EDMA) | Multi step grafting of VAL. | 1 * J/cm2 | N/A | [78] |
Poly(LMA-co-EDMA) | Multi step grafting of GMA. | 1 * J/cm2 | N/A | [79] |
2.4. Monolithic Columns Grafted with Heterogeneous Grafting Energies
3. “Click” Chemistry
Monolith | Reaction | λ (nm) | Temperature (C°) | Time | Reference |
---|---|---|---|---|---|
Poly(NAS-co-EDMA) | Propargylamine modification to produce surface alkyne. Click grafting of 1-adamantanethiol using UV irradiation at 313 nm, using darocure as initiator. | 313 | N/A | 30, 60, 120, and 180 min | [43] |
Poly(GMA-co-EDMA), Poly(GMA-co-MMA-co-EDMA), Poly(GMA-co-HEMA-co-EDMA) | Surface sulfhydryl groups clicked with (S)-N-(4-allyloxy-3,5-dichlorobenzoyl)-2-amino-3,3-dimethylbutanephosphonic acid in the presence of AIBN initiator. | N/A | 60 | 24 h | [50] |
Poly(GMA-co-EDMA) | Surface thiol groups clicked with O-9-tert-butylcarbamoylquinine in the presence of AIBN. | N/A | 60 | 24 h | [87] |
Poly(IEM-co-MMA-co-EGDMA) | Monoliths modified with 1-octanol, 1-decanol, 1-dodecanol, 1-octadecanol, n-decylamine and 1-decanethiol. | N/A | 60 | N/A | [88] |
Poly(GMA-co-EDMA) | Monolith thiolated with cysteamine, with cleavage of the disulphide thus exposing thiols. MEDSA or LMA clicked using either heat or UV initiation. | 360 | 80 | N/A | [89] |
Poly(NAS-co-EDMA) | Allylamine modified monolith surface reacted with 1-octadecanethiol in the presence of AIBN and UV initiation. | 365 | N/A | 4 h | [90] |
Poly(propargyl methacrylate-co-EDMA) | Click addition of 1-azidooctane and 1-azidooctadecane using a Cu(I) catalyst. | N/A | 30 | 120 h | [91] |
Poly(GMA-co-EDMA) and poly(VBC-co-DVB) | Azide modified surfaces clicked with 1-decyne using a Cu(I) catalyst. | N/A | 30 to 60 | 48 h | [92] |
Poly(3-(Trimethoxysilyl)propyl acrylate-co-propargylacrylate-co-AMPS-co-TRIM-co-PETRA) | Active surface modified with cinnamidyl azide or 6-azido-6-deoxy-beta-cyclodextrin. | N/A | 84 | 16 h | [93] |
3.1. Thiol-Ene Click Reactions in Monolithic Column Functionalization
3.2. Thiol-Yne Click Reactions in Monolithic Column Functionalization
4. Thermally Initiated Graft Chain Growth
5. Hypercross-Linking
Monolith | Reaction | Temperature (°C) | Time (h) | Reference |
---|---|---|---|---|
Poly(styrene-co-VBC-co-DVB) | Solution of FeCl3 in DCE flushed across column (held in ice for 2 h). | 80 | 24 | [112] |
Poly(styrene-co-VBC-co-DVB) | Solution of FeCl3 in DCE flushed across column (held in ice for 1 h). | 80 | 24 | [114] |
Poly(styrene-co-VBC-co-DVB) and poly(4-methyl styrene -co-VBC-co-DVB) | Solution of FeCl3 in DCE flushed across column (held in ice for 2 h). | 90 | 2 | [115] |
Poly(styrene-co-VBC-co-DVB) | Solution of FeCl3 in DCE flushed across column. | 90 | 2 | [116] |
Poly(styrene-co-VBC-co-DVB) | Solution of FeCl3 in DCE flushed across column. Thermal grafting of MEDSA using 4,4’-azobis(4-cyanovaleric acid) (8 h at 70 °C). | 90 | 2 | [117] |
Poly(4-methyl styrene -co-VBC-co-DVB) | Hypercross-linked monolith brominated to support cysteamine modification (microwave assisted, 30 min). Disulphide bonds cleaved. Pendent thiols modified with AuNPs. | 90 | 4 | [118] |
6. Nano-Particles and Nano-Structures
Monolith | Reaction | Temperature (C°) | Time | Nano-Particle Type | Reference |
---|---|---|---|---|---|
Poly(BuMA-co-EDMA) and poly(LMA-co-EDMA) | Introduction of photo-grafted zones of monomers suitable for amination, supporting AuNP immobilization. Dual function monolith. | Room Temperature (RT) | N/A | 20 nm Au | [9] |
Poly(GMA-co-EDMA) and poly(styrene-co-DVB) | For poly(STY-co-DVB) chlorosulfonic acid in dry dichloromethane was used for sulfonation. For poly(GMA-co-EDMA), sulfonation was performed in three techniques: (i) 4-hydroxybenezenesulfonic acid and triethylamine, (ii) thiobenzoic acid and triethylamine (thiol groups were oxidized by pumping a solution of tert-butylhydroperoxide). (iii) Sodium sulfite and tetra-n-butylammonium hydroxide. | 60, 60, 70, respectively | 20 h each | 65 nm Latex | [28] |
Poly(BuMA-co-AMPS-co-EDMA) | Co-polymerization of sulfonic acid group suitable for latex nano-particle agglomeration. | RT | 2 h | 60 nm Latex | [46] |
Poly(BuMA-co-AMPS-co-EDMA) | Co-polymerization of sulfonic acid group suitable for latex nano-particle agglomeration. | RT | 2 h | 65 nm Latex | [47] |
Poly(BuMA-co-AMPS-co-EDMA) | Co-polymerization of sulfonic acid group suitable for latex nano-particle agglomeration. | RT | 2 h | 65 nm Latex | [48] |
Poly(GMA-co-EDMA) | Introduction of surface immobilized AuNPs via cysteamine and subsequent cleavage of the disulfide bond, to reveal surface thiols. AuNP modification. | RT | N/A | 10 nm Au | [118] |
Poly(GMA-co-EDMA) | Generation of quaternary ammonium for IONP immobilization. | RT | N/A | 19 nm iron oxide | [119] |
Poly(EDMA) | Preparation of AuNP modified extraction pipette tip, for glycoprotein selectivity. | RT | N/A | 20 nm Au | [129] |
Poly(GMA-co-EDMA) | Coupling of α-glucosidase to AuNP modified monolith for PMME. | RT | 3 h | 15 nm Au | [130] |
Poly(GMA-co-EDMA) | For AuNP immobilization, and functionalizing groups such as 3-mercapto propionic acid (CEC), 1-octadecanethiol (RPLC), and sodium 2-mercaptoethane sulfonate (SCX). | RT | N/A | 15 nm Au | [131] |
Poly(NAS-co-EDMA) | Surface generation of alkyne group, followed by thiol-yne photo-addition of cysteamine for AuNP modification. | RT | N/A | 20 nm Au | [132] |
Poly(GMA-co-EDMA) | Introduction of surface AuNPs by generation of surface thiols from surface epoxide groups. Two methods were used: (i) Hydrogen sulfide, and (ii) Cysteamine. | 100RTRT | 30 min2 h20 min | 40–50 nm Au | [133] |
Poly(BuMA-co-EDMA) | Preparation of thiolated and aminated surfaces and comparison of immobilization pathways for AuNPs. | RT | N/A | 20 nm Au | [134] |
Poly(GMA-co-EDMA) | Immobilization of SNPs upon a polymer monolith. | RT | 60 min | 50 nm Ag | [127] |
Poly(HEMA-co-EDMA) | Generation of polymer monolith extraction device within a pipette tip, immobilized with IONPs via surface grafted functional groups (META). | RT | N/A | 20 nm iron oxide | [135] |
Poly(NIPAAm-co-GMA-co-EDMA) | Generation of γ-alumina nano-particle monolith for PMME. | 60 | 14 h | 10–20 nm Al2O3 | [136] |
Poly(GMA-co-EDMA), poly(BuMA-co-EDMA), poly(GMA-co-BuMA-co-EDMA) | Immobilization of Pd/Pt NFs via aminated surface groups. | RT | 72 h | Pd/Pt NFs | [137] |
Poly(GMA-co-EDMA) | Coating of monolith surface with graphene and graphene oxide nano-sheets for PMME. | RT | N/A | Graphene nano-sheets | [138] |
Poly(GMA-co-EDMA) | Encapsulation of MWCNTs and surface attachment of MWCNTs via surface aminated groups. | RT | N/A | MWCNTs | [139] |
6.1. Polymeric Nano-Particles
6.2. Gold Nano-Particles
6.3. Other Metallic Nano-Particles
6.4. Carbon Nano-Structures
7. Concluding Remarks
List of Abbreviations:
AMPS | 2-acrylamido-2-methyl-1-propanesulphonic acid |
AIBN | α, α’-azoisobutyronitrile |
ATP | adenosine triphosphate |
ATRP | atom transfer radical polymerization |
BPO | benzoyl peroxide |
BSA | bovine serum albumin |
BuMA | butyl methacrylate |
CEC | capillary electrochromatography |
CE | capillary electrophoresis |
COC | cyclic olefin copolymer |
DAP | 2,2-dimethoxy-2-phenylacetophenone |
DCE | dichlorethane |
DMF | dimethyl formamide |
DVB | divinyl benzene |
EDMA | ethyleneglycol dimethacrylate |
EOF | electroosmostic flow |
GFP | green fluorescent protein |
GMA | glycidyl methacrylate |
AuNP(s) | gold nano-particle(s) |
HEMA | hydroxyethyl methacrylate |
HILIC | hydrophilic interaction liquid chromatography |
IDA | iminodiacetic acid |
IEM | isocyanoethyl methacrylate |
IONP(s) | iron oxide nano-particle(s) |
LMA | lauryl methacrylate |
MEDSA | N,N-dimethyl-N-methacryloxyethyl-N-(3-sulfopropyl) ammonium betaine |
META | methacryloyloxyethyl trimethylammonium chloride |
MMA | methyl methacrylate |
MST | 4-methyl styrene |
MWCNT(s) | multi-walled carbon nano-tube(s) |
NAS | N-acryloxysuccinimide |
NF(s) | nano-flower(s) |
OEG | oligoethylene glycol |
PEGMA | polyethyleneglycol methacrylate |
PEI | polyethylimine |
PMME | polymer monolith micro-extraction |
PTFE | Teflon |
RAFT | reversible addition-fragmentation chain transfer |
RP | reversed-phase |
ROMP | ring opening metathesis polymerization |
sC4D | scanning capacitively coupled contactless conductivity detection |
SEM | scanning electron microscope |
SNP(s) | silver nano-particle(s) |
SPE | solid phase extraction |
SPM | sulphopropyl methacrylate |
STY | styrene |
TEMPO | 2,2,6,6-tetramethylpiperidyl-1-oxy |
TRIM | trimethylolpropane trimethacrylate |
VAL | vinyl azlactone |
VBC | vinylbenzyl chloride |
Acknowledgments
Conflicts of Interest
References
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Currivan, S.; Jandera, P. Post-Polymerization Modifications of Polymeric Monolithic Columns: A Review. Chromatography 2014, 1, 24-53. https://doi.org/10.3390/chromatography1010024
Currivan S, Jandera P. Post-Polymerization Modifications of Polymeric Monolithic Columns: A Review. Chromatography. 2014; 1(1):24-53. https://doi.org/10.3390/chromatography1010024
Chicago/Turabian StyleCurrivan, Sinéad, and Pavel Jandera. 2014. "Post-Polymerization Modifications of Polymeric Monolithic Columns: A Review" Chromatography 1, no. 1: 24-53. https://doi.org/10.3390/chromatography1010024