Pentafluorophenyl Research Articles

Recent trends in ultra‐fast HPLC: New generation superficially porous silica columns

New generation columns, i.e. packed with superficially porous silica particles are available as trade names with following manufacturers: Halo, Ascentis Express, Proshell 120, Kinetex, Accucore, Sunshell, and Nucleoshell. These provide ultra-fast HPLC separations for a variety of compounds with moderate sample loading capacity and low back pressure. Chemistries of these columns are C(8), C(18), RP-Amide, hydrophilic interaction liquid chromatography, penta fluorophenyl (PFP), F5, and RP-aqua. Normally, the silica gel particles are of 2.7 and 1.7 μm as total and inner solid core diameters, respectively, with 0.5-μm-thick of outer porous layer having 90 Å pore sizes and 150 m(2)/g surface area. This article describes these new generation columns with special emphasis on their textures and chemistries, separations, optimization, and comparison (inter and intra stationary phases). Besides, future perspectives have also been discussed.

Liquid chromatographic determination of microcystins in water samples following pre-column excimer fluorescence derivatization with 4-(1-pyrene)butanoic acid hydrazide

A method to measure the concentrations of microcystins (MCs) in water samples has been developed by incorporating pre-column fluorescence derivatization and liquid chromatography (LC). A solid-phase extraction for pretreatment was used to extract the MCs in water samples. The MCs were derivatized with excimer-forming 4-(1-pyrene)butanoic acid hydrazide (PBH). The MCs could then be detected by fluorescence after separation with a pentafluorophenyl (PFP)-modified superficially porous (core shell) particle LC column. The derivatization reactions of MCs with PBH proceeded easily in the presence of 4,6-dimethoxy-1,3,5-triazin-2-yl-4-methylmorpholinium (DMT-MM) as a condensation reagent, and the resulting derivatives could be easily separated on the PFP column. The derivatives were selectively detected at excimer fluorescence wavelengths (440–540nm). The instrument detection limit and the instrument quantification limit of the MCs standards were 0.4–1.2μgL−1 and 1.4–3.9μgL−1, respectively. The method was validated at 0.1 and 1.0μgL−1 levels in tap and pond water samples, and the recovery of MCs was between 67 and 101% with a relative standard deviation of 11%. The proposed method can be used to quantify trace amounts of MCs in water samples.

Simultaneous quantification of four vitamin D metabolites in human serum using high performance liquid chromatography tandem mass spectrometry for vitamin D profiling

ObjectivesFor quantification of 25-hydroxyvitamin D3 (25OH-D3), 25-hydroxyvitamin D2 (25OH-D2), 3-epi-25-hydroxyvitamin D3 (3-epi-25OH-D3) and 24R,25-dihydroxyvitamin D3 (24R,25(OH)2-D3) in human serum a high performance liquid chromatography tandem mass spectrometry (HPLC–MS/MS) method was developed and validated. Design and methodsAfter protein precipitation further purification is achieved with on-line sample preparation using a reversed phase (RP) C-4 column. Chromatographic separation is realized by a RP-column with core shell material and pentafluorophenyl (PFP) selectivity. Atmospheric pressure chemical ionization in the positive ion mode with multi‐reaction monitoring is used for analyte detection. ResultsBaseline separation of the analytes is achieved below 10min. The method is linear over the range 4.0–265.3nmol/L for 25OH-D3, 3.9–183.6nmol/L for 25OH-D2, 2.0–133.8nmol/L for 3-epi-25OH-D3 and 2.8–129.9nmol/L for 24R,25(OH)2-D3 (r2>0.998). The limit of quantification is 4.0nmol/L for 25OH-D3, 3.9nmol/L for 25OH-D2, 2.0nmol/L for 3-epi-25OH-D3 and 2.8nmol/L for 24R,25(OH)2-D3. The CVs for the intra-day and inter-day precision are <5% and <4%, respectively. Metabolite levels for a set of 50 human serum samples have been determined and resulted in the detection of considerable amounts of 3-epi-25OH-D3 and 24R,25(OH)2-D3. ConclusionsThis highly specific HPLC–MS/MS method is suitable for vitamin D profiling. There is a correlation between 25OH-D3 and 24R,25(OH)2-D3. Serum concentration of 24R,25(OH)2-D3 increases disproportionally with increasing concentration of 25OH-D3.

Preparation, nano purification, quality control and labeling optimization of [64Cu]-5,10,15,20-tetrakis (penta fluoro phenyl) porphyrin complex as a possible imaging agent

Cu-64 was produced via the 68Zn (p,αn)64Cu nuclear reaction (≈200 mCi, >95 % chemical yield at 180 μA for 1.1 h irradiation, (radionuclidic purity >96 %, copper-67 as impurity) followed by purification with amino functionalized nano magnetic oxide, Fe3O4 aiming to remove trace amount of heavy metal ions from aqueous media due to achieve ultra pure [64Cu] CuCl2 for labeling step. [64Cu] labeled 5,10,15,20-tetrakis(penta fluoro phenyl) porphyrin ([64Cu]-TFPP) was prepared using freshly prepared [64Cu] CuCl2 (Cu-64; T1/2 = 12.7 h) and 5,10,15,20-tetrakis(penta fluoro phenyl)porphyrin (H2TFPP) for 60 min at 100 °C under reflux condition (radiochemical purity: >97 % ITLC, >98 % HPLC, specific activity: 14–16 GBq/mmol). Stability of the complex was checked in final formulation and human serum for 24 h. The partition coefficient was calculated for the compound (log P = 0.73). The biodistribution of the labeled compound in vital organs of wild-type rats was studied using scarification studies and PET imaging up in 2 and 4 h after injection. A detailed comparative pharmacokinetic study performed for 64Cu cation and [64Cu]-TFPP. The complex is mostly washed out from the circulation through kidneys and liver and can be an interesting tumor imaging/targeting agent due to high specific uptake and rapid excretion through the urinary tract.

Pentafluorophenyl Ester-Functionalized Phosphorylcholine Polymers: Preparation of Linear, Two-Arm, and Grafted Polymer–Protein Conjugates

Novel pentafluorophenyl (PFP)-ester-functionalized phosphorylcholine (PC) polymers of different architectures were prepared and conjugated to lysozyme as a model protein. Linear and two-arm poly(2-methacryloyloxyethyl phosphorylcholine) (polyMPC) structures containing PFP functionality at the chain-end were prepared by atom transfer radical polymerization (ATRP) from novel initiators. Additional conjugates were prepared from phosphorylcholine-substituted cyclooctene (PC-COE) polymers containing PFP-ester bearing comonomers. The polymer-protein conjugates were characterized by HPLC, FPLC, and DLS and were seen to retain most (~80% or greater) of their native enzymatic activity. Pharmacokinetic profiles of the polymer-protein conjugates were studied in mice and found to increase the circulation half-life compared with lysozyme alone.

Effect of Ionic Liquid Additives to Mobile Phase on Separation and System Efficiency for HPLC of Selected Alkaloids on Different Stationary Phases

The silica-based stationary phases with favorable physical characteristics are the most popular in liquid chromatography. However, there are several problems with silica-based materials: severe peak tailing in the chromatography of basic compounds, non-reproducibility for the same chemistry columns, and limited pH stability. Ionic liquids (ILs) as mobile phase components can reduce peak tailing by masking residual free silanol groups. The chromatographic behavior of some alkaloids from different classes was studied on C18, phenyl, and pentafluorophenyl columns with different kinds and concentrations of ionic liquids as additives to aqueous mobile phases. Ionic liquids with different alkyl substituents on different cations or with different counterions as eluent additives were investigated. The addition of ionic liquids has great effects on the separation of alkaloids: decrease in band tailing, increase in system efficiency, and improved resolution. The retention, separation selectivity, and sequence of alkaloid elution were different when using eluents containing various ILs. The increase of IL concentration caused an increase in silanol blocking, thus conducted to decrease the interaction between alkaloid cations and free silanol groups, and caused a decrease of alkaloids retention, improvement of peak symmetry, and increase of theoretical plate number in most cases. The effect of ILs on stationary phases with different properties was also examined. The different properties of stationary phases resulted in differences in analyte retention, separation selectivity, peak shape, and system efficiency. The best shape of peaks and the highest theoretical plate number for most investigated alkaloids in mobile phases containing IL was obtained on pentafluorophenyl (PFP) phase.

Synthesis of Functional Disubstituted Polyacetylenes Bearing Highly Polar Functionalities via Activated Ester Strategy.

We demonstrate a facile synthetic route to functional disubstituted polyacetylenes bearing highly polar groups based on polymer reactions. A pentafluorophenyl (PFP) ester-containing diphenylacetylene was designed and polymerized to obtain PFP activated ester-functionalized disubstituted polyacetylene (P1). P1 was used as a parent polymer to further react separately with diverse amines, giving rise to a series of functional disubstituted polyacetylenes with a chiral moiety and hydroxyl and carboxyl groups in high yields under mild condition. Spectral characterization data indicated that the polymers' structures were well consistent with the expected results. The helicity and emission property of polymers were also studied.

Sulfonamide synthesis using N-hydroxybenzotriazole sulfonate: an alternative to pentafluorophenyl (PFP) and trichlorophenyl (TCP) esters of sulfonic acids

The N-hydroxybenzotriazole (HOBt) sulfonate esters undergo amidation under ambient conditions in the presence of di-isopropylethyl amine. This method can be applied to varieties of amines including sterically hindered amino acid esters in less time with reasonably good yields.HOBt ester of sulfonic acids can be a replacement for pentafluorophenyl and trichlorophenyl ester as well as chloride moiety of sulfonyl chloride for amidation.

Determination of perfluorinated compounds in human plasma and serum Standard Reference Materials using independent analytical methods

Perfluorinated compounds (PFCs) were measured in three National Institute of Standards and Technology (NIST) Standard Reference Materials (SRMs) (SRMs 1950 Metabolites in Human Plasma, SRM 1957 Organic Contaminants in Non-fortified Human Serum, and SRM 1958 Organic Contaminants in Fortified Human Serum) using two analytical approaches. The methods offer some independence, with two extraction types and two liquid chromatographic separation methods. The first extraction method investigated the acidification of the sample followed by solid-phase extraction (SPE) using a weak anion exchange cartridge. The second method used an acetonitrile extraction followed by SPE using a graphitized non-porous carbon cartridge. The extracts were separated using a reversed-phase C(8) stationary phase and a pentafluorophenyl (PFP) stationary phase. Measured values from both methods for the two human serum SRMs, 1957 and 1958, agreed with reference values on the Certificates of Analysis. Perfluorooctane sulfonate (PFOS) values were obtained for the first time in human plasma SRM 1950 with good reproducibility among the methods (below 5% relative standard deviation). The nominal mass interference from taurodeoxycholic acid, which has caused over estimation of the amount of PFOS in biological samples, was separated from PFOS using the PFP stationary phase. Other PFCs were also detected in SRM 1950 and are reported. SRM 1950 can be used as a control material for human biomonitoring studies and as an aid to develop new measurement methods.

A Facile Synthetic Route to Functional Poly(phenylacetylene)s with Tunable Structures and Properties

Pentafluorophenyl (PFP) ester-functionalized poly(phenylacetylene)s (PPAs, P1, P2, and P3) were designed and synthesized in desirable yields and molecular weight by using organorhodium complexes as catalysts. Furthermore, these PFP-containing PPAs were used as precursors to prepare a series of mono- and dual-functionalized PPAs by the substitution of the activated ester moieties with functional amines. The structures of the PFP-containing PPAs and the derived functional PPAs were characterized by using multiple spectroscopic techniques including GPC, FTIR, 1H NMR, 13C NMR, and 19F NMR. The experimental details and the characterization data demonstrate that activated ester synthetic route to functional PPAs is facile (just stirring the precursor polymer with proper amine(s) at room temperature for hours), efficient (complete transition from ester to amide has been confirmed), and quantitative (the relative content of a specific functionality can be precisely preset by controlling the feed ratio of the func...

The C-3 epimer of 25-hydroxyvitamin D3 is Present in Older Adults

A method based on automated on-line solid phase extraction coupled to two-dimensional liquid chromatography with tandem mass spectrometry detection (SPE-2DLC–MS/MS) is here reported for vitamin D metabolite profiling in human serum with absolute quantitation. Two-dimensional LC was configured with two complementary analytical columns, pentafluorophenyl (PFP) and C18 phases, for determination of 25 hydroxyvitamin D3 epimers and the resting bioactive metabolites of vitamin D (D3 and D2)-25-hydroxyvitamin D2, 1,25-dihydroxyvitamin D3, 1,25-dihydroxyvitamin D2 and 24,25-dihydroxyvitamin D3. Quantitative determination was supported on the use of a stable isotopic labelled internal standard for each analyte and the resulting method was validated by analysis of a standard reference material certified by the National Institute of Standards & Technology (NIST-972a) and 5 samples provided by the vitamin D External Quality Assurance Scheme (DEQAS). The limits of detection were between 9 and 90 pg/mL for the eight analytes, and precision, expressed as relative standard deviation, was lower than 11.6%. Two-dimensional LC has shown to be the key to discriminate between 25 hydroxyvitamin D3 epimers in a quantitative analysis also involving dihydroxyvitamin D metabolites.

Characterization of stationary phases by a linear solvation energy relationship utilizing supercritical fluid chromatography

Supercritical fluid chromatography was utilized in combination with the Abraham model of linear solvation energy relationship to characterize 11 different HPLC stationary phases. System constants were determined at one supercritical fluid chromatography condition for each stationary phase. The results indicate that several types of silica columns, including type B silica, type C silica, and fused core silica, are very similar in their retention behavior. Several aromatic stationary phases were characterized and it was found that, in contrast to the other phases studied, all of the aromatic stationary phases had positive contributions from the dispersion/cavity (v) term of the linear solvation energy relationship. Several aliphatic phases were characterized and there were several linear solvation energy relationship constants that differentiated the phases from each other, mainly the polar terms (dipolarity and hydrogen bonding). One stationary phase, a fused core pentafluorophenyl (PFP) phase, had very poor regression quality. The column volume of this phase was lower than the others in the study, which may have had some impact on the results of the regression.

Characterization of pertussis toxoid by two-dimensional liquid chromatography–tandem mass spectrometry

Pertussis toxoid, an acellular pertussis vaccine prepared by hydrogen peroxide treatment in the presence of Fe3+, has not been well characterized. Because the toxoid has been a part of the DTaP vaccine for infants, it is of interest and significance to have a clear understanding of its structure. The five subunits of pertussis toxin (PT) have a combined molecular weight of approximately 95,000Da. The peroxide treatment in toxoid formation introduces additional complexity into the protein sequence. To maximize sequence coverage, a two-dimensional liquid chromatography–tandem mass spectrometry (2D LC–MS/MS) approach was used to analyze the tryptic digest of toxoid as a whole. An analytical-scale high-performance liquid chromatography (HPLC) instrument using a pentafluorophenyl (PFP) column was used as the first-dimensional LC for fraction collection. The fractions were then analyzed by nanoLC–MS/MS using a C18 column to acquire collision-activated dissociation (CAD) spectra of the tryptic peptides. It is shown that a PFP column has a different peptide retention specificity from a C18 column. A combination of a PFP column and a C18 column is a viable approach for dispersing peptides in a complex mixture. From the structures of 65 peptides that represented approximately 50% of its sequence, PT was found to have sustained heavy oxidative damages during toxoid preparation. Nearly all methionine, cysteine, and (likely) tryptophan residues were oxidized. Evidence of histidine and tyrosine oxidation was also observed. In addition, a large percentage of asparagine was found hydrolyzed to aspartic acid. These findings corrrelate well with the reduction of PT toxicity by peroxide treatment.

Synthesis of Heterotelechelic α,ω Dye-Functionalized Polymer by the RAFT Process and Energy Transfer between the End Groups

The synthesis of a vinyl polymer with two different fluorescent dye end groups using reversible addition-fragmentation chain transfer (RAFT) polymerization is described. Use of a pentafluorophenyl (PFP) activated ester chain transfer agent (CTA) provided a polymer with an R end group that was reactive toward amines and a dithioester ω end group. The R PFP ester was amidated with Oregon Green Cadaverin. This did not harm the ω dithioester, which was subsequently aminolyzed with an excess of n-propylamine in the presence of Texas Red-2-sulfonamidoethyl methanethiosulfonate, resulting in a disulfide bond connecting the second dye to the polymer chain. Excess dyes and side products were removed by thin layer chromatography (TLC). Gel permeation chromatography (GPC) using a UV-vis detector could verify the presence of each dye on the polymer chain and the absence of free dyes. The synthesis of the polymer by a living radical technique and the mild complementary conjugation methods conducted after polymerization at each end group allowed to introduce complex dye residues possessing high brightness and photostability. In particular, fluorescent dyes capable of acting as donor and acceptor for electronic excitation energy transfer were chosen. Time-resolved fluorescence measurements were used to determine the time constant of energy transfer between the end groups of isolated polymer chains. Assuming a Forster-type process, an average end- € to-end distance of 4.5 nm was calculated, which was in reasonable agreement with data obtained from light scattering.

Synthesis of Hetero-Telechelic α,ω Bio-Functionalized Polymers

Reversible addition-fragmentation chain transfer (RAFT) polymerization was used to synthesize poly[diethylene glycol monomethylether methacrylate] (PDEGMA) (M(n) = 6250 g/mol, PDI = 1.14) with a pentafluorophenyl (PFP) activated ester and a dithioester end group. The hormone thyroxin (T4) was quantitatively attached to the PFP activated ester alpha end group via its amino group. The omega-terminal dithioester was not harmed by this reaction and was subsequently aminolyzed in the presence of N-biotinylaminoethyl methanethiosulfonate, yielding a polymer with a thyroxin and a biotin end group with very high heterotelechelic functionality. The polymer was characterized by (1)H, (13)C, and (19)F NMR, UV-vis, and IR spectroscopy and gel permeation chromatography. The thyroxin transport protein prealbumin with two thyroxin binding sites and streptavidin, which has four biotin binding sites, was conjugated using the biotarget labeled polymer, resulting in the formation of a protein-polymer network, confirming the heterotelechelic nature of the polymer. Polymer-protein microgel formation was observed with dynamic light scattering. To realize a directed protein assembly, prealbumin was immobilized onto a surface, exposing one of its two thyroxin binding groups and thus allowing the conjugation with the thyroxin alpha end group of the heterotelechelic polymer. The biotin omega end group of the attached polymer layer enabled the subsequent immobilization of streptavidin, yielding a defined multilayer system of two proteins connected with the synthetic polymer (efficiency of streptavidin immobilization 81% based on prealbumin). Without the polymer, no streptavidin immobilization occurred. The layer depositions were monitored by surface plasmon resonance. The synthetic approach of combining PFP activated esters with functional MTS reagents presents a powerful method for obtaining well-defined heterotelechelic (bio-) functionalized polymers.

Thermo- and Light-Responsive Polymers Containing Photoswitchable Azobenzene End Groups

Telechelic thermo- and light-responsive polymers based on poly(oligo(ethylene glycol) methyl ether methacrylate) P(OEGMA) with azobenzene functionalities at the end groups were synthesized. In a reversible addition−fragmentation chain transfer (RAFT) polymerization using a functionalized chain transfer agent (CTA) containing a pentafluorophenyl (PFP) activated ester, oligo(ethylene glycol) methyl ether methacrylate (OEGMA, Mn ∼ 300 g mol−1) could successfully be polymerized with good control over molecular weight, very high conversions, and narrow molecular weight distributions. Polymers derived from this CTA possessed an activated ester at the α-end of the polymer chain as well as a dithioester ω-terminus. The ω-dithioester group of each polymer chain could quantitatively be either removed with AIBN treatment or substituted with a PFP ester by using a modified diazo compound. As a consequence, a postmodifiaction of the telechelic reactive end groups was possible through a polymer analogous reaction with amino-functionalized azobenzene. P(OEGMA) polymers containing azobenzene end groups showed a reversible light- and temperature-controlled phase transition in water. Higher values for the lower critical solution temperature (LCST) were measured after irradiation of the aqueous polymer solutions due to the higher polarity of cis-azobenzene. The LCST differences between irradiated and nonirradiated solutions increased linearly upon the ratio of azobenzene units up to 4.3 °C.

Simultaneous Determination of Medicinal Ingredients in So-called Health-promoting Food Using Liquid Chromatography Tandem Mass Spectrometry with a Pentafluorophenyl Stationary Phase

An analytical method using liquid chromatography tandem mass spectrometry equipped with electrospray ionization (ESI) was demonstrated for the determination of medicinal ingredients, such as fenfluramine (FF), Nnitrosofenfluramine (NFF), sibutramine (SIB), sildenafil (SDF), vardenafil (VDF), tadalafil (TDF) and xanthoanthrafil (XAF), in so-called health-promoting food. These analytes were clearly separated with acetonitrile-water (40 : 60) containing 4 mM formic acid and 8 mM ammonium formate used in the mobile phase on a pentafluorophenyl (PFP) column under isocratic conditions. The retention times of FF, SIB, SDF and VDF on the PFP column were longer than those on the C18 column under the same mobile phase conditions. Within wide ranges, all peaks were proportional and the coefficient of determination (r 2 ) showed more than 0.9950 in a linear regression analysis. The limit of quantification (LOQ) of the developed method was 0.8–42.2µg/l (S/N = 10). The recoveries of analytes admixed with commercially available health-promoting food ranged from 80.2 to 113.3% and were acceptable for quantitative analysis. Analytes of more than 2µg in a health-promoting food sample (0.5 g) were able to be identified by the European Communities (EC) criteria.

Synthesis of Reactive Telechelic Polymers Based on Pentafluorophenyl Esters

A diazo initiator and a chain transfer agent (CTA), both containing a pentafluorophenyl (PFP) activated ester, were synthesized. In a RAFT polymerization using the functionalized chain transfer agent (PFP-CTA), methyl methacrylate (MMA), diethylene glycol monomethyl ether methacrylate (DEGMA), poly(ethylene glycol) monomethyl ether methacrylate (PEGMA), and lauryl methacrylate (LMA) could successfully be polymerized into homopolymers and diblock copolymers with good control over molecular weight, very high conversions, and narrow molecular weight distributions. Polymers derived from the PFP−CTA possessed an activated ester at the α-end of the polymer chain, which could be reacted with amines with high conversions. The terminal ω-dithioester group of each polymer chain could quantitatively be removed by treating the polymer with an excess of AIBN, leaving the α-PFP ester functionality intact. Accordingly, the pentafluorophenyl ester diazo compound could successfully be employed to functionalize RAFT polymers with a PFP ester at their ω-end. As a consequence, functionalization of both end groups was possible and led to telechelic polymers, exhibiting an active ester at both ends of the polymer chain. As an example, a high molecular weight PMMA was prepared by polycondensation with ethylenediamine.

Simultaneous determination of main taxoids in Taxus needles extracts by solid‐phase extraction‐high‐performance liquid chromatography with pentafluorophenyl column

A simple and accurate RP-HPLC method with pentafluorophenyl (PFP) column was developed for the simultaneous determination of six taxoids, i.e. paclitaxel, 10-deacetylbaccatin III (10-DAB III), 7-xylosyl-10-deacetyltaxol (7-xyl-10-DAT), 10-deacetyltaxol (10-DAT), cephalomannine and 7-epi-10-deacetyltaxol (7-epi-10-DAT), in the extracts from the needles of three Taxus species. The mobile phase consisted of acetonitrile (A) and water (B), and the extracts were separated using gradient elution program: 30% A at the first 7 min, and then ramped to 42% A at 8 min, held until 38 min. The developed method was validated with satisfactory precision (RSD < 2.61%), repeatability (RSD < 2.92%) and recovery (95.19-104.47%). The above taxoids in the extracts of Taxus cuspidata, T. chinensis and T. media were analyzed with the developed RP-HPLC method, and the results showed that the contents of different taxoids in three mentioned species were distinct. Maximal amounts of 10-DAB III, 7-xyl-10-DAT and 7-epi-10-DAT appeared in T. chinensis, while T. media possessed the highest content of 10-DAT, cephalomannine and paclitaxel. The developed method is accurate and efficient. It can be reliably used in the improved determination of taxoids for the quality control of Taxus species.

Effect of tris(methoxy diethylene glycol) borate on ionic conductivity and electrochemical stability of ethylene carbonate-based electrolyte

The effect of tris(methoxy diethylene glycol) borate (TMDGB) on the coordination structure between ethylene carbonate (EC) solvents with high permittivity and ClO4− anions has been investigated by using a Fourier transform infrared (FT-IR) spectroscopy. The results of FT-IR analyses manifested that the boron atom of TMDGB anion receptor forms the complex with ClO4− anions. Even though Lewis acid–base interaction between the TMDGB anion receptor and ClO4− anions in the electrolyte solution lead to the prominent enhancement of both the dissociation degree of lithium salts and the lithium ion transference number, the ionic conductivity of the EC-based electrolyte solution decreased due to the trap of ClO4− anions by introducing the TMDGB anion receptor. The electrochemical stability of gel polymer electrolyte based on semi-interpenetrating network (IPN) structure with tris(pentafluoro phenyl) borane (TPFPB) or TMDGB anion receptor was obviously improved.