1188423-16-6

Basic information

• Product Name: Dimethoxypillar[5]arene
• Synonyms: Dimethoxypillar[5]arene;Dimethyoxypillar[5]arene
• CAS NO: 1188423-16-6
• Molecular Formula: C45H50O10
• Molecular Weight: 750.8725
• EINECS: -0
• Mol File: 1188423-16-6.mol
• Article Data: 69

Chemical Properties

• Melting Point: 249°C(lit.)
• Boiling Point: 905.8±65.0 °C(Predicted)
• Appearance: /
• Density: 1.146±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Dimethoxypillar[5]arene(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethoxypillar[5]arene(1188423-16-6)
• EPA Substance Registry System: Dimethoxypillar[5]arene(1188423-16-6)

Safety Data

• Hazardous Substances Data: 1188423-16-6(Hazardous Substances Data)

Usage

Uses

Dimethoxypillar[5]arene (CAS# 1188423-16-6) is a pillararene derivative. When crosslinked to produce a 3D polymer network, dimethoxypillar[5]arene is used in the removal of organic micropollutants from water. Dimethoxypillar[5]arene is an excellent building block for further funtionalized pillarine derivatives.

Upstream product

• 100964-58-7 2,5-bis(ethoxymethyl)-1,4-dimethoxybenzene 
• 150-78-7 1,4-dimethoxybezene 
• 75-09-2 dichloromethane 
• 50-00-0 formaldehyd 
• 5471-84-1 1,4-bis(2-bromoethoxy)benzene 
• 111647-69-9 1,4-bis(4-methoxyphenoxy)butane 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 60732-17-4 2,5-dimethoxybenzyl bromide 
• 33524-31-1 2,5-dimethoxybenzyl alcohol 
• 20744-11-0 6-(4-methoxyphenoxy)hexyl bromide 

Relevant articles and documents

Photolysis of the BODIPY dye activated by pillar[5]arene

Here, a pseudo[3]rotaxane comprising a fluorescent BODIPY derivative and pillar[5]arene was conveniently fabricatedviahost-guest complexation. Importantly, in this system, the efficient photodecomposition of the BODIPY derivative in the presence of pillar

Fulleropillar[4]arene: The Synthesis and Complexation Properties

A multihydroquinone ether dialdehyde derivative 2 was incidentally obtained through an unexpected ring opening of pillar[4]arene[1]quinone 1. And the Prato reaction of 2 with [60]fullerene led to [60]fullerene bisadducts, from which trans-4 cyclic regioisomer 3 was isolated and characterized. The fulleropillar[4]arene 3 showed a larger cavity and can accommodate a viologen derivative C12V2+with a much stronger affinity than permethyl pillar[5]arene (MP5) and pillar[4]arene[1]quinone 1.

A low pH sensor from an esterified pillar[5]arene

An esterified pillar[5]arene has been incorporated into a PVC electrochemical membrane. The resulting pH-responsive sensor functions in the range of pH 1 to 4 in a non-linear manner. The Royal Society of Chemistry.

Orthogonal Self-Assembly of a Two-Step Fluorescence-Resonance Energy Transfer System with Improved Photosensitization Efficiency and Photooxidation Activity

During the past few decades, fabrication of multistep fluorescence-resonance energy transfer (FRET) systems has become one of the most attractive topics within supramolecular chemistry, chemical biology, and materials science. However, it is challenging t

Inclusion complexes of selected amines with pillar[5]arenes: experimental and molecular dynamics study

Selected amines were allowed to form inclusion complexes with selected synthesized pillar[5]arenes. Formation of inclusion complexes were confirmed by MALDI–TOF, ESI–MS analyses and 1H NMR spectroscopy. The complexation was supported by molecul

Syntheses of copillar[5]arenes by Co-oligomerization of different monomers

(Equation Presented). Three copillar[5]arenes, pillar[5]arenes containing different repeating units, were successfully prepared by co-oligomerization of different monomers. It was demonstrated that the yields of pillararenes could be improved by using hydroquinone diethers with appropriate aliphatic chain lengths. Pseudorotaxane-type threaded structures were obtained in the solid state by the inclusion of an n-hexane molecule into the cavity of either a homopillar[5]arene, a pillar[5]arene containing only one repeating unit, or a copillar[5]arene.

One-pot synthesis of pillar[n]arenes catalyzed by a minimum amount of TfOH and a solution-phase mechanistic study

A practical and effective trifluoromethanesulfonic acid (TfOH)-catalyzed cyclooligomerization strategy was developed for the synthesis of functionalized pillar[n]arenes and copillar[5]arenes from 1,4-dialkoxybenzenes with paraformaldehyde under mild reaction conditions, and the reaction mechanism of solution-phase catalytic synthesis of pillararenes was investigated by room-temperature X-band ESR spectroscopy, mass spectroscopy, NMR and control experiments, suggesting a free radical process initially and a Friedel-Crafts alkylation process during the consequent coupling and ring-closure stage.

A pillar[5]arene-based 3D network polymer for rapid removal of organic micropollutants from water

Organic micropollutants are posing great challenges to global water resources, especially for non-biodegradable synthetic chemicals. In this study, a carboxyl-derived pillar[5]arene (P5) and p-phenylenediamine (PPD) were crosslinked to produce a 3D network polymer, P5-P, for the adsorption and removal of organic micropollutants from water. This 3D network polymer sequesters a variety of organic micropollutants in water with rapid adsorption rates and large uptake amounts, much greater than those of conventional activated carbon. Especially, this polymer demonstrates superior adsorption performance for fluorescein sodium and methyl orange and it can be fully regenerated multiple times by a mild washing procedure. The structure of this 3D network polymer and its adsorption mechanisms have been confirmed by solid-state nuclear magnetic resonance (SSNMR). The excellent pollutant removal ability demonstrates the promise of the pillar[5]arene-based 3D network polymer for rapid waste-water treatment.

A supramolecular nanoprodrug based on a boronate ester linked curcumin complexing with water-soluble pillar[5]arene for synergistic chemotherapies

A supramolecular nanoprodrug based on the host-guest complexation of water-soluble pillar[5]arene (WP5) and a boronate ester linked curcumin (Cur) was constructed, which had dual-responsiveness towards pH and GSH, allowing the drug to be selectively released in hepatoma cells. In vitro studies revealed that the Dox-loaded WP5G-Cur nanoprodrug achieved co-delivery of Dox/Cur. The anti-cancer efficiency could be enhanced through synergistic chemotherapies of Dox/Cur.

Cascade catalytic nanoplatform constructed by laterally-functionalized pillar[5]arenes for antibacterial chemodynamic therapy

Chemodynamic therapy (CDT) is an emerging approach to overcome bacterial infections that can efficiently convert hydrogen peroxide (H2O2) to generate highly toxic hydroxyl radicals (˙OH). How to develop safe and effective CDT-based strategies is in high demand but challenging. Herein, a cascade catalytic nanoplatform (GOx-NCs/Fe3O4) was designed by absorbing glucose oxidase (GOx) onto the surface of covalent-assembled polymer capsules (NCs) encapsulating Fe3O4nanoparticles. With the presence of glucose, GOx could effectively catalyze it to produce H2O2and result in a decrease in pH value, both of which would assist the subsequent Fenton reaction. Encapsulated Fe3O4nanoparticles would subsequently trigger H2O2to produce ˙OH, which could make antibacterial CDT come true. More importantly, the polymer capsules exhibited little to no cytotoxicity towards mammalian cells, which might provide more opportunities and potential to apply in other fields.

Hybrid [ n ]arenes through thermodynamically driven macrocyclization reactions

Hybrid [n]arenes, the class of medium-sized macrocyclic compounds consisting of different alkoxybenzene units, were obtained by a simple, one-pot, direct condensation of two different alkoxybenzenes with formaldehyde catalyzed by a Br?nsted acid (trifluoroacetic acid). We have shown that, under Br?nsted acid catalysis, this reaction is reversible and therefore governed by the relative stability of the products. The main macrocyclic products are hybrid [n]arenes consisting of four alkoxybenzene units of [2 + 2] or [3 + 1] stoichiometry. However, an unusual [3 + 2] hybrid macrocycle was also obtained as a main product of the condensation between 1,4-dimethoxybenzene, 1,3,5-trimethoxybenzene, and formaldehyde. The stability of the hybrid products and the reversibility of the reaction were further confirmed by a scrambling experiment, involving pillar[5]arene and per-O-methylated resorcin[4]arene. The scrambling experiment has given hybrid macrocycles in yields comparable with those obtained in condensation reactions. NMR spectra and X-ray structures of hybrid [n]arenes indicate that 1,2- and 1,3-dialkoxybenzene units are flexible parts of macrocyclic rings. However, the 1,4-dialkoxybenzene units present considerable steric hindrance, resulting in the formation of isomers and inherently chiral macrocycles due to inhibited rotation. The recognition properties toward various organic cations were also determined. Highly selective recognition of the N-methylpyridinium cation was observed for the [3 + 2] hybrid macrocycle.

Facile, rapid, and high-yield synthesis of pillar[5]arene from commercially available reagents and its X-ray crystal structure

We monitored the progress of formation of dimethoxypillar[5]arene by size-exclusion chromatography. Surprisingly, the cyclization reaction completely finished in just 3 min. By improving the reaction conditions and purification process, we successfully obtained dimethoxypillar[5]arene in a short time and in high yield (71%) from commercially available reagents. By improving the deprotection reaction of the methoxy moieties, pillar[5]arene was isolated quantitatively. Single crystal X-ray analysis confirmed the structure of pillar[5]arene in the solid state.

Pillarquinone-Based Porous Polymer for a Highly-Efficient Heterogeneous Organometallic Catalysis

Pillar[5]quinone (PQ[5])-based porous polymer has been prepared by crosslinking and oxidating pillar[5]arene (PA[5]). Quinone was used as an unorthodox ligand to load palladium-catalyst with high loading ratio (up to 12.0 wt %). Catalyst was well dispersed on solid support in the form of Pd2+-specie. Pd-loaded PQ[5]-based heterogeneous catalyst was highly efficient for Suzuki-coupling reactions (22- to 1485-fold higher than Pd/C based on turnover frequency). It was superior compared to other existing heterogeneous catalysts for selective catalytic reaction. This heterogeneous catalyst had good thermo-stability, and could be reused and recycled.

A hybrid porous material from a pillar[5]arene and a poly(ionic liquid): Selective adsorption of n-alkylene diols

A macro-/mesoporous polymeric network with densely incorporated pillar[5]arene functionality was prepared via ionic complexation between a polymerized ionic liquid and carboxylated pillar[5]arene. It retained the solution-state host-guest property of the pillar[5]arene and was successfully applied as a selective absorbent for n-alklyene diols. The Royal Society of Chemistry 2014.

Restricting shuttling in bis(imidazolium)…pillar[5]arene rotaxanes using metal coordination

Metal coordination to a series of bis (imidazolium)…pillar[5]arene [2]rotaxanes through the formation of metal-carbene bonds facilitates a new strategy to restrict the shuttling motion in [2]rotaxanes. Whereas the pillar[5]arene macrocycle rapidly shuttle

Potential 129Xe-NMR biosensors based on secondary and tertiary complexes of a water-soluble pillar[5]arene derivative

We report on the first secondary and tertiary complexes of the pillar[5]arene derivative 3 with xenon in water. We show that the chemical shift of the encapsulated xenon provides information on the type of the formed complex suggesting that 3 has the potential to be used as a platform for NMR biosensors.

Pillar[n]arene-based porous polymers for rapid pollutant removal from water

Pillar[n]arene (PA[n], n = 5 or 6) based porous polymers (P-PAP[n]s) were prepared by crosslinking PA[n]s and used as adsorbents to remove pollutants from water via host-guest interactions. These new materials are adsorbents for a wide range of contaminants with fast removal kinetics. The adsorption is especially efficient for herbicide paraquat with very fast uptake kinetics (k2 = 33.3 g mg?1 min?1, at least 5 times faster than that of any existing adsorbent for paraquat) and a high removal capacity (209 mg g?1).

A dimethoxypillar[5]arene/azastilbene host-guest recognition motif and its applications in the fabrication of polypseudorotaxanes

Pillar[n]arenes, known as the fifth generation of host macrocycles since 2008, have become a popular topic over the past ten years. Until now, the studies of pillar[n]arenes were mainly focused on pillar[5]arenes owing to their easy synthesis and high yields. In particular, 1,4-dimethoxypillar[5]arene (DMP5), which shows a simple structure, efficient synthesis and high yield, has played important roles in the construction of various advanced supramolecular architectures. However, DMP5 has only displayed host-guest binding properties towards some guests. Therefore, the investigation of the host-guest chemistry of DMP5 should be able to greatly promote the development of pillararene chemistry. Herein, a photosensitive azastilbene derivative was chosen as a neutral guest to study the host-guest binding and stimuli-responsive behavior with DMP5. In addition, the binding behavior of DMP5 towards a series of analogous neutral guest molecules was investigated to study the driving forces of the host-guest interaction between DMP5 and the azastilbene guest. Moreover, the [2]pseudorotaxane based on DMP5 and the azastilbene guest was used to construct a polypseudorotaxane via metal coordination.

A facile, moisture-insensitive method for synthesis of pillar[5]arenes - The solvent templation by halogen bonds

A new, very efficient, and selective preparation method of peralkylated pillar[5]arenes is presented. By replacing typical Lewis acids with trifluoroacetic acid (TFA) we were able to eliminate the need of anhydrous conditions without a loss of effectiveness. The method is highly practical: a) it is moisture-insensitive, b) starting from simple and cheap reagents and reactants, and c) allows for chromatography-free isolation of the products. The results indicate that the interactions with solvent molecules can modulate stability of the products and influence the reaction outcome. Dichloromethane (DCM) and dichloroethane (DCE) are complexed within the cyclopentamer cavity with association constants of 120 M-1 and 600 M-1, respectively (CDCl3). The interactions involve a combination of hydrogen-pi and halogen-pi bonds.

Pillar[n]MaxQ: A New High Affinity Host Family for Sequestration in Water

We report the synthesis, X-ray crystal structure, and molecular recognition properties of pillar[n]arene derivative P[6]AS, which we refer to as Pillar[6]MaxQ along with analogues P[5]AS and P[7]AS toward guests 1–18. The ultratight binding affinity of P[5]AS and P[6]AS toward quaternary (di)ammonium ions renders them prime candidates for in vitro and in vivo non-covalent bioconjugation, for imaging and delivery applications, and as in vivo sequestration agents.

Host-guest interaction of nitroxide radicals with water-soluble pillar[6]arenes

The host-guest interaction of nitroxide radicals with water-soluble pillar[n]arenes was studied for the first time by electron paramagnetic resonance spectroscopy and NMR spectroscopy. Our results showed that this interaction strongly depended on the 4-su

Cation templated improved synthesis of pillar[6]arenes

Improved high yield syntheses of the larger pillar[6]arenes (P[6]) bearing different alkoxy substituents through cation templated syntheses using a series of small organic and organometallic cations is reported. Yields of P[6] up to 38% and P[6]/P[5] ratios as high as 5:1 were achieved.

Efficient inhibition of human papillomavirus 16 L1 pentamer formation by a carboxylatopillarene and a p-sulfonatocalixarene

Pillarenes and calixarenes showed obvious inhibition of HPV16 L1 pentamer formation via their selective binding to Arg and Lys residues at the monomer interface, which was reversible after the release of cyclic arenes. Pillarenes are more effective than calixarenes in terms of the inhibition efficiency, attributing to the different kinetics and binding affinity. The Royal Society of Chemistry 2014.

Synthesis of pillar[5]arenes with a PH-containing fragment

The reactions of phosphorus(III) chloride and 2-chloro-1,3,2-dioxaphospholane with monohydroxypillar[5]arene afforded for the first time the corresponding PH-phosphonates. It was found that the newly formed P–O(Ar) bond is characterized by considerably reduced reactivity, which was rationalized by essential shielding of the phosphorus atom by the pillar[5]arene macrocycle. The pillar[5]arene scaffold stabilizes the highly reactive PIII–Cl fragment, so that the formation of macrocyclic dichlorophosphite can be detected under normal conditions.