Urea and thiourea based anion receptors in solution and on polymer supports

Byrne, Sean; Mullen, Kathleen M.

doi:10.1080/10610278.2017.1394462

Cited by 10 publications

(7 citation statements)

References 32 publications

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“…One of the strategies used to solve these problems is to support anion receptors in different materials like Tentagel resins . These copolymers, which consist of a polystyrene (PS) and polyethylene glycol (PEG), can be swelled in almost all solvents due to PEG so that the hydrophilic and hydrophobic properties are given to the resin. , …”

Section: Introductionmentioning

confidence: 99%

Optical Anion Receptors with Urea/Thiourea Subunits on a TentaGel Support

et al. 2021

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Two simple chemosensors with urea (L1) and thiourea (L2) groups were synthesized and studied by different spectroscopic techniques. Both receptors can sense acetate (Ac – ), dihydrogen phosphate (H 2 PO 4 – ), and fluoride (F – ) anions, accompanied by changes in UV–vis and 1 H NMR spectra, and an optical response is observed as a color change of the solutions due to deprotonation and hydrogen-bonding processes. Also, L1 and L2 were supported on TentaGel resins (R1 and R2), and their fluoride-sensing properties in DMSO and water solutions were studied. Interestingly, R2 can sense fluoride ions in sample solutions of 100% water.

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Section: Introductionmentioning

confidence: 99%

Optical Anion Receptors with Urea/Thiourea Subunits on a TentaGel Support

et al. 2021

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“…Urea is commonly used as a neutral recognition motif that effectively provides two parallel hydrogen bond donors for binding oxyanions but primarily in organic solvents or mixtures of organic solvents and water. 45,[70][71][72][73][74][75][76][77][78][79] However, through encapsulation in a POP, here we show in a rare instance that urea is capable of hydrogen bonding with anionic guests in pure water. 70,80 As a proof-of-concept, we tested the ability of Urea-POP-1 to recognize organic dyes through adsorption assays that contain phosphonate (R-PO3 2-), sulfonate (R-SO3 -), and carboxylate (R-COO -) anions.…”

Section: Introductionmentioning

confidence: 56%

A Neutral Porous Organic Polymer Host for the Recognition of Anionic Dyes in Water

Ong¹,

Smaldone²,

Dodani³

2020

Preprint

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Neutral hosts for the recognition of anionic guests in water remain underdeveloped due to the inherent thermodynamic barrier for desolvation. As a new strategy to address this challenge, we have repurposed crosslinked porous organic polymers (POPs) as hosts. This polymer architecture affords a hydrophobic environment with a densely packed array of urea hydrogen bond donors to cooperatively promote anion desolvation and recognition in water. As a proof-of-concept, we demonstrate through adsorption assays that the resulting Urea-POP-1 can discriminate between structurally different dyes containing phosphonate, sulfonate, and carboxylate anions. Moreover, when compared to Methyl-POP-1, a control POP lacking hydrogen bond donors, we find that recognition is not exclusively driven by the hydrophobicity of the dyes but through selective hydrogen bonding interactions of the urea sidechains with the anionic functional groups. This starting point sets the stage to exploit the modularity of our design to build a family of neutral polymer hosts with tunable pore sizes and anion preferences for fundamental investigations and targeted applications.

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“…43 On the other side of the axle, Py-U, a pyrene-urea linked with an azide functional group for the cycloaddition, was formed from the reaction of 1-aminopyrene with compound S5 in 61% yield (Scheme S3, Supporting Information). 44 The target [2]rotaxane P1 was obtained in a one-pot synthesis by threading-followed-by-capping approach through the formation of a pseudo rotaxane from alkyne compound S4 and tbutylcalix [4]arene macrocycle S7 under highly dilute condition in dry DCM. For subsequent capping, an azide group containing pyrene bulky stopper was introduced to the pseudo rotaxane solutions through the copper(I)-catalyzed azide− alkyne cycloaddition (CuAAC) to prevent the macrocycle S7 from slipping off the axle, yielding [2]rotaxane P1 in 16% yield (see Scheme 1).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Diversiform Nanostructures Constructed from Tetraphenylethene and Pyrene-Based Acid/Base Controllable Molecular Switching Amphiphilic [2]Rotaxanes with Tunable Aggregation-Induced Static Excimers

Arumugaperumal

Shellaiah

Srinivasadesikan

et al. 2020

ACS Appl. Mater. Interfaces

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Dual-emissive tetraphenylethene (TPE) and pyrene-containing amphiphilic molecules are of great interest because they can be integrated to form stimuli responsive materials with various biological applications. Herein, we report the study of mechanically interlocked molecules (MIMs) with aggregation-induced static excimer emission (AISEE) property through a series of TPE and pyrene-based amphiphilic [2]rotaxanes, where tbutylcalix[4]arene with hydrophobic nature was used as the macrocycle. Evidently, by adorning TPE and pyrene units in [2]rotaxanes P1, P2, P1-b, and P2-b, they display remarkable emission bands in 70% of water fraction (f w ) in tetrahydrofuran (THF)/water mixture, which could be attributed to the restricted intramolecular rotation of phenyl groups, whereas prominent blue-shifted excimer emission of pyrene started to appear as f w reached 80% for P1 and 90% for P1-b, P2, and P2-b, which was ascribed to the favorable π−π stacking and hydrophobic interactions of the pyrene rings that enabled their static excimer formation. The well-defined distinct amphiphilic nanostructures of [2]rotaxanes including hollowspheres, mesoporous nanostructures, spheres, and network linkages can be driven smoothly depending on the molecular structures and their aggregated states in THF/water mixture. These fascinating diversiform nanostructures were mainly controlled by the skillful manner of reversible molecular shuttling of t-butylcalix[4]arene macrocycle and also the interplay of multinoncovalent interactions. To further understand the aggregation capabilities of [2]rotaxanes, the human lung fibroblasts (MRC-5) living cell incubated with either P1, P2, P1-b, or P2-b was studied and monitored by confocal laser scanning microscopy. The AISEE property was achieved at an astonishing level by integrating TPE and pyrene to MIM-based reversible molecular switching [2]rotaxanes; furthermore, distinct nanostructures, especially hollowspheres and mesoporous nanostructures, were observed, which are rarely reported in the literature but are highly desirable for future applications.

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Urea and thiourea based anion receptors in solution and on polymer supports

Cited by 10 publications

References 32 publications

Optical Anion Receptors with Urea/Thiourea Subunits on a TentaGel Support

Optical Anion Receptors with Urea/Thiourea Subunits on a TentaGel Support

A Neutral Porous Organic Polymer Host for the Recognition of Anionic Dyes in Water

Diversiform Nanostructures Constructed from Tetraphenylethene and Pyrene-Based Acid/Base Controllable Molecular Switching Amphiphilic [2]Rotaxanes with Tunable Aggregation-Induced Static Excimers

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