Supramolecular anion recognition in water: synthesis of hydrogen-bonded supramolecular frameworks

Morshedi, Mahbod; Thomas, Matthias; Tarzia, Andrew; Doonan, Christian J.; White, Nicholas G.

doi:10.1039/c7sc00201g

Cited by 91 publications

(136 citation statements)

References 71 publications

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“…[12] Building upon this result,w eh ypothesized that as imilars tructure could be prepared using the extended tecton TBA 2 ·biphenyldicarboxylate. [12] Building upon this result,w eh ypothesized that as imilars tructure could be prepared using the extended tecton TBA 2 ·biphenyldicarboxylate.…”

Section: Framework Series A(tetraamidinium 1 4 + + and Dicarboxylates)mentioning

confidence: 97%

“…[12] pared from two tetravalent tectons, ast hese may be even more robust. [12] pared from two tetravalent tectons, ast hese may be even more robust.…”

Section: Framework Series C( Tetraamidinium and Tetracarboxylates)mentioning

confidence: 99%

“…[3c, 11] Notably,W ard has used the interaction between unsubstituted guanidinium cations and polysulfonate anionst op repare aw ide range of open materials including cylindrical and lamellar architectures and networkedc ages. [12,13] By considering polyamidinium and di/polycarboxylate units as node-and-linker motifs, we hypothesized that this system may offer ar oute to design and synthesize af amily of frameworks and thus overcome one of the major remaining challenges in HOF chemistry. We recentlyr eported that tetraamidinium cations and dicarboxylate anions could be combined to prepare an open diamondoid framework in water.…”

Section: Introductionmentioning

confidence: 99%

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Molecular Tectonics: A Node‐and‐Linker Building Block Approach to a Family of Hydrogen‐Bonded Frameworks

Boer

Morshedi

Tarzia

et al. 2019

Chemistry A European J

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While numerous hydrogen-bonded organic frameworks (HOFs) have been reported, typically these cannot be prepared predictablyo ri namodular fashion. In this work, we report af amilyo fn ine diamondoid crystalline porous frameworksa ssembled via hydrogen bondingb etween polyamidinium and poly-carboxylate tectons. The frameworks are prepared at room temperature in either water or water/ alcoholm ixtures. Importantly,b oth the cationic and anionic components can be varied and additional functionality can be incorporated into the frameworks, which show good stability including to prolonged heating in DMSO or water.Supporting information and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

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Section: Framework Series A(tetraamidinium 1 4 + + and Dicarboxylates)mentioning

confidence: 97%

“…[12] pared from two tetravalent tectons, ast hese may be even more robust. [12] pared from two tetravalent tectons, ast hese may be even more robust.…”

Section: Framework Series C( Tetraamidinium and Tetracarboxylates)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Molecular Tectonics: A Node‐and‐Linker Building Block Approach to a Family of Hydrogen‐Bonded Frameworks

Boer

Morshedi

Tarzia

et al. 2019

Chemistry A European J

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“… Examples of self‐assembled structures prepared using charge‐assisted hydrogen bonds: a) Wais Hosseini's synthesis of 1D supramolecular polymers, b) general representation of Ward's synthesis of a family of guanidinium–sulfonate frameworks, and c) White's synthesis of amidinium–carboxylate frameworks …”

Section: Introductionmentioning

confidence: 99%

“…Ward's group has pioneered the assembly of simple guanidinium cations with polysulfonate molecules to give ready access to a large family of guanidinium–sulfonate frameworks (Figure b), many of which encapsulate organic guest molecules . Inspired by these studies, we recently reported the synthesis of supramolecular organic frameworks in water based on the favorable interactions between a tetraamidinium cation and terephthalate anions (Figure c) …”

Section: Introductionmentioning

confidence: 99%

Hydrogen bond‐Driven Self–Assembly between Amidinium Cations and Carboxylate Anions: A Combined Molecular Dynamics, NMR Spectroscopy, and Single Crystal X‐ray Diffraction Study

Thomas

Lagones

Judd

et al. 2017

Chemistry An Asian Journal

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Ac ombination of molecular dynamics (MD), NMR spectroscopy,a nd single crystal X-ray diffraction (SCXRD) techniquesw as used to probe the self-assemblyo fparaand meta-bis(amidinium) compoundsw ith para-, meta-, and ortho-dicarboxylates. Good concordancew as observed between the MD and experimental results. In DMSO solution, the systemsf orm several rapidly exchanging assemblies,i n part because ar ange of hydrogen bondingi nteractions is possible between the amidinium and carboxylate moieties. Upon crystallization, the majority of the systemsf orm 1D supramolecular polymers, which are held together by short NÀH···Oh ydrogen bonds.

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Crystalline Porous Organic Salts: From Micropore to Hierarchical Pores

et al. 2020

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fluids at the molecular level to achieve storage, separation, transformation and other functions and have aroused a wide range of interests from basic to applied research. [1,2] For instance, crystalline zeolitic materials with uniform and tuneable pore architecture have been widely utilized to facilitate various processes such as catalytic reactions, adsorption-separation, and ion-exchange. The advantageous features of zeolites include large surface areas and pore volume, tuneable porosity, controllable compositions, superior stability, and fine shape-selectivity of guest molecules. [3-6] Inspired by the success of zeolites, the development of hybrid porous materials (e.g., metal-organic frameworks (MOFs)), [7] organic porous materials (e.g., hyper crosslinked polymer (HCPs), [8,9] conjugated microporous polymers (CMPs), [10,11] polymers of intrinsic microporous (PIMs), [12] porous aromatic frameworks (PAFs), [13] covalent organic frameworks (COFs), [14,15] etc.) had a booming growth in last years, which greatly expanded the applications of porous materials with strengthened material functionality. Though recent advances of the abovementioned hybrid/organic porous materials provide some examples possessing high polar pores, [16-23] the synthesis of functional porous materials with the capability of adsorption, recognition and transport of high polar molecules is still highly challenging. In the history of porous materials, permanent porosity is an important criterion to distinguish porous materials from common network compounds composed of similar linkers and building units. [24-27] The permanent porosity refers to the voids of the framework compound after stripping guest molecules, which are permanently and reversibly accessible for alternative guest molecules. The permanent porosity of materials is usually verified by the widely used reversible gas adsorption method such as nitrogen or carbon dioxide adsorption. [27] Meanwhile, the obtained gas sorption isotherms can be applied to the determination of surface area and other porous characteristics using the different data treatment methods such as Brunauer-Emmett-Teller (BET), Dubinin-Astakhov (DA) methods and so on. In the case of large amount of crystalline frameworks constructed by organic salt bond, only those species contain such kind of permanent porosity can be referred to really "porous" or "open framework," i.e., CPOSs. As-synthesized crystalline organic salts (COSs) which contain guest molecules and have no accessible porosity due to the Crystalline porous organic salts (CPOSs), as an emerging class of porous organic materials, combining the uniform microporous system and distinct polarized channels, have become a highly evolving field of important current interest. The unique ionic bond of a CPOS endows the confined channels with high polarity, making CPOSs distinct from other organic frameworks. CPOSs show many fascinating properties, such as proton conductivity and fast transport of polar molecules, which involve the interaction between highly pola...

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Supramolecular anion recognition in water: synthesis of hydrogen-bonded supramolecular frameworks

Abstract: Charge-assisted hydrogen bonds between a tetratopic receptor and terephthalate anions assemble a switchable supramolecular framework material in water.

Cited by 91 publications

References 71 publications

Molecular Tectonics: A Node‐and‐Linker Building Block Approach to a Family of Hydrogen‐Bonded Frameworks

Molecular Tectonics: A Node‐and‐Linker Building Block Approach to a Family of Hydrogen‐Bonded Frameworks

Hydrogen bond‐Driven Self–Assembly between Amidinium Cations and Carboxylate Anions: A Combined Molecular Dynamics, NMR Spectroscopy, and Single Crystal X‐ray Diffraction Study

Crystalline Porous Organic Salts: From Micropore to Hierarchical Pores

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