The charge-assisted hydrogen-bonded organic framework (CAHOF) self-assembled from the conjugated acid of tetrakis(4-aminophenyl)methane and 2,6-naphthalenedisulfonate as a new class of recyclable Brønsted acid catalysts

Kuznetsova, S. A.; Gak, Alexander S.; Nelyubina, Yulia V.; Larionov, Vladimir A.; Li, Han; North, Michael; Zhereb, V. P.; Smol’yakov, Alexander F.; Дмитриенко, Артем О.; Medvedev, Michael G.; Gerasimov, Igor S.; Saghyan, Ashot S.; Belokoń, Yuri N.

doi:10.3762/bjoc.16.99

Cited by 10 publications

(20 citation statements)

References 45 publications

(72 reference statements)

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“…83 Similarly, for a recently reported charge-assisted HOF, F-1a, the presence of catalytically active Brønsted acid sites makes it an excellent heterogeneous catalyst to catalyze the ring-opening of epoxides and the Diels−Alder reaction between cyclopentadiene and methyl vinyl ketone. 113 ■ BIOLOGICAL APPLICATIONS Since most HOFs are metal-free, they exhibit considerable biocompatibility and low toxicity, thus being excellent candidates for biological applications. As mentioned above, using a pyrene-based linker, Yin et al reported the synthesis of a highly stable HOF, PFC-1 (Figure 8a).…”

Section: ■ Fluorescent Sensingmentioning

confidence: 99%

“…In addition, 1-Ni can also be used for catalyzing the asymmetric F–C alkylations of indole and aryl aldimines . Similarly, for a recently reported charge-assisted HOF, F-1a, the presence of catalytically active Brønsted acid sites makes it an excellent heterogeneous catalyst to catalyze the ring-opening of epoxides and the Diels–Alder reaction between cyclopentadiene and methyl vinyl ketone …”

Section: Heterogeneous Catalysismentioning

confidence: 99%

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Hydrogen-Bonded Organic Frameworks as a Tunable Platform for Functional Materials

et al. 2020

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As a novel class of porous crystalline materials, hydrogen-bonded organic frameworks (HOFs), self-assembled from organic or metal−organic building blocks through intermolecular hydrogen-bonding interactions, have attracted more and more attention. Over the past decade, a number of porous HOFs have been constructed through judicious selection of H-bonding motifs, which are further enforced by other weak intermolecular interactions such as π−π stacking and van der Waals forces and framework interpenetration. Since the H-bonds are weaker than coordinate and covalent bonds used for the construction of metal−organic frameworks (MOFs) and covalent organic frameworks (COFs), HOFs have some unique features such as mild synthesis condition, solution processability, easy healing, and regeneration. These features enable HOFs to be a tunable platform for the construction of functional materials. Here, we review the H-bonding motifs used for constructing porous HOFs and highlight some of their applications, including gas separation and storage, chiral separation and structure determination, fluorescent sensing, heterogeneous catalysis, biological applications, proton conduction, photoluminescent materials, and membrane-based applications.

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Section: ■ Fluorescent Sensingmentioning

confidence: 99%

Section: Heterogeneous Catalysismentioning

confidence: 99%

Hydrogen-Bonded Organic Frameworks as a Tunable Platform for Functional Materials

et al. 2020

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“…Meanwhile, the diversity of hydrogen bonds provides more possibilities for the construction of the frameworks of crystalline organic salts. [48][49][50][51][52][53][68][69][70][71] A series of guanidinium sulfonate (GS) frameworks with various elegant and diversified architectures, like lamellar, cylindrical, and cubic ( Figure 5), have been synthesized from guanidinium cations and organosulfonate anions through salt bridges by Ward and co-workers. [48][49][50][51][52][53] These crystalline organic salts were achieved by rational design of the size and the symmetry of the tectons and assembly.…”

Section: Organic Acid Tecton With Sulfonate Groupmentioning

confidence: 99%

“…Meanwhile, the diversity of hydrogen bonds provides more possibilities for the construction of the frameworks of crystalline organic salts. [ 48–53,68–71 ]…”

Section: Crystalline Porous Organic Saltsmentioning

confidence: 99%

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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“…[ 14‐16 ] To achieve this goal, constructing the charge‐assisted hydrogen bonding organic networks (CAHONs) with oppositely charged components and multiple hydrogen‐bonding interactions has considered as a powerful strategy by virtue of the electrostatic interactions between discrete cations and anions. [ 2,17‐19 ] However, the research on CAHONs is still rare, so we urgently need to synthesize more CAHONs and explore their potential properties in depth.…”

Section: Background and Originality Contentmentioning

confidence: 99%

A Photo‐Responsive Charge‐Assisted Hydrogen‐Bonded Organic Network with Ultra‐Stable Viologen Radicals

Shen

Yang

et al. 2021

Chin. J. Chem.

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Comprehensive Summary Hydrogen‐bonded organic networks (HONs) have attracted intense research interest due to their mild synthesis conditions, good solvent processability and strong reproducibility. Most HONs are constructed by electrically neutral organic ligands through intermolecular interactions such as weak hydrogen bonding, π‐π stacking. But there are a few charge‐assisted hydrogen‐bonding networks (CAHONs) constructed by oppositely charged organic components. Under hydrothermal conditions, we successfully synthesized a 3D CAHON (H2CV)(H2BTEC) (1) constructed by H2CV (CV = N,N′‐4,4′‐bipyridine dipropionate) and H4BTEC (H4BTEC = 1,2,4,5‐benzenetetracarboxylic acid) through multiple charge‐assisted hydrogen bonding. Upon soft X‐ray, ultraviolet light or sunlight irradiation under ambient conditions, 1 quickly changes from colorless to blue (1P), and kinetic calculations show that its photochromism meets first‐order dynamics. Interestingly, the colored crystals 1P with long‐lived colored radicals will not fade after being placed for more than two months at room temperature in air, owing to the fact that the photogenerated viologen radicals can be stabilized by the abundant hydrogen bonds, the coplanar pyridinium rings and the slow electron‐hole recombination. Moreover, 1 is a typical direct band gap semiconductor, evidenced by the calculated band gap of 3.24 eV, in agreement with the experimental value of 3.40 eV. In view of its strong colored stability, 1 is designed for distinctive inkless printing.

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The charge-assisted hydrogen-bonded organic framework (CAHOF) self-assembled from the conjugated acid of tetrakis(4-aminophenyl)methane and 2,6-naphthalenedisulfonate as a new class of recyclable Brønsted acid catalysts

Cited by 10 publications

References 45 publications

Hydrogen-Bonded Organic Frameworks as a Tunable Platform for Functional Materials

Hydrogen-Bonded Organic Frameworks as a Tunable Platform for Functional Materials

Crystalline Porous Organic Salts: From Micropore to Hierarchical Pores

A Photo‐Responsive Charge‐Assisted Hydrogen‐Bonded Organic Network with Ultra‐Stable Viologen Radicals

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