Application of Cocrystallization for the Separation of <i>C</i>-Ethylresorcin[6]arene from <i>C</i>-Ethylresoricn[4]arene

Jiang, Shan; Patil, Rahul S.; Barnes, Charles L.; Atwood, Jerry L.

doi:10.1021/acs.cgd.7b00691

Cited by 3 publications

(2 citation statements)

References 40 publications

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“…Compound 21 and A self‐assemble to form a doubly interpenetrated 3D SOF 21A in the solid state, which possesses box‐like cavities capable of binding two molecules of ferrocene. However, self‐assembly of C‐alkylresorcin[4]arenes 21 or 23 with the spacer B yielded continuous 1D wavelike and 1D lateral SOFs …”

Section: Resorcinarene‐based Comsmentioning

confidence: 99%

Supramolecular‐Macrocycle‐Based Crystalline Organic Materials

et al. 2019

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macrocycles. They have been also employed to modify the surface properties of metal nanoparticles via noncovalent host−guest interactions, [31] covering their applications in drug delivery, [32] highly sensitive sensors, [33] selective catalysis, [34] and so on.In addition to their intensive applications based on their host−guest chemistry, macrocycles have also been used as building blocks to construct solid materials including porous organic polymers (POPs), [35,36] metal-organic frameworks (MOFs), [37][38][39][40][41][42][43] and crystalline organic materials (COMs). [44][45][46][47][48][49][50][51][52][53][54][55][56][57] Particular attention should be paid to COMs, a class of organic materials featuring facile preparation, high crystallinity, structural diversity, chemical stability, solution-processability, etc. [58][59][60][61][62][63][64][65][66][67][68][69][70] Different from MOFs that are composed of both inorganic (metal ions) and organic species (organic ligands) through coordination, COMs refer to a kind of crystalline materials composed of pure organics connected by either covalent or noncovalent bonds. [71][72][73] For COMs connected by noncovalent bonds, the typical materials are organic molecular crystals with intriguing properties such as semiconductor, [53] porosity, [68] etc. Owing to the inefficient packing of organic building blocks in the crystal state, some molecular crystals display extrinsic porosity, which are often termed as hydrogen-bonded organic frameworks (HOFs) [74,75] or supramolecular organic frameworks (SOFs). [76][77][78][79][80] For COMs connected by covalent bonds, typical materials are crystalline covalent organic frameworks (COFs), which were firstly reported in 2005 by Yaghi and co-workers [44] Benefitting from rigid chemical bonds and building blocks, COFs show permanent and well-ordered porosity. [45][46][47][48] Supramolecular-macrocycle-based COMs, a class of COMs with macrocycles as the main building blocks, have drawn particular attention in recent years. According to their components, supramolecular-macrocycle-based COMs can be classified into two main categories, the ones composed of pure macrocycles and the others consisting of macrocycles and other simple organic building blocks. Owing to their prefabricated cavities of a certain type, some of macrocycle-based COMs exhibit intrinsic microporosity for guest adsorption in the solid state. On the other hand, the extrinsic porosity of some macrocyclebased COMs may form due to the inefficient packing of these rigid macrocyclic molecules in the crystalline state. In certain circumstances, both intrinsic and extrinsic microporosity can be created in a single lattice of a certain COM, thus leading to Supramolecular macrocycles are well known as guest receptors in supramolecular chemistry, especially host−guest chemistry. In addition to their wide applications in host−guest chemistry and related areas, macrocycles have also been employed to construct crystalline organic materials (COMs) owing to their particular structur...

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Section: Resorcinarene‐based Comsmentioning

confidence: 99%

Supramolecular‐Macrocycle‐Based Crystalline Organic Materials

et al. 2019

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“…The major structural feature of resorcinarenes is the electron-rich cavity, formed by the circular intramolecular O···H–O hydrogen bonding interactions between adjacent resorcinol units that can bind neutral and cationic guests through C–H···π, cation···π, and/or cooperative H-bond interactions . In the case of guest shape and size mismatch, the host’s cavity stabilizes either by self-inclusion − or solvent encapsulation. , Exo-guest complex formation arises often via competitive H-bond interactions resulting in cocrystal complexes. ,, The situation becomes even more complex when the H-G systems are in equilibrium with metal ions or highly H-bond competitive anions and the hosts are prevented from forming guest-inclusion complexes. Sodiumsulfonatomethyleneresorcinarene is an example of a host that can interact with guests via multiple functionalities (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Host–Guest Interactions of Sodiumsulfonatomethyleneresorcinarene and Quaternary Ammonium Halides: An Experimental–Computational Analysis of the Guest Inclusion Properties

Twum

Rautiainen

et al. 2020

Crystal Growth & Design

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Supramolecule-Driven Host–Guest Co-Crystallization of Cyclic Polyphenols with Anti-Fibrotic Pharmaceutical Drug

Panigrahi

Mayhan

Dar

et al. 2023

Crystal Growth & Design

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Host–guest complexes are of interest as supramolecular drugs in pharmaceutical sciences because the activity of antibacterial agents can be enhanced upon complexation with various cyclic oligomers or metal ions, with some complexes possessing higher healing properties than the parent drugs. Herein, to develop a microbiologically potent supramolecular drug, we investigated the complexation of macrocyclic hosts (resorcinarenes and β-cyclodextrin) with pirfenidone (PFD), an FDA-approved antifibrotic drug containing an antibacterial pyridone core. Electronic structure calculations gave insights into the interactions in the host–PFD complexes. Further, complex formation and clinical activities were investigated using spectroscopic techniques and in vitro measurements of antibacterial activity against Gram-positive and Gram-negative bacteria. An unprecedented interplay between the antibacterial activity of the polyphenolic resorcinarene hosts and their ability to interact chemically with PFD was found to improve the overall antibacterial activity of PFD. These results could revolutionize the use of synthetically modifiable resorcinarene and their analogues for fine-tuning the clinical behavior of drugs.

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Application of Cocrystallization for the Separation of C-Ethylresorcin[6]arene from C-Ethylresoricn[4]arene

Cited by 3 publications

References 40 publications

Supramolecular‐Macrocycle‐Based Crystalline Organic Materials

Supramolecular‐Macrocycle‐Based Crystalline Organic Materials

Host–Guest Interactions of Sodiumsulfonatomethyleneresorcinarene and Quaternary Ammonium Halides: An Experimental–Computational Analysis of the Guest Inclusion Properties

Supramolecule-Driven Host–Guest Co-Crystallization of Cyclic Polyphenols with Anti-Fibrotic Pharmaceutical Drug

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