Exploration of relative π-electron localization in naphthalene aromatic rings by C–H⋯π interactions: experimental evidence, computational criteria, and database analysis

Samie, Ali; Salimi, Alireza; Garrison, Jered C.

doi:10.1039/c9ce00929a

Cited by 10 publications

(3 citation statements)

References 64 publications

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“…Nevertheless, a comparison of the ligand geometries in the investigated MOFs reveals that the disorder of the TPE core and one external phenylene ring in 1-F is analogous to that of 1 , which means that the fluorine atoms exert minor intramolecular steric effects on the relative changes of ligand geometry in the case of the noncontracted networks (see Figure S22). Furthermore, looking into the type of intermolecular interactions between subframeworks in 1 and 1-F , the crystal structures show the presence of several weak π···H–C arom and F···H–C arom interactions (characteristic distances from 2.09 to 2.84 Å). − …”

Section: Resultsmentioning

confidence: 99%

Postsynthetic Framework Contraction Enhances the Two-Photon Absorption Properties of Pillar-Layered Metal–Organic Frameworks

et al. 2020

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Aggregation-induced emission (AIE) dyes have been shown to be a potential ligand class for multiphoton absorbing metal–organic frameworks (MPA-MOFs); however, the influence of framework flexibility on the local ligand conformation and its ramifications on the nonlinear absorption properties of this material class have sparsely been understood. In this study, we systematically investigate the two-photon absorption properties of two pillar-layered MOFs comprising tetraphenylethylene AIE ligands and compare the results to the organic ligand in crystal form, using a combination of linear and nonlinear optical characterization methods and electronic-structure calculations. We demonstrate that self-confining the AIE ligand is key to enhance the nonlinear optical absorption properties, as a structure transformation to contracted frameworks strongly increases the two-photon absorption response, which can be addressed by specific ligand substitution. Our results have important implications on the design of MPA-MOFs and provide synthetic guidelines not only from a fundamental point of view but also application-wise.

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Section: Resultsmentioning

confidence: 99%

Postsynthetic Framework Contraction Enhances the Two-Photon Absorption Properties of Pillar-Layered Metal–Organic Frameworks

et al. 2020

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“…The intramolecular interaction between keto and enol inside the CUR molecule is presented with a green color in Figure c. The main intermolecular interactions of O–H···O (magenta), C–H···O (blue), and C–H···π (yellow) , between the two molecules also represented in Figures c. Correspondingly, formation of hydrogen bonding between the hydroxyl functional groups of PYR and the keto fragment of CUR was one of the main reasons for the cocrystal formation.…”

Section: Resultsmentioning

confidence: 89%

Accelerated Wound Healing with a Diminutive Scar through Cocrystal Engineered Curcumin

Samie,

Alavian,

Vafaei-Pour

et al. 2023

Mol. Pharmaceutics

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Pharmaceutical cocrystals (Regulatory Classification of Pharmaceutical Co-Crystals Guidance for Industry; Food and Drug Administration, 2018) are crystalline solids produced through supramolecular chemistry to modulate the physicochemical properties of active pharmaceutical ingredients (APIs). Despite their extensive development in interdisciplinary sciences, this is a pioneering study on the efficacy of pharmaceutical cocrystals in wound healing and scar reducing. Curcumin−pyrogallol cocrystal (CUR−PYR) was accordingly cherry-picked since its superior physicochemical properties adequately compensate for limitative drawbacks of curcumin (CUR). CUR− PYR has been synthesized by a liquid-assisted grinding (LAG) method and characterized via FT-IR, DSC, and PXRD analyses. In vitro antibacterial study indicated that CUR−PYR cocrystal, CUR+PYR physical mixture (PM), and PYR are more effective against both Gram-negative (Pseudomonas aeruginosa and Escherichia coli) and Gram-positive (Staphylococcus aureus and Bacillus subtilis) bacteria in comparison with CUR. In vitro results also demonstrated that the viability of HDF and NIH-3T3 cells treated with CUR−PYR were improved more than those received CUR which is attributed to the effect of PYR in the form of cocrystal. The wound healing process has been monitored through a 15 day in vivo experiment on 75 male rats stratified into six groups: five groups treated by CUR−PYR+Vaseline (CUR−PYR.ung), CUR+PYR+Vaseline (CUR+PYR.ung), CUR+Vaseline (CUR.ung), PYR+Vaseline (PYR.ung), and Vaseline (VAS) ointments and a negative control group of 0.9% sodium chloride solution (NS). It was revealed that the wounds under CUR−PYR.ung treatment closed by day 12 postsurgery, while the wounds in other groups failed to reach the complete closure end point until the end of the experiment. Surprisingly, a diminutive scar (3.89 ± 0.97% of initial wound size) was observed in the CUR−PYR.ung treated wounds by day 15 after injury, followed by corresponding values for PYR.ung (12.08 ± 2.75%), CUR+PYR.ung (13.89 ± 5.02%), CUR.ung (16.24 ± 6.39%), VAS (18.97 ± 6.89%), and NS (20.33 ± 5.77%). Besides, investigating histopathological parameters including inflammation, granulation tissue, reepithelialization, and collagen deposition signified outstandingly higher ability of CUR−PYR cocrystal in wound healing than either of its two constituents separately or their simple PM. It was concluded that desired solubility of the prepared cocrystal was essentially responsible for accelerating wound closure and promoting tissue regeneration which yielded minimal scarring. This prototype research suggests a promising application of pharmaceutical cocrystals for the purpose of wound healing.

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“…There are extended noncovalent, π-π, interactions between parallel Bpy rings on adjacent chains with a separation of 3.984 Å. 38 The asymmetric unit contains [(BPy) 2 MnCl 2 ] and water molecules, which are connected with intermolecular hydrogen bonds (Table 3), forming three-dimensional network (Olw-O21 2.775 (8) Å) (Figure 1B). Also, the water molecule interacts with the chloride ligands (Olw-CI 3.293 (3) and 3.258 (3) Å).…”

Section: Dft Calculationsmentioning

confidence: 99%

A newly synthesized bipyridine‐containing manganese( II ) complex immobilized on graphene oxide as active electrocatalyst for hydrogen gas production from alkaline solutions: Experimental and theoretical studies

Alharthi

Ibrahim

El‐Sheshtawy

et al. 2022

Intl J of Energy Research

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A new bipyridine-containing manganese (II) complex, namely [(BPy) 2 MnCl 2 ]Á 0.5H 2 O (MnC), was synthesized and characterized. Spectral and X-ray structural features revealed that MnC has an octahedral environment around Mn(II). Graphene oxide (GO) was noncovalently functionalized with the MnC.MnC-and (MnC/GO)-modified glassy carbon (GC) interfaces with different loading densities (0.2, 0.4, 0.8, and 1.0 mg cm À2 ) were tested as electrocatalysts for efficient generation of H 2 in 0.1 M KOH solution. The GC-MnC catalysts exhibited high electrocatalytic activity for the HER, which enhances upon increasing the catalyst's loading density. The GC-MnC catalyst's HER activity, at any tested loading density, was found to further increase upon supporting MnC on GO. The best performing electrocatalyst, namely GC-(MnC/GO) with a loading density of 1.0 mg cm À2 , exhibited high HER catalytic activity with a low onset potential value of À22 mV vs. reference hydrogen electrode (RHE) and a high exchange current density of 0.75 mA cm À2 . It delivered a current density of 10 mA cm À2 at an overpotential value of 119 mV. In addition, it recorded a Tafel slope value of À114 mV dec À1 . These HER electrochemical kinetic parameters approached those measured here for the commercial Pt/C under the same operating conditions (À10 mV vs. RHE, 0.88 mA cm À2 , 113 mV dec À1 , and 110 mV to yield a current density of 10 mA cm À2 ) and also comparable to the most active molecular electrocatalysts for H 2 generation from aqueous alkaline electrolytes published in the literature. The long-term stability of the best performing electrocatalyst, namely GC-MnC

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Exploration of relative π-electron localization in naphthalene aromatic rings by C–H⋯π interactions: experimental evidence, computational criteria, and database analysis

Abstract: In C–H⋯π interaction, the relative π-electron localization in aromatic ring led to the change of contact position from centre to edges of the ring (C–H⋯πe) which was confirmed by experimental evidences, computational criteria, and database analysis.

Cited by 10 publications

References 64 publications

Postsynthetic Framework Contraction Enhances the Two-Photon Absorption Properties of Pillar-Layered Metal–Organic Frameworks

Postsynthetic Framework Contraction Enhances the Two-Photon Absorption Properties of Pillar-Layered Metal–Organic Frameworks

Accelerated Wound Healing with a Diminutive Scar through Cocrystal Engineered Curcumin

A newly synthesized bipyridine‐containing manganese( II ) complex immobilized on graphene oxide as active electrocatalyst for hydrogen gas production from alkaline solutions: Experimental and theoretical studies

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