Intermolecular Hydrogen Bonding Directed by Aryl–Perfluoroaryl π–π Stacking Interactions

Alfuth, Jan; Kazimierczuk, Katarzyna; Połoński, Tadeusz; Olszewska, Teresa

doi:10.1021/acs.cgd.3c00676

Cited by 6 publications

(1 citation statement)

References 89 publications

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“…The reduced stacking distance means that the π–π interaction intensity is strengthened because of the modification of the local structure. 51–53 The strengthening of π–π interaction alters the charge distribution of organic molecules. To study the local charge distribution in detail, the charge densities of a reduced cluster in 23-CdCl and 23-ZnCl crystals were calculated based on NCI analysis.…”

Section: Resultsmentioning

confidence: 99%

Tailoring the π–π stacking interaction among organic cations in hybrid metal halide crystals towards tunable light emission

Zhang,

Lin,

Guo

et al. 2024

J. Mater. Chem. C

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Section: Resultsmentioning

confidence: 99%

Tailoring the π–π stacking interaction among organic cations in hybrid metal halide crystals towards tunable light emission

Zhang,

Lin,

Guo

et al. 2024

J. Mater. Chem. C

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Synthesis of Diels–Alder bond and hydrogen bond synergistic shape memory self‐healing polyurethane elastomers

Zhang,

Wang,

Cao

et al. 2023

J of Applied Polymer Sci

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Self‐healing materials exhibit the ability to repair damage and restore their function. Shape memory assisted self‐healing (SMASH) materials are smart materials that automatically close localized microscopic cracks and repair these cracks by bonding damaged surfaces. A novel temperature‐responsive SMASH polymer composite was established by introducing Diels–Alder bonds (D–A) in polyurethane. In this article, dynamic D–A produced by the polymerization of furfurylamine and 4,4’‐bismaleimidodiphenylmethane was introduced into the molecular chain to enable the polyurethane elastomers containing D–A bonds to acquire self‐repairing capability. The self‐healing properties of the synthesized material were examined using polarized light microscopy, which revealed excellent fracture healing. The mechanical properties before and after healing were tested, in which the initial maximum tensile strength of the material could reach 7.9 MPa, and the maximum tensile strength after self‐healing was 7.3 MPa, with a repair rate of 91.8%; the maximum elongation was 585.9%, and the maximum elongation after self‐healing was 469.5%, with a repair rate of 80.1%. In addition, this material has excellent repair performance for microcracks of different scales, and the micromolten part of the surface after heating can fill the micrometer cracks, play the role of antiaging, and extend the service life of the material.

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Investigation of Supramolecular Self-Assembly in Sn(IV)-5,10,15,20-tetra(4-bromo-2,6-difluorophenyl) Porphyrins Mediated through Activated Sigma Hole

Bandaru,

Singh,

Titi

et al. 2024

Crystal Growth & Design

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The article presents the design, synthesis, characterization, and investigation of halogen-bonding interactions in a series of six-coordinated Sn(IV) complexes based on 5,10,15,20-tetra(4-bromophenyl) porphyrin [Sn(IV)TBrPr] and 5,10,15,20-tetra(4-bromo-2,6-difluoro phenyl) porphyrin [Sn(IV)TBrFPr] with symmetrical axial linkers 3,5-dibromobenzoic acid (3,5-DiBrBA) and 4-bromobenzoic acid (4-BrBA) and nonsymmetrical axial linker 5-bromo nicotinic acid (5-BrNA). Four compounds, namely, Sn(5-BrNA)2(TBrPr) (1), Sn(5-BrNA)2(TBrFPr)·2DMF (2), Sn(3,5-DiBrBA)2(TBrFPr) (3), Sn(4-BrBA)2(TBrFPr) (4), were synthesized and characterized by single-crystal X-ray crystallography. All of the compounds were characterized by 1H NMR, UV–vis absorption, emission, scanning electron microscopy, and cyclic voltammetry. Diverse supramolecular interactions involving bromine and fluorine atoms like Br···Br, Br···F, Br···π, and F···F are successfully manifested in our systems. The single-crystal analysis reveals that the self-assembly in compound 3 displays the shortest type II Br···Br contact of 3.401(3) Å in the realm of porphyrin assemblies, which leads to the formation of a porphyrin dimer. An interesting example of the shortest Br···F contact of 2.937(2) Å is found in compound 4, which facilitates the formation of 3D supramolecular architecture with well-defined hexagonal voids. The shortest contacts observed in our systems are persuaded by the cooperative interactions of the bromine atoms and by the most electron-withdrawing fluorine atoms on the porphyrin skeleton. Electrostatic potential surface analyses show that the σ-hole potential in the bromine atoms is increased by 6.5 kcal by the fluorine atoms. Optical and electrochemical studies detail the electronic structure of the title compounds under the influence of fluorine atoms and axial linkers, while theoretical studies were conducted to calculate the highest occupied molecular orbital–least unoccupied molecular orbital gap to relate with the experimental values.

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Intermolecular Hydrogen Bonding Directed by Aryl–Perfluoroaryl π–π Stacking Interactions

Cited by 6 publications

References 89 publications

Tailoring the π–π stacking interaction among organic cations in hybrid metal halide crystals towards tunable light emission

Tailoring the π–π stacking interaction among organic cations in hybrid metal halide crystals towards tunable light emission

Synthesis of Diels–Alder bond and hydrogen bond synergistic shape memory self‐healing polyurethane elastomers

Investigation of Supramolecular Self-Assembly in Sn(IV)-5,10,15,20-tetra(4-bromo-2,6-difluorophenyl) Porphyrins Mediated through Activated Sigma Hole

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