Crystal Engineering, Electron Conduction, Molecular Recognition and Reactivity by Chalcogen Bonds in Tetracyanoquinodimethanes Fused with [1,2,5]Chalcogenadiazoles

Shimajiri, Takuya; Rouville, Henri‐Pierre Jacquot de; Heitz, Valérie; Akutagawa, Tomoyuki; Fukushima, Takanori; Ishigaki, Yusuke; Suzuki, Takanori

doi:10.1055/a-2072-2951

Cited by 4 publications

(1 citation statement)

References 115 publications

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“…In crystals of the yellow folded form, a sheet-like network is formed through an interheteroatom interaction between S and CN groups − (Scheme b), which is now known as a “chalcogen bond”, − and this facilitates the crystallization of the folded form in the pristine crystal. The observed network is similar to that in the planar tetracyanoquinodimethane derivative 13 fused with two thiadiazole rings exhibiting a two-dimensional network with chalcogen bonds (Scheme c). − On the other hand, the violet twisted form of 12 was isolated as a solvate, in which the chalcogen-bonded network is partially broken, so that it can incorporate solvent molecules.…”

Section: Difference Between the Open-shell Perpendicular Form And The...mentioning

confidence: 99%

Carbon-based Biradicals: Structural and Magnetic Switching

Ishigaki,

Harimoto,

Shimajiri

et al. 2023

Chem. Rev.

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Sterically hindered C�C double bonds often deform into a bent or twisted geometry. Thus, many overcrowded ethylenes or anthraquinodimethanes can adopt multiple conformations, such as a folded form or a twisted form, which are interconvertible under the application of external stimuli. A perpendicular form with biradical character can also be adopted when designed to incorporate a stable carbon-based radical unit, which is involved in stimuliresponsive magnetic switching accompanied by a structural change. This review focuses on recent advances in the development of such strained π-electron systems and reveals the factors that affect the mutual interconversion and switching behavior. The energy barrier for the interconversion of conformational isomers is affected by the tricyclic skeleton or bulky substituents on the C�C double bonds, whereas the relative stability of the perpendicular biradical form increases with the additional insertion of 9,10-anthrylene units into the C�C double bonds. CONTENTS 1. Introduction 13952 2. Difference between the Open-shell Perpendicular Form and the Closed-shell Twisted Form 13953 3. Interconversion between the Biradical Perpendicular Form and Closed-shell Twisted Form of Overcrowded Ethylene 13955 4. Interconversion between the Biradical Perpendicular Form and Closed-shell Folded Form of Anthraquinodimethanes 13956 5. Biradical Perpendicular Form Derived from the Closed-shell Folded Form of Bianthraquinodimethanes 13958 6. Stable Biradical Perpendicular Form with an Oligo(9,10-anthrylene) Unit 13960 7. Biradical Perpendicular Form

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Section: Difference Between the Open-shell Perpendicular Form And The...mentioning

confidence: 99%

Carbon-based Biradicals: Structural and Magnetic Switching

Ishigaki,

Harimoto,

Shimajiri

et al. 2023

Chem. Rev.

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Halide Complexes of 5,6‐Dicyano‐2,1,3‐Benzoselenadiazole with 1 : 4 Stoichiometry: Cooperativity between Chalcogen and Hydrogen Bonding

Radiush,

Wang,

Chulanova

et al. 2023

ChemPlusChem

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The [M4–Hal]– (M = the title compound; Hal = Cl, Br, and I) complexes were isolated in the form of salts of [Et4N]+ cation and characterized by XRD, NMR, UV‐Vis, DFT, QTAIM, EDD, and EDA. Their stoichiometry is caused by a cooperative interplay of σ‐hole‐driven chalcogen (ChB) and hydrogen (HB) bondings. In the crystal, [M4–Hal]– are connected by the π‐hole‐driven ChB; overall, each [Hal]– is six‐coordinated. In the ChB, the electrostatic interaction dominates over orbital and dispersion interactions. In UV‐Vis spectra of the M + [Hal]– solutions, ChB‐typical and [Hal]–‐dependent charge‐transfer bands are present; they reflect orbital interactions and allow identification of the individual [Hal]–. However, the structural situation in the solutions is not entirely clear. Particularly, the UV‐Vis spectra of the solutions are different from the solid‐state spectra of the [Et4N]+[M4–Hal]–; very tentatively, species in the solutions are assigned [M–Hal]–. It is supposed that the formation of the [M4–Hal]– proceeds during the crystallization of the [Et4N]+[M4–Hal]–. Overall, M can be considered as a chromogenic receptor and prototype sensor of [Hal]–. The findings are also useful for crystal engineering and supramolecular chemistry.

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Coordination Polymers between 3,4-Dicyano-1,2,5-telluradiazole and N,N,N′,N′-Tetramethylethane-1,2-diamine: The Decisive Role of Chalcogen Bonding

Pushkarevsky,

Smolentsev,

Wang

et al. 2024

Crystal Growth & Design

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One-dimensional coordination polymers [1•2] ∞ (two polymorphs) and [1 2 •2] ∞ were obtained by cocrystallization of 3,4-dicyano-1,2,5-telluradiazole (1) and N,N,N′,N′-tetramethylethane-1,2-diamine (2). In the presence of Solv (C 6 H 6 , C 5 H 5 N, or C 4 H 4 S), differently colored, depending on the conditions, {[1 2 •2]• Solv} ∞ clathrates were isolated: products synthesized in the light were green, whereas those synthesized in the dark were yellow. In {[1 2 •2]•Solv} ∞ , the Solv molecules occupy cavities formed by methyl groups of 2. With pyridazine, the 1•(1,2-C 4 H 4 N 2 ) 2 discrete complex was synthesized, and no clathrates/complexes were observed with pyrazine (1,4-C 4 H 4 N 2 ) and pyrrole (C 4 H 5 N). In the compounds, 2 connects two 1 or 1 2 by Te•••N chalcogen bonding (ChB), which is decisive for their formation according to quantum theory of atoms in molecules (QTAIM), NBO, and Hirshfeld surface analyses. The ChB features orbital contribution/ polarization. The second-order perturbation energies are structure-dependent, and those for {[1 2 •2]•Solv} ∞ are slightly higher than those for [1•2] ∞ and [1 2 •2] ∞ . Time-dependent density functional theory (TD-DFT) calculations on the X-ray diffraction (XRD) unit cells of green {[1 2 •2]•Solv} ∞ do not reproduce their longest-wavelength absorption, which might indicate minor light-induced side products.

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Crystal Engineering, Electron Conduction, Molecular Recognition and Reactivity by Chalcogen Bonds in Tetracyanoquinodimethanes Fused with [1,2,5]Chalcogenadiazoles

Cited by 4 publications

References 115 publications

Carbon-based Biradicals: Structural and Magnetic Switching

Carbon-based Biradicals: Structural and Magnetic Switching

Halide Complexes of 5,6‐Dicyano‐2,1,3‐Benzoselenadiazole with 1 : 4 Stoichiometry: Cooperativity between Chalcogen and Hydrogen Bonding

Coordination Polymers between 3,4-Dicyano-1,2,5-telluradiazole and N,N,N′,N′-Tetramethylethane-1,2-diamine: The Decisive Role of Chalcogen Bonding

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