Chalcogen Bond versus Weak Hydrogen Bond: Changing Contributions in Determining the Crystal Packing of [1,2,5]-Chalcogenadiazole-Fused Tetracyanonaphthoquinodimethanes

Ishigaki, Yusuke; Asai, Kota; Shimajiri, Takuya; Akutagawa, Tomoyuki; Fukushima, Takanori; Suzuki, Takanori

doi:10.1055/s-0041-1725046

Cited by 6 publications

(2 citation statements)

References 6 publications

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“…44–49 The E–X chalcogen bondings are also observed for X atoms belonging to ring substituents and competing with the chalcogenadiazoles’ N atoms for the σ -holes. 50,51 Notably, the [E–N] 2 -bonded dimers may exist not only in the solid state, but in the gas phase as well. 52…”

Section: Introductionmentioning

confidence: 99%

Chalcogen-bonded donor–acceptor complexes of 5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazine with halide ions

et al. 2022

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Section: Introductionmentioning

confidence: 99%

Chalcogen-bonded donor–acceptor complexes of 5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazine with halide ions

et al. 2022

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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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Solid‐State Assembly by Chelating Chalcogen Bonding in Quinodimethane Tetraesters Fused with a Chalcogenadiazole

et al. 2022

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In contrast to p-quinodimethane tetraesters, which undergo facile polymerization due to their diradical character, newly synthesized 1 and 2 consisting of a chalcogenadiazole fused to a p-naphthoquinodimethane tetraester are thermodynamically stable due to butterfly-shaped deformation. Such a folded molecular structure is also favorable for chalcogen bond (ChB) formation through intermolecular close contacts between a chalcogen atom (E: Se or S) and the oxygen atoms of ester groups in a crystal. The less-explored chelating-ChB through a C=Ois the key supramolecular synthon for the formation of a one-dimensional rod-like assembly in a crystal, which is commonly observed in selenadiazole-tetraesters (1) with OMe, OEt, and OiPr groups. The formation of inclusion cavities between the rods shows that 1 could serve as solid-state host molecules for clathrate formation, as found in a hexane-solvated crystal. In contrast, thiadiazole-tetraesters (2) are less suitable for the formation of a rod-like assembly since the ChB involving S is less effective, and thus is overwhelmed by weak hydrogen bonds through CÀ H•••O contacts.

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Chalcogen Bond versus Weak Hydrogen Bond: Changing Contributions in Determining the Crystal Packing of [1,2,5]-Chalcogenadiazole-Fused Tetracyanonaphthoquinodimethanes

Cited by 6 publications

References 6 publications

Chalcogen-bonded donor–acceptor complexes of 5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazine with halide ions

Chalcogen-bonded donor–acceptor complexes of 5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazine with halide ions

Carbon-based Biradicals: Structural and Magnetic Switching

Solid‐State Assembly by Chelating Chalcogen Bonding in Quinodimethane Tetraesters Fused with a Chalcogenadiazole

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