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

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

doi:10.1055/a-2072-2951

Synlett, Inhaltsverzeichnis

Synlett 2023; 34(17): 1978-1990
DOI: 10.1055/a-2072-2951

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

Takuya Shimajiri

^aDepartment of Chemistry, Faculty of Science, Hokkaido University, Sapporo, Hokkaido 060-0810, Japan

^bCreative Research Institution, Hokkaido University, Sapporo, Hokkaido 001-0021, Japan

,

Henri-Pierre Jacquot de Rouville

^cLaboratoire de Synthèse des Assemblages Moléculaires Multifonctionnels, Institut de Chimie de Strasbourg, CNRS UMR 7177, Université de Strasbourg, 4, rue Blaise Pascal, 67000 Strasbourg, France

,

Valérie Heitz

^cLaboratoire de Synthèse des Assemblages Moléculaires Multifonctionnels, Institut de Chimie de Strasbourg, CNRS UMR 7177, Université de Strasbourg, 4, rue Blaise Pascal, 67000 Strasbourg, France

,

Tomoyuki Akutagawa

^dInstitute of Multidisciplinary Research for Advanced Materials, Tohoku University, Sendai, Miyagi 980-8577, Japan

,

Takanori Fukushima

^eLaboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, Yokohama 226-8503, Japan

,

Yusuke Ishigaki

^aDepartment of Chemistry, Faculty of Science, Hokkaido University, Sapporo, Hokkaido 060-0810, Japan

,

Takanori Suzuki ∗

^aDepartment of Chemistry, Faculty of Science, Hokkaido University, Sapporo, Hokkaido 060-0810, Japan

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Abstract

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Abstract

Studies on a series of tetracyanoquinodimethanes (TCNQs) fused with [1,2,5]chalcogenadiazole rings reveals that chalcogen bonds (ChBs), through E•••N≡C (E = S or Se) contacts, are a decisive factor in determining their crystal structures, with the formation of one- or two-dimensional networks in a lateral direction. For anion-radical salts generated by one-electron reduction, electron conduction occurs in the direction of the network due to intermolecular electronic interactions involving ChBs. Based on the reliable synthon E•••N≡C for crystal engineering, molecular recognition occurs so that solid-state molecular complexes are selectively formed with certain donors, such as xylenes, among their isomers by charge-transfer-type clathrate formation. The inclusion cavity of the clathrate might provide a reaction environment for photoinduced electron transfer in the solid state. The accommodation of multiple conformers of overcrowded ethylene exhibiting thermo/mechanochromism is another example of a novel function that can be realized by ChBs through E•••N≡C contacts. Therefore, these chalcogenadiazolo-TCNQs endowed with the ability to form ChBs are promising materials for the development of novel solid-state functions.

1 Introduction

2 Bis[1,2,5]thiadiazolo-TCNQ (BTDA)

2.1 Chalcogen Bonds in Crystal Structures of BTDA and its Se Analogues

2.2 Electronic Effects of Chalcogen Bonds in Organic Conductors Consisting of BTDA

2.3 Molecular Recognition by Chalcogen Bonds in Molecular Complexes of BTDA

2.4 Single-Crystalline-State Photoreactions of Molecular Complexes of BTDA

2.5 Overcrowded Ethylene Composed of a BTDA Substructure

3 TCNQ Analogues Fused with a [1,2,5]Chalcogenadiazole

3.1 Crystal Structures of Chalcogenadiazolo-TCNQs

3.2 Crystal Structures of Chalcogenadiazolo-TCNNQs: An E•••N≡C Chalcogen Bond versus a Weak C–H•••N≡C Hydrogen Bond

3.3 Molecular Recognition by Chalcogen Bonds in TCNNQ Derivatives

4 Outlook

Key words

supramolecular chemistry - host–guest systems - heterocycles - electron transfer - chalcogen bond - charge-transfer complex - overcrowded ethylene - crystal structure

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