108666-51-9

Upstream product

• 31366-25-3 tetrathiafulvalene 
• 882-33-7 diphenyldisulfane 
• 1449506-83-5 C₁₅H₁₀OS₄ 
• 120397-77-5 4,5-bis(phenylthio)-1,3-dithiole-2-thione 
• 591-50-4 iodobenzene 

Relevant academic research and scientific papers

Molecular and crystal structure diversity, and physical properties of tetrathiafulvalene derivatives substituted with various aryl groups through sulfur bridges

A library of tetrathiafulvalene (TTF) derivatives (TTF-1-TTF-47) bearing aryl groups attached through sulfur bridges has been created. The peripheral aryl groups exert a significant influence on both the electronic and crystallographic properties of the resulting TTFs. These TTFs display broad absorption bands at 400-500 nm caused by intramolecular charge-transfer transitions between the aryl groups and central TTF core, and their first redox potentials increase with increasing electron-withdrawing ability of the aryl groups. In their crystal structures (22 examples), the central TTF cores adopt various conformations, including chair, half-chair, boat, and planar conformations. Moreover, the peripheral aryl groups exhibit multiple alignment modes with respect to the central TTF core, caused by their rotation about the two C-S bonds of the sulfur bridges. The packing motifs of these TTFs depend on both the nature of the aryl groups and their spatial alignment modes. Driven by intermolecular van der Waals forces and π-π interactions between the aryl groups and between the aryl groups and the TTF core, these TTFs adopt various packing structures. As a typical example, TTF-14, an achiral molecule, adopts a helical chain stack through intermolecular atomic close contacts. Moreover, the molecular geometries and packing motifs of these TTFs are sensitive to environmental variation, as exemplified by TTF-28, which adopts three distinct crystal modifications with diverse molecular geometries and stacking modes under different crystallization conditions. This work indicates that these TTFs are potential candidates as electronic materials, as well as functional building blocks for supramolecular assembly. Structural diversity due to flexible linkers: A thorough investigation of the properties and structural diversity of tetrathiafulvalene (TTF) derivatives substituted with various aryl groups through sulfur bridges is reported (see graphic). The aryl groups significantly affect both the electronic and crystallographic properties of the TTFs. These TTFs are candidates as electronic materials, as well as functional building blocks for supramolecular assembly. Copyright

Straightforward access to aryl-substituted/fused 1,3-dithiole-2- chalcogenones by Cu-catalyzed C-S coupling between aryl iodides and zinc-thiolate complex (TBA)2[Zn(DMIT)2]

The Cu-catalyzed C-S coupling between iodoaryl and a zinc-thiolate complex was achieved. This protocol provides a facile and efficient synthetic approach for aryl-substituted/fused 1,3-dithiole-2-chalcogenones, which can be converted to TTFs. The Royal Society of Chemistry 2013.