Synthesis and properties of tetrathiafulvalenes bearing 6-aryl-1,4-dithiafulvenes.

Beilstein Journal of Organic Chemistry
Aya YoshimuraYohji Misaki

Abstract

Novel multistage redox tetrathiafulvalenes (TTFs) bearing 6-aryl-1,4-dithiafulvene moieties were synthesized by palladium-catalyzed direct C-H arylation. In the presence of a catalytic amount of Pd(OAc)2, P(t-Bu3)·HBF4, and an excess of Cs2CO3, the C-H arylation of TTF with several aryl bromides bearing 1,3-dithiol-2-ylidenes took place efficiently to produce the corresponding π-conjugated molecules. We also succeeded in the estimation of the oxidation potentials and number of electrons involved in each oxidation step of the obtained compounds by digital simulations.

References

Apr 24, 2001·Angewandte Chemie·José L. Segura, Nazario Martín
Nov 10, 2001·The Journal of Organic Chemistry·R R AmareshL D Kispert
Jul 19, 2002·Organic Letters·Desikan RajagopalMichael P Cava
Nov 13, 2004·Chemical Reviews·Masahiko IyodaYoshihiro Miyake
Dec 15, 2006·Chemical Reviews·Mojtaba Gholami, Rik R Tykwinski
Apr 21, 2009·Chemical Communications : Chem Comm·David CanevetDaoben Zhu
Jul 6, 2009·Science and Technology of Advanced Materials·Yohji Misaki

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Citations

Jun 5, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Aya Yoshimura, Yohji Misaki

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Methods Mentioned

BETA
NMR

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