Catalytic C–H Arylation of Tetrathiafulvalenes for the Synthesis of Functional Materials

Abstract

Sulfur-containing functional π-conjugated cores play key roles in materials science, mostly due to their unique electrochemical and photophysical properties. Among these, the excellent electron donor tetrathiafulvalene (TTF) has occupied a central position since the emergence of organic electronics. Peripheral C–H modification of this highly useful sulfur-containing motif has resulted in the efficient creation of new molecules that expand the applications of TTFs. This Short Review begins with the development of the palladium-catalyzed direct C–H arylation of TTF. Subsequently, it summarizes the applications of this efficient C–H transformation for the straightforward synthesis of useful TTF derivatives that are employed in a variety of research fields, demonstrating that the development of a new reaction can have a significant impact on chemical science.

1 Introduction

2 Development of the Palladium-Catalyzed Direct C–H Arylation of TTF

3 Synthesis of TTF-Based Tetrabenzoic Acid and Tetrapyridine for MOFs

4 Synthesis of TTF-Based Tetrabenzaldehyde and Tetraaniline for COFs

5 Tetraarylation of TTFAQ

6 Synthesis of Multistage-Redox TTF Derivatives

7 Miscellaneous Examples

8 Conclusions

Key words

C–H arylation - tetrathiafulvalene - sulfur - palladium catalysis - metal-organic framework - covalent organic framework - supramolecular chemistry - redox-active material

Publication History

Received: 19 June 2020

Accepted after revision: 16 July 2020

Article published online:
08 September 2020

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