Exo-Methylene-BEDT-TTF and alkene-functionalised BEDT-TTF derivatives: synthesis and radical cation salts

Matteo Zecchini,Lee Martin,Scott W Allen,Simon J Coles,John D Wallis,Claire Wilson,Hiroki Akutsu,Jordan R Lopez

doi:10.1039/c5ra03921e

Abstract

The syntheses of novel BEDT-TTF donors with either an exo-alkene group or a terminal alkene side chain are described along with the crystal structures of their first radical cation salts which include a new semiconductor.

Highlights

Organosulfur donors such as TTF 1 and BEDT-TTF 2 have been used as substrates for preparation of conducting materials by oxidation either by electrocrystallisation or treatment with electron-de cient acceptor substances, leading to conducting, semi-conducting and in some cases, superconducting materials.[1]
There are a few reports of the BEDT-TTF derivative 6 where just one dithiin ring contains an extra double bond,[6,7] and some of its monosubstituted derivatives such as the methyl derivative 7.6,8 The inclusion of one or two extra double bonds raises the oxidation potential from that of BEDT-TTF by 0.06 and 0.14 V respectively.[6]
We report the preparation of three new donors 8–10, one with an exocyclic double bond attached to the BEDT-TTF framework and a tautomer of 7, and two with an alkene group at the end of a side chain

Summary

Introduction

Organosulfur donors such as TTF 1 and BEDT-TTF 2 have been used as substrates for preparation of conducting materials by oxidation either by electrocrystallisation or treatment with electron-de cient acceptor substances, leading to conducting, semi-conducting and in some cases, superconducting materials.[1]. We report the preparation of three new donors 8–10, one with an exocyclic double bond attached to the BEDT-TTF framework and a tautomer of 7, and two with an alkene group at the end of a side chain

Discussion

Conclusion

TTF Chemistry