Calix[4]arenes with 1,2- and 1,3-upper rim tetrathiafulvalene bridges.

Herein we report the synthesis of several calix[4]arene derivatives with tetrathiafulvalene bridges at the upper rim. Calix[4]arene-tetrathiafulvalene (TTF) conjugates4a–d, fixed inconeconformation and comprising two smaller 1,2-bridges, were prepared by cyclisation of tetrakis-chloromethylated calix[4]arene1with 2,3-dithiolates of TTFs. Larger calix[4]arene-TTF macrocycles14and15, also inconeconformation, contain 1,3-bridges and were synthesised by cyclisation of 2,6- and 2,7-dithiolates of TTFs with bis-bromomethylated calix[4]arene7. Redox properties of new calix[4]arene-TTF conjugates were characterised using cyclic voltammetry. [ABSTRACT FROM AUTHOR]