Super organogelator based on tetrathiafulvalene with four amide derivatives and its F4TCNQ charge-transfer complex

Abstract

A new series of tetrathiafulvalene-based organogelators endowed with four hydrophobic chains incorporating amide groups was synthesised and characterised. The resulting transparent organogels were obtained with organic solvents such as cyclohexane, carbon tetrachloride and chlorobenzene. Additionally, the length of the alkyl chain influenced the gelation ability of organogels. Considering the results, we concluded that compounds were ‘super gelators’. Interestingly, the gelators reacted with 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane to form charge-transfer (CT) complexes and binary organogels. 1HNMR and FT-IR revealed that cooperation of hydrogen bonding, π–π and CT interactions was the main driving force for formation of the native and CT gels. The scanning electron microscopy images of native xerogels revealed characteristic gelation morphologies of three-dimensional cross-linking networks, whereas the morphologies of CT complex xerogels showed amorphous rod-like aggregates. X-ray powder diffraction studies suggested that both gelator and CT complex maintained lamellar molecular packing mode in organogel phase.