Supramolecular gels based on monopyrrolotetrathiafulvalene and its TCNQ charge-transfer complex

Abstract

A novel series of monopyrrolotetrathiafulvalene (monopyrrolo-TTF)-based low molecular-mass organic gelators (LMOGs) were synthesized and characterized. Electrochemical investigations exhibited two reversible one-electron redox couples. The gelators could gelate some saturated hydrocarbons and alcohols. The FE-SEM images of xerogels revealed the characteristic gelation morphologies of microporous structures. The gelators reacted with tetracyano-p-quinodimethane (TCNQ) to form the charge-transfer (CT) complexes and the binary organogels, and the morphologies of binary gels changed to regular network and fiber in cyclohexane and n-hexane, respectively. XRD studies suggest that both the gelator and the CT complex maintain the lamellar molecular-packing mode in the organogel phase. The gel–sol transition of the organogel and the CT complex gel could be stimulated by fluorine and chlorine ions.