Synthesis And Gelation Property Of Organic Gelators Basedonmonopyrro-Tetrathiafulvalene

Low molecular-mass organic gelators (LMOGs) have generated considerable interest during the past decade for the design of smart materials. Because they are capable of creating a supramolecular structure with the ability to immobilize organic media through noncovalent intermolecular interactions, such as hydrogen bonding, π-π stacking, van der Waals, electrostatic interactions, and so forth. Significant research interest has been dedicated towards functional organic materials consisting of π-conjugated molecular building blocks due to their potential applications inorganic electronics and photonics. In recent years, self-assembly of TTF derivatives through intermolecular interaction leads to gelation of some organic solvents and have been widely investigated for organic conducting materials.We designed and synthesized a novel series of monopyrrolotetrathiafulvalene (monopyrrolo-TTF)-based low molecular-mass organic gelators (LMOGs). Their molecular structures are characterized by1H-NMR13C-NMR, FT-IR and MALDI-TOF-MS.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 CT complex maintain the lamellar molecular-packing mode in the organogel phase. The gel-sol transition of the organogel and CT complex gel could be stimulated by fluorine and chlorine ions.