A novel family of low molecular-weight organic gels.: 1,3,5-tris(N-phenyl-N-4-stearoylaminophenylamino)benzene and 4,4′,4"-tris(N-phenyl-N-4-stearoylaminophenylamino)triphenylamine/organic solvent systems

For the purpose of developing a novel family of low molecular-weight organic gels and examining the relationship between molecular structures of gel-forming compounds and morphologies of resulting gels, novel low molecular-weight organic compounds, 1,3,5-tris(N-phenyl-N-4-stearoylaminophenylamino)benzene (TSA-TDAB) and 4,4',4 "-tris(N-phenyl-N-4-stearoylaminophenylamino)triphenylamine (TSA-TDATA), were designed and synthesized. Both TSA-TDAB and TSA-TDATA were found to form thermoreversible gels with a variety of organic solvents at low concentrations below 10 wt%. Comparison of the infrared absorption spectra between the gels and the corresponding solutions of TSA-TDAB and TSA-TDATA showed that the intermolecular hydrogen bonding plays an important role for gel formation. The morphologies of the xerogels of TSA-TDAB and TSA-TDATA were dependent upon the solvent. Fibrous three-dimensional networks were observed for the xerogels of both compounds except for the xerogels obtained from TSA-TDAB/nonpolar solvent gels. A TSA-TDATA/benzonitrile gel containing tetra-n-butylammonium perchlorate was found to function as a new type of electrochromic material, exhibiting a reversible color change on electrochemical oxidation and reduction.