Creation of Functional Organic Gels Based on Oligothiophenes

Polymer gels have received a great deal of attention not only from scientific interest but also for their practical applications. Recently, low molecular-weight organic gels have also been receiving growing attention. However, their have been few studies of low molecular-weight organic gels in contrast to extensive studies of polymer gels. In order to develop a novel class of low-molecular-weight organic gels and to gain an insight into the relationship between molecular structures of gel-form…

Creation of Functional Organic Gels Based on Oligothiophenes

Polymer gels have received a great deal of attention not only from scientific interest but also for their practical applications. Recently, low molecular-weight organic gels have also been receiving growing attention. However, their have been few studies of low molecular-weight organic gels in contrast to extensive studies of polymer gels.In order to develop a novel class of low-molecular-weight organic gels and to gain an insight into the relationship between molecular structures of gel-forming compounds and gel-forming properties, a novel family of low molecular-weight organic compounds containing oligothiophene,N,N'-distearyl-5,5"-(2,2':5',2"-terthiophe-ne)dicarboxamide(DNC183T),N,N'-dialkyl-5,5"-(3,3"-dioctyl-2,2':5',2"-terthiophene)dicarboxamide(DNCnDOc3T, n = 5, 8, 16, 18)and N,N'-distearyl-5,5'"-( 3,3'"-dioctyl- 2,2':5',2 ":5",2'"-quaterthiophene)dicarboxamide(DNC1sDOc4T), were designed and synthesized. Whereas DNC183T did not form gels with organic solvents, DNCnDOc3T(n = 8, 16, 18) and DNC18DOc4T were found to form gels with certain organic solvents. These are the first examples of low molecular-weight organic gels containing an oligothiophene moiety. It is of intest to note that while DNC8DOc3T forms opaque gels with alcohols,e.g. ethanol and isopropanol, DNC16DOc3T, DNC18DOc3T and DNC18DOc4Tform transparent gels with hydrocarbon solvents such as heptane, octane, undecane, and others. It is shown that the intermolecular hydrogen bonding and intermolecular interactions between the long alkyl chain in the N-alkylcarboxamide group as well as the incorporation of an alkyl group at the β-position of the thiophene ring play an important role for the formation of gels. The optical micrographs of gels and the SEM images of xerogels showed three-dimensional networks of fibrous bundle structures.DNC18DOc4T gels was found to exhibit a reversible clear color change on electrochemical oxidation and reduction. Thus, low molecular-weight organic gels function as a new type of potential electrochromic materials.