Synthesis of fully functionalized furan main chain polyester through multi component reactions

Chemical reactions that possess properties such as high efficiency, atom-economy, modularity and ease of execution/purification are very much looked after in polymer chemistry and many other research areas like life and material sciences, organic chemistry and chemical biology. A reaction category with such attributes is the "click reaction", first described by K. B. Sharpless and colleagues in 2001. In parallel to the progress based on "click" reactions in organic chemistry area, many notable applications to polymer chemistry such as copper-catalyzed azide–alkyne cycloaddition (CuAAC), thiol– ene/yne free-radical addition and the (hetero) Diels–Alder reaction were introduced. Multicomponent reactions (MCRs) is another example of such sought after chemical reactions, as they offer an elegant way of producing highly selective products in which majority of the atoms of the starting materials (more than two) are present. Interestingly, MCRs made their debut in the area of polymer chemistry only recently although their unique properties are acknowledged since more than 150 years from today. For instance, Passerini, Ugi and Kabachnik-Fields are notable examples of MCRs that are widely utilized in the area of polymer chemistry. Another popular application in the organic chemistry research area is the synthesis of heterocyclic compounds such as furans and pyrroles via MCRs. We have developed the idea of bringing together the applications of MCRs in organic chemistry to synthesize heterocyclic compounds and their use in polymer chemistry. In the context of current MCR literature, we have identified that utilizing MCRs to prepare polymers with fully functionalized heterocyclic main and/or side chains as an exciting and so far unexplored application of MCRs. Therefore, the objective in this thesis is to employ MCRs for the first time in the preparation of fully functional furan main chain polyesters. Initially, the polyester having an electron deficient alkyne function on the main chain was prepared and later reacted with cyclohexyl isocyanide and benzaldehyde in various MCR conditions. The impact of temperature, duration, aldehyde equivalents with respect to isocyanide and the alkyne components on the MCR were studied. The furan main chain polyester was characterized by GPC and its structure was confirmed by both 1H and 13C NMR spectra. MCR efficiencies were calculated by the use of 1H NMR spectra.