Reakcje cykloaddycji alkinów do [beta]-ketoestrów - nowe możliwości w syntezie prekursorów polimerów przewodzących

Abstract

Dissertation takes the issue to synthesis o f conductive po lymer precu rsors which are thiophene derivalives and their properties - primarily electrochemistry and spectroclcctrochcmistry. Comprehensive electrochemical and spectroelectrochemical studies, as we 11 as knowledge gained in DFT calculations allow for a detailed discussion o f the construction o f the resulting compounds and their properties. The first stage o f doctoral thesis was to dcvc!op methods o f obtaining, separation, and vcrification the structure o f compounds (precursors) to belong to group (tetra-, penta- or hexasubstituted) benzene derivatives and (tri- or tetrasubstituted) 2-pyranone derivatives. Schedulcd molecules were synthesized by ([2+2+2] or [2+1+2+1]) cycloaddition reaciions o f alkynes to p-keto esters and [4+2] Diels-AIdcr cycloaddition. The preparation o f the finał products was preceded by the synthesis o f the necessary substrates, exactly alkynes (obtained by Sonogashira coupling) as well as [3-kcto esters. Construction o f the synthesized compounds was verified by 11I, ljC NMR spectroscopy and HRMS. For compounds obtained as solids. the melting points were measured. In the second stage o f doctoral thesis, the synthesized compounds were investigation to electrochemical methods by cyclic voltammetrv (CV) and differential pulse voltammetry (DPV). For all the precursors (monomers), polymerization tests were carried out to obtain the polymers. The polymers were subjected to spectroelectrochemistry studies. The above mentioned studies have allowed us to determine in what conditions can be used from the designed precursors (monomers) to obtain conductive polymers and to determine the basie properties o f the materials, which determine their practical applications.