A homologous series of mixed oligoheterocycles 2 ± 6, based on the end-capped quinquethiophene EC5T 1, was synthesized by the introduction of electronegative heteroatoms, such as oxygen and nitrogen, into the conjugated p-system. This led to novel structures in which the central thiophene unit of the parent compound 1 is substituted by other heterocycles (thiazole, 1,3,4-thiadiazole, furan, oxazole, 1,3,4-oxadiazole) that have a more pronounced acceptor character. The characterization of the optical and electrochemical properties clearly reveal the influence of the heteroatoms on the electronic properties. The electron-withdrawing character of the central heterocycles renders the oxidation of the oligomer more difficult while reduction is facilitated. Moreover, in some cases a hypsochromic shift of the longest-wavelength absorption and emission is observed along with a significant enhancement of the fluorescence quantum yield in solution and in the solid state. The HOMO/LUMO energy difference, determined from optical and electrochemical measurements, corresponds qualitatively well with the values obtained from semiempirical calculations. An X-ray structural determination was performed on oligoheterocycle 6 and the experimental and calculated data are compared.
A novel covalently linked donor-acceptor dyad comprising a dithienopyrrol-based oligomeric donor and a fullerene acceptor was synthesized and characterized. The concomitant effect of favorable optoelectronic properties, energy levels of the frontier orbitals, and ambipolar charge transport enabled the application of the dyad in simplified solution-processed single material organic solar cells reaching a power conversion efficiency of 3.4%.<br><br><br>
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A novel covalently linked donor-acceptor dyad comprising a dithienopyrrol-based oligomeric donor and a fullerene acceptor was synthesized and characterized. The concomitant effect of favorable optoelectronic properties, energy levels of the frontier orbitals, and ambipolar charge transport enabled the application of the dyad in simplified solution-processed single material organic solar cells reaching a power conversion efficiency of 3.4%.<br><br><br>
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