Synthesis and electronic tuning of a diverse family of thiophene derivatives

Easy access to small molecules with interesting photophysical and electrochemical properties is desired by both academia and industry. One way to access these molecules is by the incorporation of a core with functionality that allows for easy derivatization. The Hinsberg thiophene ring synthesis was implemented as the route of choice for the synthesis of 19 thiophene derivatives. These derivatives range from simple organic acids to complex fused aromatic systems. A variety of electronic donors and electronic acceptors have been studied, as has the effect of extended pi-conjugation. Photon absorption ranges from 300 nm to 700 nm and molar absorptivities as high as 60000 M -1cm-1corresponding to HOMO-LUMO energy differences as low as 1.9 eV. Compounds were characterized using a variety of analytical techniques including; UV-Vis, IR, cyclic voltammetry, NMR and fluorescence.