New chromophores based on combination of ethylenedioxythiophene and carbazole fragments: synthesis and optoelectronic properties

Two new D-π-A chromophores composed of an electron-donating carbazole unit linked through π- bridges, bearing 3,4-ethylenedioxythiophene (EDOT) moiety, with an electron withdrawing dicyanovinyl group (DCV) were successfully synthesized involving Suzuki or Heck cross-coupling and Knöevenagel reactions as the key steps. The obtained compounds absorb light over a broad spectral range, including the visible spectrum. The HOMO/LUMO energies and band gap energy values (Eg) were calculated on the basis of the experimental optical and electrochemical data: HOMO, LUMO, Eg (eV), −5.51, −3.14, 2.37 (4), −5.34, −3.14, 2.20 (7). The presence of the HC=CH unit in compound 7 resulted in the increase of the HOMO energy level, the decrease of a band gap value and red shifts of the absorption and emission bands in comparison with those of 4. Large Stokes shifts and broadband luminescence inherent to both chromophores suggest their use as materials for luminescent solar collectors (LSCs). The obtained compounds demonstrated good solubility and suitable thin-film forming properties. For this reason, they may be suitable for solution-processable photovoltaic applications