9-(p-Tolyl)-2,3,4,4a,9,9a-hexahydro-1H-carbazole—A new donor building-block in the design of sensitizers for dye-sensitized solar cells

Abstract The novel donor building-block - 9-(p-tolyl)-2,3,4,4a,9,9a-hexahydro-1H-carbazole was designed and employed in the synthesis of dye-sensitized solar cell (DSSCs). An effective, high-yielding synthesis of 4,6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-(p-tolyl)-1,2,3,4,4a,9a-hexahydrocarbazole from 1,2,3,4,4a,9a-hexahydrocarbazole was realized. Three new metal-free organic sensitizers, containing the new donor building block were prepared by a stepwise approach from 4,7-dibromobenzo[c][1,2,5]chacogenadiazoles. A 2,1,3-Benzothiadiazole dye containing hexahydrocarbazole donor, thiophene as π-spacer and cyanoacrylate as anchoring electron acceptor showed photovoltaic properties higher than the well-known WS-2 sensitizer with PCE = 5.86 %. Although benzoxa- and –selenadiazole dyes have a bathochromic shift (24−30 nm) in the UV–vis spectra, and smaller energy gap Eg (about 0.1 eV), they have lower photovoltaic parameters, including PCE of 1.5–2.3 %. Introducing a new donor 9-(p-tolyl)-2,3,4,4a,9,9a-hexahydro-1H-carbazole into the construction of the DSSCs has broadened possibilities for the optimization of their photovoltaic properties.