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

Maxim S. Mikhailov, Nikita S. Gudim, Ekaterina A. Knyazeva, Ellie Tanaka, Lu Zhang, Ludmila V. Mikhalchenko, Neil Robertson, Oleg A. Rakitin

Research output: Contribution to journalArticlepeer-review

Abstract / Description of output

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.
Original languageEnglish
Pages (from-to)112333
JournalJournal of Photochemistry and Photobiology A: Chemistry
Early online date19 Dec 2019
Publication statusPublished - 15 Mar 2020


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