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[1,2,5]Thiadiazolo[3,4-<i>d</i>]Pyridazine as an Internal Acceptor in the D-A-π-A Organic Sensitizers for Dye-Sensitized Solar Cells
oleh: Timofey N. Chmovzh, Ekaterina A. Knyazeva, Ellie Tanaka, Vadim V. Popov, Ludmila V. Mikhalchenko, Neil Robertson, Oleg A. Rakitin
Format: | Article |
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Diterbitkan: | MDPI AG 2019-04-01 |
Deskripsi
Four new D-A-π-A metal-free organic sensitizers for dye-sensitized solar cells (DSSCs), with [1,2,5]thiadiazolo[3,4-<i>d</i>]pyridazine as internal acceptor, thiophene unit as π-spacer and cyanoacrylate as anchoring electron acceptor, have been synthesized. The donor moiety was introduced into [1,2,5]thiadiazolo[3,4-<i>d</i>]pyridazine by nucleophilic aromatic substitution and Suzuki cross-coupling reactions, allowing design of D-A-π-A sensitizers with the donor attached to the internal heterocyclic acceptor not only by the carbon atom, as it is in a majority of DSSCs, but by the nitrogen atom also. Although low values of power conversion efficiency (PCE) were found, a few important consequences were identified: (i) poor PCE data can be attributed to high electron deficiency of the internal [1,2,5]thiadiazolo[3,4-<i>d</i>]pyridazine acceptor due to lower light harvesting by the dye; (ii) the manner in which the donor was attached to the internal acceptor (by carbon or nitrogen) did not play an essential role in the photovoltaic properties of the dyes; (iii) dyes based on the novel donor 2,3,4,4a,9,9a-hexahydro-1<i>H</i>-1,4-methanocarbazolyl and 9-(<i>p</i>-tolyl)-2,3,4,4a,9,9a-hexahydro-1<i>H</i>- carbazole moieties showed similar photovoltaic properties to dyes based on the well-known 4-(<i>p</i>-tolyl)-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indolyl building block, which opens the door for further optimization potential of new dye families.