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

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 Full article

Journal

Journal of Photochemistry and Photobiology A: Chemistry
ISSN: 1010-6030 , E-ISSN: 1873-2666

Output data

Year: 2020, Volume: 391, Article number : 112333, Pages count : DOI: 10.1016/j.jphotochem.2019.112333

Authors

Mikhailov Maxim S. ¹ , Gudim Nikita S. ² , Knyazeva Ekaterina A. ^2,1 , Tanaka Ellie ³ , Zhang Lu ³ , Mikhalchenko Ludmila V. ² , Robertson Neil ³ , Rakitin Oleg A. ^2,1

Affiliations

1	Nanotechnology Education and Research Center, South Ural State University, 454080, Chelyabinsk, Russia
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Moscow, Russia
3	EaStCHEM School of Chemistry, University of Edinburgh, Edinburgh, EH9 3FJ, UK

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.

Mikhailov M.S. , Gudim N.S. , Knyazeva E.A. , Tanaka E. , Zhang L. , Mikhalchenko L.V. , Robertson N. , Rakitin O.A.
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
Journal of Photochemistry and Photobiology A: Chemistry. 2020. V.391. 112333 . DOI: 10.1016/j.jphotochem.2019.112333 WOS Scopus OpenAlex

Web of science:	WOS:000514008000018
Scopus:	2-s2.0-85078077021
OpenAlex:	W2996697269

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OpenAlex	33
Scopus	33
Web of science	32