[1,2,5]Thiadiazolo[3,4-d]Pyridazine as an Internal Acceptor in the D-A-π-A Organic Sensitizers for Dye-Sensitized Solar Cells

[1,2,5]Thiadiazolo[3,4-d]Pyridazine as an Internal Acceptor in the D-A-π-A Organic Sensitizers for Dye-Sensitized Solar Cells Full article

Journal

Molecules
ISSN: 1420-3049

Output data

Year: 2019, Volume: 24, Number: 8, Article number : 1588, Pages count : DOI: 10.3390/molecules24081588

Authors

Chmovzh Timofey N ¹ , Knyazeva Ekaterina A ^1,2 , Tanaka Ellie ³ , Popov Vadim V ² , Mikhalchenko Ludmila V ¹ , Robertson Neil ³ , Rakitin Oleg A ^1,2

Affiliations

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

Four new D-A-π-A metal-free organic sensitizers for dye-sensitized solar cells (DSSCs), with [1,2,5]thiadiazolo[3,4-d]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-d]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-d]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-1H-1,4-methanocarbazolyl and 9-(p-tolyl)-2,3,4,4a,9,9a-hexahydro-1H- carbazole moieties showed similar photovoltaic properties to dyes based on the well-known 4-(p-tolyl)-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indolyl building block, which opens the door for further optimization potential of new dye families.

Chmovzh T.N. , Knyazeva E.A. , Tanaka E. , Popov V.V. , Mikhalchenko L.V. , Robertson N. , Rakitin O.A.
[1,2,5]Thiadiazolo[3,4-d]Pyridazine as an Internal Acceptor in the D-A-π-A Organic Sensitizers for Dye-Sensitized Solar Cells
Molecules. 2019. V.24. N8. 1588 . DOI: 10.3390/molecules24081588 WOS Scopus OpenAlex

Web of science:	WOS:000467765700143
Scopus:	2-s2.0-85064845499
OpenAlex:	W2937416497

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OpenAlex	30
Scopus	29
Web of science	25