N-Alkyl- and N-aryl-dithieno[3,2-b:2′,3′-d]pyrrole-containing organic dyes for efficient dye-sensitized solar cells

Two new organic sensitizers, 2-cyano-3-(6-(4-(diphenylamino)phenyl)-4-(2-ethylhexyl)-4H-dithieno[3,2-b:2′,3′-d]pyrrol-2-yl)acrylic acid and 2-cyano-3-(6-(4-(diphenylamino)phenyl)-4-(4-(hexyloxy)phenyl)-4H-dithieno[3,2-b:2′,3′-d]pyrrol-2-yl)acrylic acid, consisting of electron donating (triphenylamin...

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Bibliographic Details
Published in:Tetrahedron 2014-03, Vol.70 (12), p.2141-2150
Main Authors: Gupta, Akhil, Kelson, Melissa M.A., Armel, Vanessa, Bilic, Ante, Bhosale, Sheshanath V.
Format: Article
Language:English
Subjects:
Analogue
Charge transfer
Condensing
Dithienopyrrole
Donor–π-acceptor
Dye-sensitized solar cells
Dyes
Electrolytes
Knoevenagel condensation
Photovoltaic cells
Solar cells
Tetrahedrons
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Summary:Two new organic sensitizers, 2-cyano-3-(6-(4-(diphenylamino)phenyl)-4-(2-ethylhexyl)-4H-dithieno[3,2-b:2′,3′-d]pyrrol-2-yl)acrylic acid and 2-cyano-3-(6-(4-(diphenylamino)phenyl)-4-(4-(hexyloxy)phenyl)-4H-dithieno[3,2-b:2′,3′-d]pyrrol-2-yl)acrylic acid, consisting of electron donating (triphenylamine) and electron accepting (cyanoacrylic acid) functionalities linked by two different rigidified π-spacers, N-alkyl- and N-aryl-dithieno[3,2-b:2′,3′-d]pyrrole, were designed, synthesized and applied for dye-sensitized solar cells, respectively. The materials were successfully synthesized through Knoevenagel condensation reactions. Ultraviolet–visible absorption spectra revealed that the use of either of rigidified π-spacer resulted in similar charge transfer transition, however, enhanced spectral response was observed when compared with an oligothiophene analogue. In terms of their photovoltaic performance, new dyes outperformed the reference bithiophene sensitizer when tested with nitrile-based and ionic liquid-based electrolytes. [Display omitted] Two new organic sensitizers, 1 and 2, consisting of an electron donating (triphenylamine) and an electron accepting (cyanoacrylic acid) functionality linked by two different rigidified π-spacers were applied for dye-sensitized solar cells. UV–Vis absorption spectra of 1 and 2 revealed enhanced spectral response when compared with an oligothiophene analogue, and they yielded 6.1% and 6.2% power conversion efficiencies, respectively.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.02.002