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Exploring Structure-Property Relationships in a Bio-Inspired Family of Bipodal and Electronically-Coupled Bistriphenylamine Dyes for Dye-Sensitized Solar Cell Applications
Open AccessArticle

Synthesis of Novel 3,6-Dithienyl Diketopyrrolopyrrole Dyes by Direct C-H Arylation

Department of Chemistry, Norwegian University of Science and Technology (NTNU), N-7491 Trondheim, Norway
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Molecules 2020, 25(10), 2349; https://doi.org/10.3390/molecules25102349
Received: 24 April 2020 / Revised: 13 May 2020 / Accepted: 15 May 2020 / Published: 18 May 2020
(This article belongs to the Special Issue Recent Advances in Dye-Sensitized Solar Cells)
Direct C-H arylation coupling is potentially a more economical and sustainable process than conventional cross-coupling. However, this method has found limited application in the synthesis of organic dyes for dye-sensitized solar cells. Although direct C-H arylation is not an universal solution to any cross-coupling reactions, it efficiently complements conventional sp2−sp2 bond formation and can provide shorter and more efficient routes to diketopyrrolopyrrole dyes. Here, we have applied palladium catalyzed direct C-H arylation in the synthesis of five new 3,6-dithienyl diketopyrrolopyrrole dyes. All prepared sensitizers display broad absorption from 350 nm up to 800 nm with high molar extinction coefficients. The dye-sensitized solar cells based on these dyes exhibit a power conversion efficiency in the range of 2.9 to 3.4%. View Full-Text
Keywords: direct C-H arylation; dye-sensitized solar cells; diketopyrrolopyrrole; phenothiazine; triarylamine; dye direct C-H arylation; dye-sensitized solar cells; diketopyrrolopyrrole; phenothiazine; triarylamine; dye
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Yemene, A.E.; Venkatraman, V.; Moe Almenningen, D.; Hoff, B.H.; Gautun, O.R. Synthesis of Novel 3,6-Dithienyl Diketopyrrolopyrrole Dyes by Direct C-H Arylation. Molecules 2020, 25, 2349.

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