Cross-Dehydrogenative Coupling (CDC) as Key-Transformations to Various D−π–A Organic Dyes: C–H/C–H Synthetic Study Directed toward Dye-Sensitized Solar Cells Applications

Cross-Dehydrogenative Coupling (CDC) as Key-Transformations to Various D−π–A Organic Dyes: C–H/C–H Synthetic Study Directed toward Dye-Sensitized Solar Cells Applications

A variety of push–pull type organic dyes are facilely synthesized through the most atom-economical C–H/C–H dehydrogenative coupling reactions. After comprehensive synthetic optimizations, a broad substrate scope is achieved and functional groups, such as ester, ketone, nitrile, nitro, and triazene a...

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Veröffentlicht in:Journal of organic chemistry 2017-04, Vol.82 (7), p.3538-3551
Hauptverfasser: Ciou, Yan-Syun, Lin, Po-Han, Li, Wei-Ming, Lee, Kun-Mu, Liu, Ching-Yuan
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container_end_page 3551
container_issue 7
container_start_page 3538
container_title Journal of organic chemistry
container_volume 82
creator Ciou, Yan-Syun
Lin, Po-Han
Li, Wei-Ming
Lee, Kun-Mu
Liu, Ching-Yuan
description A variety of push–pull type organic dyes are facilely synthesized through the most atom-economical C–H/C–H dehydrogenative coupling reactions. After comprehensive synthetic optimizations, a broad substrate scope is achieved and functional groups, such as ester, ketone, nitrile, nitro, and triazene are well tolerated. The sensitive aldehyde group required for the conversion into anchoring groups for DSSCs applications is also compatible under present oxidant-containing reaction conditions. Based on this optimum C–H/C–H coupling approach, three new organic sensitizers are readily prepared and submitted to solar cell device fabrications, giving the power conversion efficiency (PCE) up to 4.85%. This work constitutes the first example that connects high atom-efficiency C–H/C–H green catalysis with dye-sensitized solar cell applications.
doi_str_mv 10.1021/acs.joc.7b00054
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title Cross-Dehydrogenative Coupling (CDC) as Key-Transformations to Various D−π–A Organic Dyes: C–H/C–H Synthetic Study Directed toward Dye-Sensitized Solar Cells Applications
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