Synthesis of Novel 3,6-Dithienyl Diketopyrrolopyrrole Dyes by Direct C-H Arylation
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 a...
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| Format: | Article |
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MDPI AG
2020-05-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/10/2349 |
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| author | Amsalu Efrem Yemene Vishwesh Venkatraman David Moe Almenningen Bård Helge Hoff Odd Reidar Gautun |
| author_facet | Amsalu Efrem Yemene Vishwesh Venkatraman David Moe Almenningen Bård Helge Hoff Odd Reidar Gautun |
| author_sort | Amsalu Efrem Yemene |
| collection | DOAJ |
| description | 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 sp<sup>2</sup>−sp<sup>2</sup> 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%. |
| first_indexed | 2024-03-10T19:46:15Z |
| format | Article |
| id | doaj.art-f8bf74d753d3465f80a558d8d333e1f2 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T19:46:15Z |
| publishDate | 2020-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-f8bf74d753d3465f80a558d8d333e1f22023-11-20T00:50:04ZengMDPI AGMolecules1420-30492020-05-012510234910.3390/molecules25102349Synthesis of Novel 3,6-Dithienyl Diketopyrrolopyrrole Dyes by Direct C-H ArylationAmsalu Efrem Yemene0Vishwesh Venkatraman1David Moe Almenningen2Bård Helge Hoff3Odd Reidar Gautun4Department of Chemistry, Norwegian University of Science and Technology (NTNU), N-7491 Trondheim, NorwayDepartment of Chemistry, Norwegian University of Science and Technology (NTNU), N-7491 Trondheim, NorwayDepartment of Chemistry, Norwegian University of Science and Technology (NTNU), N-7491 Trondheim, NorwayDepartment of Chemistry, Norwegian University of Science and Technology (NTNU), N-7491 Trondheim, NorwayDepartment of Chemistry, Norwegian University of Science and Technology (NTNU), N-7491 Trondheim, NorwayDirect 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 sp<sup>2</sup>−sp<sup>2</sup> 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%.https://www.mdpi.com/1420-3049/25/10/2349direct C-H arylationdye-sensitized solar cellsdiketopyrrolopyrrolephenothiazinetriarylaminedye |
| spellingShingle | Amsalu Efrem Yemene Vishwesh Venkatraman David Moe Almenningen Bård Helge Hoff Odd Reidar Gautun Synthesis of Novel 3,6-Dithienyl Diketopyrrolopyrrole Dyes by Direct C-H Arylation Molecules direct C-H arylation dye-sensitized solar cells diketopyrrolopyrrole phenothiazine triarylamine dye |
| title | Synthesis of Novel 3,6-Dithienyl Diketopyrrolopyrrole Dyes by Direct C-H Arylation |
| title_full | Synthesis of Novel 3,6-Dithienyl Diketopyrrolopyrrole Dyes by Direct C-H Arylation |
| title_fullStr | Synthesis of Novel 3,6-Dithienyl Diketopyrrolopyrrole Dyes by Direct C-H Arylation |
| title_full_unstemmed | Synthesis of Novel 3,6-Dithienyl Diketopyrrolopyrrole Dyes by Direct C-H Arylation |
| title_short | Synthesis of Novel 3,6-Dithienyl Diketopyrrolopyrrole Dyes by Direct C-H Arylation |
| title_sort | synthesis of novel 3 6 dithienyl diketopyrrolopyrrole dyes by direct c h arylation |
| topic | direct C-H arylation dye-sensitized solar cells diketopyrrolopyrrole phenothiazine triarylamine dye |
| url | https://www.mdpi.com/1420-3049/25/10/2349 |
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