Synthesis and Characterization of Bis[1]benzothieno[3,2-b:2′,3′-d]pyrroles: Quantitative Effects of Benzannulation on Dithieno[3,2-b:2′,3′-d]pyrroles
The synthesis of four N-functionalized bis[1]benzothieno[3,2-b:2′,3′-d]pyrroles (BBTPs) is reported in order to provide a more detailed characterization of these fused-ring units, as well as increase the scope of known BBTP units available for application to conjugated materials. The optical, electr...
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| Format: | Article |
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MDPI AG
2018-09-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/23/9/2279 |
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| author | Rylan M. W. Wolfe Evan W. Culver Seth C. Rasmussen |
| author_facet | Rylan M. W. Wolfe Evan W. Culver Seth C. Rasmussen |
| author_sort | Rylan M. W. Wolfe |
| collection | DOAJ |
| description | The synthesis of four N-functionalized bis[1]benzothieno[3,2-b:2′,3′-d]pyrroles (BBTPs) is reported in order to provide a more detailed characterization of these fused-ring units, as well as increase the scope of known BBTP units available for application to conjugated materials. The optical, electronic, and structural properties of the resulting BBTP units have been compared to the parent N-alkyl- and N-aryl-dithieno[3,2-b:2′,3′-d]pyrroles (DTPs), as well as their corresponding 2,6-diphenyl derivatives, in order to fully quantify the relative electronic effects resulting from benzannulation of the parent DTP building block. Such comparative analysis reveals that benzannulation results in a red-shifted absorbance, but to a lesser extent than simple phenyl-capping of the DTP. More surprising is that benzannulation results in stabilization of the BBTP HOMO, compared to the destabilization normally observed with extending the conjugation length of the backbone. |
| first_indexed | 2024-12-10T18:38:00Z |
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| id | doaj.art-2575f2b400d045469160ba55c0fa47d8 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-10T18:38:00Z |
| publishDate | 2018-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-2575f2b400d045469160ba55c0fa47d82022-12-22T01:37:44ZengMDPI AGMolecules1420-30492018-09-01239227910.3390/molecules23092279molecules23092279Synthesis and Characterization of Bis[1]benzothieno[3,2-b:2′,3′-d]pyrroles: Quantitative Effects of Benzannulation on Dithieno[3,2-b:2′,3′-d]pyrrolesRylan M. W. Wolfe0Evan W. Culver1Seth C. Rasmussen2Department of Chemistry and Biochemistry, North Dakota State University, NDSU Dept. 2735, P.O. Box 6050, Fargo, ND 58108-6050, USADepartment of Chemistry and Biochemistry, North Dakota State University, NDSU Dept. 2735, P.O. Box 6050, Fargo, ND 58108-6050, USADepartment of Chemistry and Biochemistry, North Dakota State University, NDSU Dept. 2735, P.O. Box 6050, Fargo, ND 58108-6050, USAThe synthesis of four N-functionalized bis[1]benzothieno[3,2-b:2′,3′-d]pyrroles (BBTPs) is reported in order to provide a more detailed characterization of these fused-ring units, as well as increase the scope of known BBTP units available for application to conjugated materials. The optical, electronic, and structural properties of the resulting BBTP units have been compared to the parent N-alkyl- and N-aryl-dithieno[3,2-b:2′,3′-d]pyrroles (DTPs), as well as their corresponding 2,6-diphenyl derivatives, in order to fully quantify the relative electronic effects resulting from benzannulation of the parent DTP building block. Such comparative analysis reveals that benzannulation results in a red-shifted absorbance, but to a lesser extent than simple phenyl-capping of the DTP. More surprising is that benzannulation results in stabilization of the BBTP HOMO, compared to the destabilization normally observed with extending the conjugation length of the backbone.http://www.mdpi.com/1420-3049/23/9/2279fused-ring thiophenesheteroacenesdithieno[3,2-b:2′,3′-d]pyrrolesbenzannulationstructure-function relationships |
| spellingShingle | Rylan M. W. Wolfe Evan W. Culver Seth C. Rasmussen Synthesis and Characterization of Bis[1]benzothieno[3,2-b:2′,3′-d]pyrroles: Quantitative Effects of Benzannulation on Dithieno[3,2-b:2′,3′-d]pyrroles Molecules fused-ring thiophenes heteroacenes dithieno[3,2-b:2′,3′-d]pyrroles benzannulation structure-function relationships |
| title | Synthesis and Characterization of Bis[1]benzothieno[3,2-b:2′,3′-d]pyrroles: Quantitative Effects of Benzannulation on Dithieno[3,2-b:2′,3′-d]pyrroles |
| title_full | Synthesis and Characterization of Bis[1]benzothieno[3,2-b:2′,3′-d]pyrroles: Quantitative Effects of Benzannulation on Dithieno[3,2-b:2′,3′-d]pyrroles |
| title_fullStr | Synthesis and Characterization of Bis[1]benzothieno[3,2-b:2′,3′-d]pyrroles: Quantitative Effects of Benzannulation on Dithieno[3,2-b:2′,3′-d]pyrroles |
| title_full_unstemmed | Synthesis and Characterization of Bis[1]benzothieno[3,2-b:2′,3′-d]pyrroles: Quantitative Effects of Benzannulation on Dithieno[3,2-b:2′,3′-d]pyrroles |
| title_short | Synthesis and Characterization of Bis[1]benzothieno[3,2-b:2′,3′-d]pyrroles: Quantitative Effects of Benzannulation on Dithieno[3,2-b:2′,3′-d]pyrroles |
| title_sort | synthesis and characterization of bis 1 benzothieno 3 2 b 2 3 d pyrroles quantitative effects of benzannulation on dithieno 3 2 b 2 3 d pyrroles |
| topic | fused-ring thiophenes heteroacenes dithieno[3,2-b:2′,3′-d]pyrroles benzannulation structure-function relationships |
| url | http://www.mdpi.com/1420-3049/23/9/2279 |
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