Selenophene-containing heterotriacenes by a C–Se coupling/cyclization reaction
A new novel family of tricyclic sulfur and/or selenium-containing heterotriacenes 2–4 with an increasing number of selenium (Se) atoms is presented. The heterotriacene derivatives were synthesized in multistep synthetic routes and the crucial cyclization steps to the stable and soluble fused systems...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2019-06-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.15.138 |
| _version_ | 1818855145374482432 |
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| author | Pierre-Olivier Schwartz Sebastian Förtsch Astrid Vogt Elena Mena-Osteritz Peter Bäuerle |
| author_facet | Pierre-Olivier Schwartz Sebastian Förtsch Astrid Vogt Elena Mena-Osteritz Peter Bäuerle |
| author_sort | Pierre-Olivier Schwartz |
| collection | DOAJ |
| description | A new novel family of tricyclic sulfur and/or selenium-containing heterotriacenes 2–4 with an increasing number of selenium (Se) atoms is presented. The heterotriacene derivatives were synthesized in multistep synthetic routes and the crucial cyclization steps to the stable and soluble fused systems were achieved by copper-catalyzed C–S and C–Se coupling/cyclization reactions. Structures and packing motifs in the solid state were elucidated by single crystal X-ray analysis and XRD powder measurements. Comparison of the optoelectronic properties provides interesting structure–property relationships and gives valuable insights into the role of heteroatoms within the series of the heterotriacenes. Electrooxidative polymerization led to the corresponding poly(heterotriacene)s P2–P4. |
| first_indexed | 2024-12-19T08:03:57Z |
| format | Article |
| id | doaj.art-82f2bb8f60c04c25958c36a5b80da1ff |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-19T08:03:57Z |
| publishDate | 2019-06-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-82f2bb8f60c04c25958c36a5b80da1ff2022-12-21T20:29:48ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972019-06-011511379139310.3762/bjoc.15.1381860-5397-15-138Selenophene-containing heterotriacenes by a C–Se coupling/cyclization reactionPierre-Olivier Schwartz0Sebastian Förtsch1Astrid Vogt2Elena Mena-Osteritz3Peter Bäuerle4Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, GermanyInstitute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, GermanyInstitute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, GermanyInstitute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, GermanyInstitute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, GermanyA new novel family of tricyclic sulfur and/or selenium-containing heterotriacenes 2–4 with an increasing number of selenium (Se) atoms is presented. The heterotriacene derivatives were synthesized in multistep synthetic routes and the crucial cyclization steps to the stable and soluble fused systems were achieved by copper-catalyzed C–S and C–Se coupling/cyclization reactions. Structures and packing motifs in the solid state were elucidated by single crystal X-ray analysis and XRD powder measurements. Comparison of the optoelectronic properties provides interesting structure–property relationships and gives valuable insights into the role of heteroatoms within the series of the heterotriacenes. Electrooxidative polymerization led to the corresponding poly(heterotriacene)s P2–P4.https://doi.org/10.3762/bjoc.15.138conducting polymerC–S couplingC–Se couplingheteroaceneselenophene |
| spellingShingle | Pierre-Olivier Schwartz Sebastian Förtsch Astrid Vogt Elena Mena-Osteritz Peter Bäuerle Selenophene-containing heterotriacenes by a C–Se coupling/cyclization reaction Beilstein Journal of Organic Chemistry conducting polymer C–S coupling C–Se coupling heteroacene selenophene |
| title | Selenophene-containing heterotriacenes by a C–Se coupling/cyclization reaction |
| title_full | Selenophene-containing heterotriacenes by a C–Se coupling/cyclization reaction |
| title_fullStr | Selenophene-containing heterotriacenes by a C–Se coupling/cyclization reaction |
| title_full_unstemmed | Selenophene-containing heterotriacenes by a C–Se coupling/cyclization reaction |
| title_short | Selenophene-containing heterotriacenes by a C–Se coupling/cyclization reaction |
| title_sort | selenophene containing heterotriacenes by a c se coupling cyclization reaction |
| topic | conducting polymer C–S coupling C–Se coupling heteroacene selenophene |
| url | https://doi.org/10.3762/bjoc.15.138 |
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