Synthesis and characterization of S,N-heterotetracenes
The synthesis and optoelectronic properties of novel S,N-heterotetracenes consisting of fused heterocyclic thiophene and pyrrole rings are presented. Tetracyclic and benzannulated derivatives with a varying number and sequence of sulfur and nitrogen heteroatoms were synthesized in multistep syntheti...
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doaj-48ad7302792d402cbe476d45606e36002021-04-02T20:53:53ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972020-10-011612636264410.3762/bjoc.16.2141860-5397-16-214Synthesis and characterization of S,N-heterotetracenesAstrid Vogt0Florian Henne1Christoph Wetzel2Elena 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, GermanyThe synthesis and optoelectronic properties of novel S,N-heterotetracenes consisting of fused heterocyclic thiophene and pyrrole rings are presented. Tetracyclic and benzannulated derivatives with a varying number and sequence of sulfur and nitrogen heteroatoms were synthesized in multistep synthetic routes. A Buchwald–Hartwig amination of brominated precursors, thermolysis of azide precursors, and a Cadogan reaction of nitro-substituted precursors were successfully applied to eventually build-up pyrrole rings to stable and soluble fused systems. The various obtained heteroatom sequences ‘SSNS’ (SN4), ‘SNNS’ (SN4’’), and ‘NSSN’ (SN4’) allowed for evaluation of structure–property relationships relative to the sulfur analogue tetrathienoacene (‘SSSS’). In line with the results for the whole series of S,N-heteroacenes, we find that replacement of sulfur by nitrogen atoms in the tetra- and hexacyclic systems leads to a red-shift in absorption, a decrease in oxidation potential and energy gap. On the other hand, the replacement of a thiophene ring by benzene leads to the opposite effects.https://doi.org/10.3762/bjoc.16.214buchwald–hartwig aminationcadogan reactionoptoelectronic propertiess,n-heteroacenestructure–property relationship |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Astrid Vogt Florian Henne Christoph Wetzel Elena Mena-Osteritz Peter Bäuerle |
spellingShingle |
Astrid Vogt Florian Henne Christoph Wetzel Elena Mena-Osteritz Peter Bäuerle Synthesis and characterization of S,N-heterotetracenes Beilstein Journal of Organic Chemistry buchwald–hartwig amination cadogan reaction optoelectronic properties s,n-heteroacene structure–property relationship |
author_facet |
Astrid Vogt Florian Henne Christoph Wetzel Elena Mena-Osteritz Peter Bäuerle |
author_sort |
Astrid Vogt |
title |
Synthesis and characterization of S,N-heterotetracenes |
title_short |
Synthesis and characterization of S,N-heterotetracenes |
title_full |
Synthesis and characterization of S,N-heterotetracenes |
title_fullStr |
Synthesis and characterization of S,N-heterotetracenes |
title_full_unstemmed |
Synthesis and characterization of S,N-heterotetracenes |
title_sort |
synthesis and characterization of s,n-heterotetracenes |
publisher |
Beilstein-Institut |
series |
Beilstein Journal of Organic Chemistry |
issn |
1860-5397 |
publishDate |
2020-10-01 |
description |
The synthesis and optoelectronic properties of novel S,N-heterotetracenes consisting of fused heterocyclic thiophene and pyrrole rings are presented. Tetracyclic and benzannulated derivatives with a varying number and sequence of sulfur and nitrogen heteroatoms were synthesized in multistep synthetic routes. A Buchwald–Hartwig amination of brominated precursors, thermolysis of azide precursors, and a Cadogan reaction of nitro-substituted precursors were successfully applied to eventually build-up pyrrole rings to stable and soluble fused systems. The various obtained heteroatom sequences ‘SSNS’ (SN4), ‘SNNS’ (SN4’’), and ‘NSSN’ (SN4’) allowed for evaluation of structure–property relationships relative to the sulfur analogue tetrathienoacene (‘SSSS’). In line with the results for the whole series of S,N-heteroacenes, we find that replacement of sulfur by nitrogen atoms in the tetra- and hexacyclic systems leads to a red-shift in absorption, a decrease in oxidation potential and energy gap. On the other hand, the replacement of a thiophene ring by benzene leads to the opposite effects. |
topic |
buchwald–hartwig amination cadogan reaction optoelectronic properties s,n-heteroacene structure–property relationship |
url |
https://doi.org/10.3762/bjoc.16.214 |
work_keys_str_mv |
AT astridvogt synthesisandcharacterizationofsnheterotetracenes AT florianhenne synthesisandcharacterizationofsnheterotetracenes AT christophwetzel synthesisandcharacterizationofsnheterotetracenes AT elenamenaosteritz synthesisandcharacterizationofsnheterotetracenes AT peterbauerle synthesisandcharacterizationofsnheterotetracenes |
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1721546211945611264 |