Imidazolyl‐Substituted Benzo‐ and Naphthodithiophenes as Precursors for the Synthesis of Transient Open‐Shell Quinoids
Abstract The synthesis of three novel imidazolyl‐substituted sulfur‐containing heteroacenes is reported. These heteroacenes consisting of annelated benzo‐ and naphthothiophenes serve as precursors for the generation of open‐shell quinoid heteroacenes by oxidation with alkaline ferric cyanide. Spectr...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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Wiley-VCH
2023-11-01
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| Series: | ChemistryOpen |
| Subjects: | |
| Online Access: | https://doi.org/10.1002/open.202300003 |
| _version_ | 1797454732464226304 |
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| author | Peng Hou Sebastian Peschtrich Dr. Wolfram Feuerstein Dr. Roland Schoch Prof. Dr. Stephan Hohloch Prof. Dr. Frank Breher Prof. Dr. Jan Paradies |
| author_facet | Peng Hou Sebastian Peschtrich Dr. Wolfram Feuerstein Dr. Roland Schoch Prof. Dr. Stephan Hohloch Prof. Dr. Frank Breher Prof. Dr. Jan Paradies |
| author_sort | Peng Hou |
| collection | DOAJ |
| description | Abstract The synthesis of three novel imidazolyl‐substituted sulfur‐containing heteroacenes is reported. These heteroacenes consisting of annelated benzo‐ and naphthothiophenes serve as precursors for the generation of open‐shell quinoid heteroacenes by oxidation with alkaline ferric cyanide. Spectroscopic and computational experiments support the formation of reactive open‐shell quinoids, which, however, quickly produce paramagnetic polymeric material. |
| first_indexed | 2024-03-09T15:41:21Z |
| format | Article |
| id | doaj.art-e682b584b15c49b08dd45bb951cbfadd |
| institution | Directory Open Access Journal |
| issn | 2191-1363 |
| language | English |
| last_indexed | 2024-03-09T15:41:21Z |
| publishDate | 2023-11-01 |
| publisher | Wiley-VCH |
| record_format | Article |
| series | ChemistryOpen |
| spelling | doaj.art-e682b584b15c49b08dd45bb951cbfadd2023-11-25T02:50:28ZengWiley-VCHChemistryOpen2191-13632023-11-011211n/an/a10.1002/open.202300003Imidazolyl‐Substituted Benzo‐ and Naphthodithiophenes as Precursors for the Synthesis of Transient Open‐Shell QuinoidsPeng Hou0Sebastian Peschtrich1Dr. Wolfram Feuerstein2Dr. Roland Schoch3Prof. Dr. Stephan Hohloch4Prof. Dr. Frank Breher5Prof. Dr. Jan Paradies6Chemistry Department Paderborn University Warburger Strasse 100 33098 Paderborn GermanyChemistry Department Paderborn University Warburger Strasse 100 33098 Paderborn GermanyInstitute of Inorganic Chemistry Karlsruhe Institute of Technology (KIT) Engesserstraße 15 76131 Karlsruhe GermanyChemistry Department Paderborn University Warburger Strasse 100 33098 Paderborn GermanyDepartment of General, Inorganic and Theoretical Chemistry University of Innsbruck Innrain 80–82 6020 Innsbruck AustriaInstitute of Inorganic Chemistry Karlsruhe Institute of Technology (KIT) Engesserstraße 15 76131 Karlsruhe GermanyChemistry Department Paderborn University Warburger Strasse 100 33098 Paderborn GermanyAbstract The synthesis of three novel imidazolyl‐substituted sulfur‐containing heteroacenes is reported. These heteroacenes consisting of annelated benzo‐ and naphthothiophenes serve as precursors for the generation of open‐shell quinoid heteroacenes by oxidation with alkaline ferric cyanide. Spectroscopic and computational experiments support the formation of reactive open‐shell quinoids, which, however, quickly produce paramagnetic polymeric material.https://doi.org/10.1002/open.202300003density functional theoryheteroacenequinoidthiopheneUV/vis spectroscopy |
| spellingShingle | Peng Hou Sebastian Peschtrich Dr. Wolfram Feuerstein Dr. Roland Schoch Prof. Dr. Stephan Hohloch Prof. Dr. Frank Breher Prof. Dr. Jan Paradies Imidazolyl‐Substituted Benzo‐ and Naphthodithiophenes as Precursors for the Synthesis of Transient Open‐Shell Quinoids ChemistryOpen density functional theory heteroacene quinoid thiophene UV/vis spectroscopy |
| title | Imidazolyl‐Substituted Benzo‐ and Naphthodithiophenes as Precursors for the Synthesis of Transient Open‐Shell Quinoids |
| title_full | Imidazolyl‐Substituted Benzo‐ and Naphthodithiophenes as Precursors for the Synthesis of Transient Open‐Shell Quinoids |
| title_fullStr | Imidazolyl‐Substituted Benzo‐ and Naphthodithiophenes as Precursors for the Synthesis of Transient Open‐Shell Quinoids |
| title_full_unstemmed | Imidazolyl‐Substituted Benzo‐ and Naphthodithiophenes as Precursors for the Synthesis of Transient Open‐Shell Quinoids |
| title_short | Imidazolyl‐Substituted Benzo‐ and Naphthodithiophenes as Precursors for the Synthesis of Transient Open‐Shell Quinoids |
| title_sort | imidazolyl substituted benzo and naphthodithiophenes as precursors for the synthesis of transient open shell quinoids |
| topic | density functional theory heteroacene quinoid thiophene UV/vis spectroscopy |
| url | https://doi.org/10.1002/open.202300003 |
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