The Radical Anion, Dianion and Electron Transport Properties of Tetraiodotetraazapentacene

Tetraiodotetraazapentacene I(4)TAP, the last missing derivative in the series of halogenated silylated tetraazapentacenes, was synthesized via condensation chemistry from a TIPS‐ethynylated diaminobenzothiadiazol in three steps. Single and double reduction furnished its air‐stable monoanion and rela...

Descripción completa

Detalles Bibliográficos
Autores principales: Wiesner, Thomas, Wu, Zhu, Han, Jie, Ji, Lei, Friedrich, Alexandra, Krummenacher, Ivo, Moos, Michael, Lambert, Christoph, Braunschweig, Holger, Rudin, Benjamin, Reiss, Hilmar, Tverskoy, Olena, Rominger, Frank, Dreuw, Andreas, Marder, Todd B., Freudenberg, Jan, Bunz, Uwe H. F.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Research Articles
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10092590/
https://www.ncbi.nlm.nih.gov/pubmed/35916326
http://dx.doi.org/10.1002/chem.202201919
_version_ 1785023382393192448
author Wiesner, Thomas
Wu, Zhu
Han, Jie
Ji, Lei
Friedrich, Alexandra
Krummenacher, Ivo
Moos, Michael
Lambert, Christoph
Braunschweig, Holger
Rudin, Benjamin
Reiss, Hilmar
Tverskoy, Olena
Rominger, Frank
Dreuw, Andreas
Marder, Todd B.
Freudenberg, Jan
Bunz, Uwe H. F.
author_facet Wiesner, Thomas
Wu, Zhu
Han, Jie
Ji, Lei
Friedrich, Alexandra
Krummenacher, Ivo
Moos, Michael
Lambert, Christoph
Braunschweig, Holger
Rudin, Benjamin
Reiss, Hilmar
Tverskoy, Olena
Rominger, Frank
Dreuw, Andreas
Marder, Todd B.
Freudenberg, Jan
Bunz, Uwe H. F.
author_sort Wiesner, Thomas
collection PubMed
description Tetraiodotetraazapentacene I(4)TAP, the last missing derivative in the series of halogenated silylated tetraazapentacenes, was synthesized via condensation chemistry from a TIPS‐ethynylated diaminobenzothiadiazol in three steps. Single and double reduction furnished its air‐stable monoanion and relatively air‐stable dianion, both of which were characterized by crystallography. All three species are structurally and spectroscopically compared to non‐halogenated TAP and Br(4)TAP. I(4)TAP is an n‐channel material in thin‐film transistors with average electron mobilities exceeding 1 cm(2) (Vs)(−1).
format Online
Article
Text
id pubmed-10092590
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-100925902023-04-13 The Radical Anion, Dianion and Electron Transport Properties of Tetraiodotetraazapentacene Wiesner, Thomas Wu, Zhu Han, Jie Ji, Lei Friedrich, Alexandra Krummenacher, Ivo Moos, Michael Lambert, Christoph Braunschweig, Holger Rudin, Benjamin Reiss, Hilmar Tverskoy, Olena Rominger, Frank Dreuw, Andreas Marder, Todd B. Freudenberg, Jan Bunz, Uwe H. F. Chemistry Research Articles Tetraiodotetraazapentacene I(4)TAP, the last missing derivative in the series of halogenated silylated tetraazapentacenes, was synthesized via condensation chemistry from a TIPS‐ethynylated diaminobenzothiadiazol in three steps. Single and double reduction furnished its air‐stable monoanion and relatively air‐stable dianion, both of which were characterized by crystallography. All three species are structurally and spectroscopically compared to non‐halogenated TAP and Br(4)TAP. I(4)TAP is an n‐channel material in thin‐film transistors with average electron mobilities exceeding 1 cm(2) (Vs)(−1). John Wiley and Sons Inc. 2022-10-25 2022-12-09 /pmc/articles/PMC10092590/ /pubmed/35916326 http://dx.doi.org/10.1002/chem.202201919 Text en © 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Articles
Wiesner, Thomas
Wu, Zhu
Han, Jie
Ji, Lei
Friedrich, Alexandra
Krummenacher, Ivo
Moos, Michael
Lambert, Christoph
Braunschweig, Holger
Rudin, Benjamin
Reiss, Hilmar
Tverskoy, Olena
Rominger, Frank
Dreuw, Andreas
Marder, Todd B.
Freudenberg, Jan
Bunz, Uwe H. F.
The Radical Anion, Dianion and Electron Transport Properties of Tetraiodotetraazapentacene
title The Radical Anion, Dianion and Electron Transport Properties of Tetraiodotetraazapentacene
title_full The Radical Anion, Dianion and Electron Transport Properties of Tetraiodotetraazapentacene
title_fullStr The Radical Anion, Dianion and Electron Transport Properties of Tetraiodotetraazapentacene
title_full_unstemmed The Radical Anion, Dianion and Electron Transport Properties of Tetraiodotetraazapentacene
title_short The Radical Anion, Dianion and Electron Transport Properties of Tetraiodotetraazapentacene
title_sort radical anion, dianion and electron transport properties of tetraiodotetraazapentacene
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10092590/
https://www.ncbi.nlm.nih.gov/pubmed/35916326
http://dx.doi.org/10.1002/chem.202201919
work_keys_str_mv AT wiesnerthomas theradicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT wuzhu theradicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT hanjie theradicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT jilei theradicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT friedrichalexandra theradicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT krummenacherivo theradicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT moosmichael theradicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT lambertchristoph theradicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT braunschweigholger theradicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT rudinbenjamin theradicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT reisshilmar theradicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT tverskoyolena theradicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT romingerfrank theradicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT dreuwandreas theradicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT mardertoddb theradicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT freudenbergjan theradicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT bunzuwehf theradicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT wiesnerthomas radicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT wuzhu radicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT hanjie radicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT jilei radicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT friedrichalexandra radicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT krummenacherivo radicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT moosmichael radicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT lambertchristoph radicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT braunschweigholger radicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT rudinbenjamin radicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT reisshilmar radicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT tverskoyolena radicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT romingerfrank radicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT dreuwandreas radicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT mardertoddb radicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT freudenbergjan radicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene
AT bunzuwehf radicalaniondianionandelectrontransportpropertiesoftetraiodotetraazapentacene

Ejemplares similares