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Cyclopentannulated Dihydrotetraazapentacenes
The transition‐metal‐catalyzed cyclization of bissilylethynylated N,N’‐dihydrotetraazapentacene (TIPS‐TAP‐H(2)) into bissilylated cyclopenta[fg,qr]pentacenes is reported. Depending on the catalyst either none, one or two silyl groups migrate and change their positions in the formed five‐membered rin...
| Autores principales: | , , , , , , , , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
John Wiley and Sons Inc.
2022
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9303544/ https://www.ncbi.nlm.nih.gov/pubmed/35020239 http://dx.doi.org/10.1002/chem.202104203 |
| _version_ | 1784751892437401600 |
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| author | Heckershoff, Robin Maier, Steffen Wurm, Thomas Biegger, Philipp Brödner, Kerstin Krämer, Petra Hoffmann, Marvin T. Eberle, Lukas Stein, Jana Rominger, Frank Rudolph, Matthias Freudenberg, Jan Dreuw, Andreas Hashmi, A. Stephen K. Bunz, Uwe H. F. |
| author_facet | Heckershoff, Robin Maier, Steffen Wurm, Thomas Biegger, Philipp Brödner, Kerstin Krämer, Petra Hoffmann, Marvin T. Eberle, Lukas Stein, Jana Rominger, Frank Rudolph, Matthias Freudenberg, Jan Dreuw, Andreas Hashmi, A. Stephen K. Bunz, Uwe H. F. |
| author_sort | Heckershoff, Robin |
| collection | PubMed |
| description | The transition‐metal‐catalyzed cyclization of bissilylethynylated N,N’‐dihydrotetraazapentacene (TIPS‐TAP‐H(2)) into bissilylated cyclopenta[fg,qr]pentacenes is reported. Depending on the catalyst either none, one or two silyl groups migrate and change their positions in the formed five‐membered rings. The optoelectronic properties are quite similar, whereas the packing motifs differ dramatically. Control experiments and quantum chemical calculations were performed to investigate the mechanism of the reaction and the selectivity of the silyl shift. |
| format | Online Article Text |
| id | pubmed-9303544 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2022 |
| publisher | John Wiley and Sons Inc. |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-93035442022-07-28 Cyclopentannulated Dihydrotetraazapentacenes Heckershoff, Robin Maier, Steffen Wurm, Thomas Biegger, Philipp Brödner, Kerstin Krämer, Petra Hoffmann, Marvin T. Eberle, Lukas Stein, Jana Rominger, Frank Rudolph, Matthias Freudenberg, Jan Dreuw, Andreas Hashmi, A. Stephen K. Bunz, Uwe H. F. Chemistry Research Articles The transition‐metal‐catalyzed cyclization of bissilylethynylated N,N’‐dihydrotetraazapentacene (TIPS‐TAP‐H(2)) into bissilylated cyclopenta[fg,qr]pentacenes is reported. Depending on the catalyst either none, one or two silyl groups migrate and change their positions in the formed five‐membered rings. The optoelectronic properties are quite similar, whereas the packing motifs differ dramatically. Control experiments and quantum chemical calculations were performed to investigate the mechanism of the reaction and the selectivity of the silyl shift. John Wiley and Sons Inc. 2022-02-02 2022-02-24 /pmc/articles/PMC9303544/ /pubmed/35020239 http://dx.doi.org/10.1002/chem.202104203 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 Heckershoff, Robin Maier, Steffen Wurm, Thomas Biegger, Philipp Brödner, Kerstin Krämer, Petra Hoffmann, Marvin T. Eberle, Lukas Stein, Jana Rominger, Frank Rudolph, Matthias Freudenberg, Jan Dreuw, Andreas Hashmi, A. Stephen K. Bunz, Uwe H. F. Cyclopentannulated Dihydrotetraazapentacenes |
| title | Cyclopentannulated Dihydrotetraazapentacenes |
| title_full | Cyclopentannulated Dihydrotetraazapentacenes |
| title_fullStr | Cyclopentannulated Dihydrotetraazapentacenes |
| title_full_unstemmed | Cyclopentannulated Dihydrotetraazapentacenes |
| title_short | Cyclopentannulated Dihydrotetraazapentacenes |
| title_sort | cyclopentannulated dihydrotetraazapentacenes |
| topic | Research Articles |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9303544/ https://www.ncbi.nlm.nih.gov/pubmed/35020239 http://dx.doi.org/10.1002/chem.202104203 |
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