Diazulenorubicene as a Non-benzenoid Isomer of peri-Tetracene with Two Sets of 5/7/5 Membered Rings Showing Good Semiconducting Properties
© 2023 Wiley-VCH GmbH..
Non-benzenoid polycyclic aromatic hydrocarbons (PAHs) have received a lot of attention because of their unique optical, electronic, and magnetic properties, but their synthesis remains challenging. Herein, we report a non-benzenoid isomer of peri-tetracene, diazulenorubicene (DAR), with two sets of 5/7/5 membered rings synthesized by a (3+2) annulation reaction. Compared with the precursor containing only 5/7 membered rings, the newly formed five membered rings switch the aromaticity of the original heptagon/pentagon from antiaromatic/aromatic to non-aromatic/antiaromatic respectively, modify the intermolecular packing modes, and lower the LUMO levels. Notably, compound 2 b (DAR-TMS) shows p-type semiconducting properties with a hole mobility up to 1.27 cm2 V-1 s-1 . Moreover, further extension to larger non-benzenoid PAHs with 19 rings was achieved through on-surface chemistry from the DAR derivative with one alkynyl group.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2023 |
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| Erschienen: |
2023 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:62 |
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| Enthalten in: |
Angewandte Chemie (International ed. in English) - 62(2023), 39 vom: 25. Sept., Seite e202304632 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Qin, Liyuan [VerfasserIn] |
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| Links: |
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| Themen: |
Annulation |
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| Anmerkungen: |
Date Revised 18.09.2023 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1002/anie.202304632 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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NLM358405092 |
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| 245 | 1 | 0 | |a Diazulenorubicene as a Non-benzenoid Isomer of peri-Tetracene with Two Sets of 5/7/5 Membered Rings Showing Good Semiconducting Properties |
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| 520 | |a © 2023 Wiley-VCH GmbH. | ||
| 520 | |a Non-benzenoid polycyclic aromatic hydrocarbons (PAHs) have received a lot of attention because of their unique optical, electronic, and magnetic properties, but their synthesis remains challenging. Herein, we report a non-benzenoid isomer of peri-tetracene, diazulenorubicene (DAR), with two sets of 5/7/5 membered rings synthesized by a (3+2) annulation reaction. Compared with the precursor containing only 5/7 membered rings, the newly formed five membered rings switch the aromaticity of the original heptagon/pentagon from antiaromatic/aromatic to non-aromatic/antiaromatic respectively, modify the intermolecular packing modes, and lower the LUMO levels. Notably, compound 2 b (DAR-TMS) shows p-type semiconducting properties with a hole mobility up to 1.27 cm2 V-1 s-1 . Moreover, further extension to larger non-benzenoid PAHs with 19 rings was achieved through on-surface chemistry from the DAR derivative with one alkynyl group | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Annulation | |
| 650 | 4 | |a Aromaticity | |
| 650 | 4 | |a Fused Ring Systems | |
| 650 | 4 | |a Semiconducting Properties | |
| 650 | 4 | |a on-Surface Synthesis | |
| 700 | 1 | |a Huang, Yan-Ying |e verfasserin |4 aut | |
| 700 | 1 | |a Wu, Botao |e verfasserin |4 aut | |
| 700 | 1 | |a Pan, Jinliang |e verfasserin |4 aut | |
| 700 | 1 | |a Yang, Junfang |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Jing |e verfasserin |4 aut | |
| 700 | 1 | |a Han, Guangchao |e verfasserin |4 aut | |
| 700 | 1 | |a Yang, Suyu |e verfasserin |4 aut | |
| 700 | 1 | |a Chen, Liangliang |e verfasserin |4 aut | |
| 700 | 1 | |a Yin, Zheng |e verfasserin |4 aut | |
| 700 | 1 | |a Shu, Yilin |e verfasserin |4 aut | |
| 700 | 1 | |a Jiang, Lang |e verfasserin |4 aut | |
| 700 | 1 | |a Yi, Yuanping |e verfasserin |4 aut | |
| 700 | 1 | |a Peng, Qian |e verfasserin |4 aut | |
| 700 | 1 | |a Zhou, Xiong |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Cheng |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Guanxin |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Xi-Sha |e verfasserin |4 aut | |
| 700 | 1 | |a Wu, Kai |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Deqing |e verfasserin |4 aut | |
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