n]Helicene Diimides (n = 5, 6, and 7) : Through-Bond versus Through-Space Conjugation
The interactions between auxochromic groups in π-conjugated functional molecules dictate their electronic properties. From the standpoint of potential applications, understanding and control of such interactions is a vital requirement for the material design. In this communication, we describe the design, synthesis, and functional properties of a novel class of helically chiral diimide molecules, namely, [n]HDI-OMe (n = 5, 6, and 7), in which two imide units are connected via an [n]helicene skeleton. The experimental results supported by quantum chemical calculations reveal that the helical backbone in these molecules offers not only through-bond but also through-space conjugation between imide groups, which leads to distinct optical and electrochemical properties when compared to the related [n]helicenes and rylene diimides.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2020 |
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| Erschienen: |
2020 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:142 |
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| Enthalten in: |
Journal of the American Chemical Society - 142(2020), 51 vom: 23. Dez., Seite 21298-21303 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Saal, Fridolin [VerfasserIn] |
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| Links: |
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| Themen: |
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| Anmerkungen: |
Date Revised 23.12.2020 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1021/jacs.0c11053 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM318806207 |
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| 245 | 1 | 0 | |a n]Helicene Diimides (n = 5, 6, and 7) |b Through-Bond versus Through-Space Conjugation |
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| 500 | |a Date Revised 23.12.2020 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a The interactions between auxochromic groups in π-conjugated functional molecules dictate their electronic properties. From the standpoint of potential applications, understanding and control of such interactions is a vital requirement for the material design. In this communication, we describe the design, synthesis, and functional properties of a novel class of helically chiral diimide molecules, namely, [n]HDI-OMe (n = 5, 6, and 7), in which two imide units are connected via an [n]helicene skeleton. The experimental results supported by quantum chemical calculations reveal that the helical backbone in these molecules offers not only through-bond but also through-space conjugation between imide groups, which leads to distinct optical and electrochemical properties when compared to the related [n]helicenes and rylene diimides | ||
| 650 | 4 | |a Journal Article | |
| 700 | 1 | |a Zhang, Fangyuan |e verfasserin |4 aut | |
| 700 | 1 | |a Holzapfel, Marco |e verfasserin |4 aut | |
| 700 | 1 | |a Stolte, Matthias |e verfasserin |4 aut | |
| 700 | 1 | |a Michail, Evripidis |e verfasserin |4 aut | |
| 700 | 1 | |a Moos, Michael |e verfasserin |4 aut | |
| 700 | 1 | |a Schmiedel, Alexander |e verfasserin |4 aut | |
| 700 | 1 | |a Krause, Ana-Maria |e verfasserin |4 aut | |
| 700 | 1 | |a Lambert, Christoph |e verfasserin |4 aut | |
| 700 | 1 | |a Würthner, Frank |e verfasserin |4 aut | |
| 700 | 1 | |a Ravat, Prince |e verfasserin |4 aut | |
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