Polycyclic Aromatic Hydrocarbons Containing A Pyrrolopyridazine Core
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim..
Polycyclic aromatic azomethine ylides (PAMYs) are versatile building blocks for the bottom-up construction of unprecedented nitrogen-containing polycyclic aromatic hydrocarbons (N-PAHs). Here, we demonstrate the 1,3-dipolar cycloaddition between PAMY and 1,4-diphenylbut-2-yne-1,4-dione and the subsequent condensation reaction with hydrazine, which led to unique N-PAHs with a phenyl-substituted pyrrolopyridazine core (PP-1 and PP-2). The molecular structures of pristine PP-1 and tert-butyl-substituted PP-2 were verified by NMR spectroscopy and mass spectrometry. Moreover, the structure of PP-2 was unambiguously elucidated by X-ray single crystal analysis. The optoelectronic properties were investigated by solvent-dependent UV-Vis absorption and fluorescence emission spectroscopy as well as cyclic voltammetry. Additionally, density functional theory (DFT) calculations showed that PP-1 and PP-2 exhibit push-pull behavior. Furthermore, in situ EPR/UV-Vis-NIR spectroelectrochemistry allowed the detailed insight into the spectroscopic properties and spin distribution of radical cation species of PP-2.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2019 |
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| Erschienen: |
2019 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:84 |
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| Enthalten in: |
ChemPlusChem - 84(2019), 6 vom: 20. Juni, Seite 613-618 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Richter, Marcus [VerfasserIn] |
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| Links: |
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| Themen: |
Azomethine ylides |
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| Anmerkungen: |
Date Completed 22.04.2020 Date Revised 22.04.2020 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1002/cplu.201900031 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM305424319 |
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| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. | ||
| 520 | |a Polycyclic aromatic azomethine ylides (PAMYs) are versatile building blocks for the bottom-up construction of unprecedented nitrogen-containing polycyclic aromatic hydrocarbons (N-PAHs). Here, we demonstrate the 1,3-dipolar cycloaddition between PAMY and 1,4-diphenylbut-2-yne-1,4-dione and the subsequent condensation reaction with hydrazine, which led to unique N-PAHs with a phenyl-substituted pyrrolopyridazine core (PP-1 and PP-2). The molecular structures of pristine PP-1 and tert-butyl-substituted PP-2 were verified by NMR spectroscopy and mass spectrometry. Moreover, the structure of PP-2 was unambiguously elucidated by X-ray single crystal analysis. The optoelectronic properties were investigated by solvent-dependent UV-Vis absorption and fluorescence emission spectroscopy as well as cyclic voltammetry. Additionally, density functional theory (DFT) calculations showed that PP-1 and PP-2 exhibit push-pull behavior. Furthermore, in situ EPR/UV-Vis-NIR spectroelectrochemistry allowed the detailed insight into the spectroscopic properties and spin distribution of radical cation species of PP-2 | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 4 | |a azomethine ylides | |
| 650 | 4 | |a cycloaddition | |
| 650 | 4 | |a heterocycles | |
| 650 | 4 | |a polycyclic aromatic hydrocarbons | |
| 650 | 4 | |a radical cations | |
| 700 | 1 | |a Fu, Yubin |e verfasserin |4 aut | |
| 700 | 1 | |a Dmitrieva, Evgenia |e verfasserin |4 aut | |
| 700 | 1 | |a Weigand, Jan J |e verfasserin |4 aut | |
| 700 | 1 | |a Popov, Alexey |e verfasserin |4 aut | |
| 700 | 1 | |a Berger, Reinhard |e verfasserin |4 aut | |
| 700 | 1 | |a Liu, Junzhi |e verfasserin |4 aut | |
| 700 | 1 | |a Feng, Xinliang |e verfasserin |4 aut | |
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