- AutorIn
- Marcus Richter Technische Universität Dresden, Faculty of Chemistry and Food Chemistry, Institute for Molecular Functional Materials, Center for Advancing Electronics
- Yubin FuTechnische Universität Dresden, Faculty of Chemistry and Food Chemistry, Institute for Molecular Functional Materials, Center for Advancing Electronics
- Evgenia Dmitrieva
- Jan J. Weigand
- Alexej Popov
- Reinhard Berger
- Junzhi Liu
- Xinliang Feng
- Titel
- Polycyclic Aromatic Hydrocarbon Containing A Pyrrolopyridazine Core
- Zitierfähige Url:
- https://nbn-resolving.org/urn:nbn:de:bsz:14-qucosa2-731404
- Quellenangabe
- ChemPlusChem Erscheinungsort: Weinheim
Verlag: Wiley-VCH
Erscheinungsjahr: 2019
Jahrgang: 84
Heft: 6
Seiten: 613-618
E-ISSN: 2192-6506 - Erstveröffentlichung
- 2019
- Abstract (EN)
- Polycyclic aromatic azomethine ylide (PAMY) is a versatile building block 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 as well as the subsequent condensation reaction with hydrazine, which led to synthesis of 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 and mass spectroscopy. 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, the density functional theory (DFT) calculations exhibited a push-pull behavior for PP-1 and PP-2. Furthermore, the 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.
- Andere Ausgabe
- Link zum Artikel der zuerst in der Zeitschrift 'ChemPlusChem' erschienen ist
DOI: 10.1002/cplu.201900031 - Freie Schlagwörter (DE)
- Azomethin-Yliden, Cycloaddition, Heterozyklen, polyzyklische aromatische Kohlenwasserstoffe, radikalische Kationen
- Freie Schlagwörter (EN)
- azomethine ylides, cycloaddition, heterocycles, polycyclic aromatic hydrocarbons, radical cations
- Klassifikation (DDC)
- 540
- Verlag
- Wiley-VCH, Weinheim
- Förder- / Projektangaben
- European Commission
Horizon2020
GrapheneCore1ID: 696656
Deutsche ForschungsgemeinschaftCenter for Advancing Elektronics Dresden (cfaed)
ID: 194636624
Deutsche Forschungsgemeinschaft EnhanceNanoID: 391979941
European Social FundGRAPHD - Version / Begutachtungsstatus
- angenommene Version / Postprint / Autorenversion
- URN Qucosa
- urn:nbn:de:bsz:14-qucosa2-731404
- Veröffentlichungsdatum Qucosa
- 14.12.2020
- Dokumenttyp
- Artikel
- Sprache des Dokumentes
- Englisch
- Lizenz / Rechtehinweis