Polycyclic Aromatic Hydrocarbons Containing A Pyrrolopyridazine Core. - National Genomics Data Center (CNCB-NGDC)

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Polycyclic Aromatic Hydrocarbons Containing A Pyrrolopyridazine Core.

Marcus Richter, Yubin Fu, Evgenia Dmitrieva, Jan J Weigand, Alexey Popov, Reinhard Berger, Junzhi Liu, Xinliang Feng

Author Information

Marcus Richter: Dresden University of Technology, Center for Advancing Electronics Dresden (cfaed), Faculty of Chemistry and Food Chemistry, Institute for Molecular Functional Materials, Mommsenstraße 4, 01069, Dresden, Germany. ORCID
Yubin Fu: Dresden University of Technology, Center for Advancing Electronics Dresden (cfaed), Faculty of Chemistry and Food Chemistry, Institute for Molecular Functional Materials, Mommsenstraße 4, 01069, Dresden, Germany. ORCID
Evgenia Dmitrieva: Leibniz Institute for Solid State and Materials Research, Nanoscale Chemistry, Center of Spectroelectrochemistry, Helmholtzstrasse 20, 01069, Dresden, Germany.
Jan J Weigand: Dresden University of Technology, Faculty of Chemistry and Food Chemistry, Institute of Inorganic Molecular Chemistry, Mommsenstraße 4, 01069, Dresden, Germany. ORCID
Alexey Popov: Leibniz Institute for Solid State and Materials Research, Nanoscale Chemistry, Center of Spectroelectrochemistry, Helmholtzstrasse 20, 01069, Dresden, Germany. ORCID
Reinhard Berger: Dresden University of Technology, Center for Advancing Electronics Dresden (cfaed), Faculty of Chemistry and Food Chemistry, Institute for Molecular Functional Materials, Mommsenstraße 4, 01069, Dresden, Germany. ORCID
Junzhi Liu: Dresden University of Technology, Center for Advancing Electronics Dresden (cfaed), Faculty of Chemistry and Food Chemistry, Institute for Molecular Functional Materials, Mommsenstraße 4, 01069, Dresden, Germany. ORCID
Xinliang Feng: Dresden University of Technology, Center for Advancing Electronics Dresden (cfaed), Faculty of Chemistry and Food Chemistry, Institute for Molecular Functional Materials, Mommsenstraße 4, 01069, Dresden, Germany. ORCID

PMID: 31944030 DOI: 10.1002/cplu.201900031

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.

azomethine ylides cycloaddition heterocycles polycyclic aromatic hydrocarbons radical cations

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