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Polycyclic Aromatic Hydrocarbons Containing A Pyrrolopyridazine Core
Author(s) -
Richter Marcus,
Fu Yubin,
Dmitrieva Evgenia,
Weigand Jan J.,
Popov Alexey,
Berger Reinhard,
Liu Junzhi,
Feng Xinliang
Publication year - 2019
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201900031
Subject(s) - chemistry , density functional theory , cyclic voltammetry , spectroscopy , solvent , absorption spectroscopy , photochemistry , mass spectrometry , fluorescence spectroscopy , electron paramagnetic resonance , polycyclic aromatic hydrocarbon , nuclear magnetic resonance spectroscopy , fluorescence , computational chemistry , organic chemistry , electrochemistry , nuclear magnetic resonance , physics , electrode , quantum mechanics , chromatography
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 .