Polycyclic Aromatic Hydrocarbons Containing A Pyrrolopyridazine Core

Richter M, Fu Y, Dmitrieva E, Weigand JJ, Popov A, Berger R, Liu J, Feng X (2019)

Publication Type: Journal article

Publication year: 2019

Journal

ChemPlusChem Wiley

Book Volume: 84

Pages Range: 613-618

Journal Issue: 6

DOI: 10.1002/cplu.201900031

Abstract

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.

Involved external institutions

Technische Universität Dresden DE Germany (DE) Leibniz-Institut für Festkörper- und Werkstoffforschung Dresden e.V. (IFW) / Leibniz Institute for Solid State and Materials Research Dresden DE Germany (DE)

How to cite

APA:

Richter, M., Fu, Y., Dmitrieva, E., Weigand, J.J., Popov, A., Berger, R.,... Feng, X. (2019). Polycyclic Aromatic Hydrocarbons Containing A Pyrrolopyridazine Core. ChemPlusChem, 84(6), 613-618. https://doi.org/10.1002/cplu.201900031

MLA:

Richter, Marcus, et al. "Polycyclic Aromatic Hydrocarbons Containing A Pyrrolopyridazine Core." ChemPlusChem 84.6 (2019): 613-618.

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