Polycyclic heteroaromatic hydrocarbons containing a benzoisoindole core

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Titel: Polycyclic heteroaromatic hydrocarbons containing a benzoisoindole core

Beteiligte: Richter, Marcus [Verfasser:in]; Schellhammer, Karl Sebastian [Verfasser:in]; Machata, Peter [Verfasser:in]; Cuniberti, Gianaurelio [Verfasser:in]; Popov, Alexey [Verfasser:in]; Ortmann, Frank [Verfasser:in]; Berger, Reinhard [Verfasser:in]; Müllen, Klaus [Verfasser:in]; Feng, Xinliang [Verfasser:in]

Erschienen: Cambridge: Royal Society of Chemistry, [2020]

Sprache: Englisch

DOI: 10.1039/C7QO00180K; 10.1039/C7QO00180K

Schlagwörter: Polycyclische Kohlenwasserstoffe ; Polycyclic hydrocarbons ; azaphenalene ; Azaphenalene

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Beschreibung: By the combination of 9a-azaphenalene and a perpendicularly oriented acene, we have synthesized three derivatives of a series of novel, fully-conjugated nitrogen-containing polycyclic aromatic hydrocarbons (PAHs), namely [7,8]naphtho[2′,3′:1,2]indolizino[6,5,4,3-def]phenanthridine, with an acetylene triisopropylsilyl (TIPS), phenyl or benzothiophenyl substituent. Their optoelectronic properties were studied via UV-Vis-NIR absorption, fluorescence spectroscopy and cyclic voltammetry. In addition, in situ spectroelectrochemistry was performed to investigate the optical and magnetic properties of the mono-radical cation and anion by quasi-reversible oxidation and reduction of 11-(tert-butyl)-5,17-bis((triisopropylsilyl)ethynyl)[7,8]naphtho[2′,3′:1,2]indolizino[6,5,4,3-def]phenanthridine (1a). Theoretical modelling confirmed the predominately closed-shell electronic ground state with a weak diradical character depending on the geometry.

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