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Issue 5, 2017
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Polycyclic heteroaromatic hydrocarbons containing a benzoisoindole core

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Abstract

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.

Graphical abstract: Polycyclic heteroaromatic hydrocarbons containing a benzoisoindole core

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Article information


Submitted
06 Mar 2017
Accepted
31 Mar 2017
First published
04 Apr 2017

Org. Chem. Front., 2017,4, 847-852
Article type
Research Article

Polycyclic heteroaromatic hydrocarbons containing a benzoisoindole core

M. Richter, K. S. Schellhammer, P. Machata, G. Cuniberti, A. Popov, F. Ortmann, R. Berger, K. Müllen and X. Feng, Org. Chem. Front., 2017, 4, 847
DOI: 10.1039/C7QO00180K

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