Issue 5, 2017

Polycyclic heteroaromatic hydrocarbons containing a benzoisoindole core

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

Supplementary files

Article information

Article type
Research Article
Submitted
06 Marts 2017
Accepted
31 Marts 2017
First published
04 Apr. 2017

Org. Chem. Front., 2017,4, 847-852

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements