Richter, Marcus
[Author];
Schellhammer, Karl Sebastian
[Author];
Machata, Peter
[Author];
Cuniberti, Gianaurelio
[Author];
Popov, Alexey
[Author];
Ortmann, Frank
[Author];
Berger, Reinhard
[Author];
Müllen, Klaus
[Author];
Feng, Xinliang
[Author]
Polycyclic heteroaromatic hydrocarbons containing a benzoisoindole core
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Media type:
E-Article
Title:
Polycyclic heteroaromatic hydrocarbons containing a benzoisoindole core
Contributor:
Richter, Marcus
[Author];
Schellhammer, Karl Sebastian
[Author];
Machata, Peter
[Author];
Cuniberti, Gianaurelio
[Author];
Popov, Alexey
[Author];
Ortmann, Frank
[Author];
Berger, Reinhard
[Author];
Müllen, Klaus
[Author];
Feng, Xinliang
[Author]
Published:
Cambridge: Royal Society of Chemistry, [2020]
Published in:Organic Chemistry Frontiers ; 4,5 (2017), Seite 847-852
Description:
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.