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.
| Identifer | oai:union.ndltd.org:DRESDEN/oai:qucosa:de:qucosa:36567 |
| Date | 31 January 2020 |
| Creators | Richter, Marcus, Schellhammer, Karl Sebastian, Machata, Peter, Cuniberti, Gianaurelio, Popov, Alexey, Ortmann, Frank, Berger, Reinhard, Müllen, Klaus, Feng, Xinliang |
| Publisher | Royal Society of Chemistry |
| Source Sets | Hochschulschriftenserver (HSSS) der SLUB Dresden |
| Language | English |
| Detected Language | English |
| Type | info:eu-repo/semantics/acceptedVersion, doc-type:article, info:eu-repo/semantics/article, doc-type:Text |
| Rights | info:eu-repo/semantics/openAccess |
| Relation | 2052-4129, 10.1039/C7QO00180K, 10.1039/C7QO00180K, info:eu-repo/grantAgreement/Europäischer Sozialfonds/Horizon2020/100270084//Graphenzentrum Dresden/GraphD |
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