Publication details for Professor Andy MonkmanKotwica, Kamil, Bujak, Piotr, Data, Przemyslaw, Krzywiec, Wojciech, Wamil, Damian, Gunka, Piotr A., Skorka, Lukasz, Jaroch, Tomasz, Nowakowski, Robert, Pron, Adam & Monkman, Andrew (2016). Soluble Flavanthrone Derivatives: Synthesis, Characterization, and Application to Organic Light-Emitting Diodes. Chemistry - A European Journal 22(23): 7978-7986.
- Publication type: Journal Article
- ISSN/ISBN: 0947-6539 (print), 1521-3765 (online)
- DOI: 10.1002/chem.201600513
- Further publication details on publisher web site
- Durham Research Online (DRO) - may include full text
Author(s) from Durham
Simple modification of benzo[h]benz[5,6]acridino[2,1,9,8-klmna]acridine-8,16-dione, an old and almost-forgotten vat dye, by reduction of its carbonyl groups and subsequent O-alkylation, yields solution-processable, electroactive, conjugated compounds of the periazaacene type, suitable for the use in organic electronics. Their electrochemically determined ionization potential and electron affinity of about 5.2 and −3.2 eV, respectively, are essentially independent of the length of the alkoxyl substituent and in good agreement with DFT calculations. The crystal structure of 8,16-dioctyloxybenzo[h]benz[5,6]acridino[2,1,9,8-klmna]acridine (FC-8), the most promising compound, was solved. It crystallizes in space group Pmath formula and forms π-stacked columns held together in the 3D structure by dispersion forces, mainly between interdigitated alkyl chains. Molecules of FC-8 have a strong tendency to self-organize in monolayers deposited on a highly oriented pyrolytic graphite surface, as observed by STM. 8,16-Dialkoxybenzo[h]benz[5,6]acridino[2,1,9,8-klmna]acridines are highly luminescent, and all have photoluminescence quantum yields of about 80 %. They show efficient electroluminescence, and can be used as guest molecules with a 4,4′-bis(N-carbazolyl)-1,1′-biphenyl host in guest/host-type organic light-emitting diodes. The best fabricated diodes showed a luminance of about 1900 cd m−12, a luminance efficiency of about 3 cd A−1, and external quantum efficiencies exceeding 0.9 %.