Untersuchungen über Indanthren und Flavanthren. II

Schöll, Roland; Berblinger, H.

doi:10.1002/cber.190303603130

Cited by 16 publications

(2 citation statements)

References 8 publications

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“…Inversion-related molecules form dimers through p stacking accompanied by CÀH···Oi nteractions (Figure 7, d(C29···O2 i ) = 3.332(4) , d(H29B···O2 i ) = 2.44 , C29-H29B···O2 = 1508, i = 1Àx, Figure S2 in the Supporting Information). The distance between meanp lanes of the aromatic cores in the dimers is 3.4398(11) w ith ap lane shift of 1.7825 (12) , while the interplanar distance between molecules from the adjacent dimers is 3.3030 (15) , but the plane shift is 7.8503(14) ( Figure S2 in the SupportingI nformation).C olumns are held togetheri nt he 3D structure by dispersion forces, mainly between interdigitated alkyl chains. In this crystalline arrangement it is possible to identify almost flata nd denselyp acked slices of molecules with 2D ordering very similar to that found in the monolayer depositedo nH OPG (Figure S3 in Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

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Soluble Flavanthrone Derivatives: Synthesis, Characterization, and Application to Organic Light‐Emitting Diodes

Kotwica

Bujak

Data

et al. 2016

Chemistry A European J

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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 P1‾ 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 %.

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Section: Resultsmentioning

confidence: 99%

“…The synthesis of flavanthrone has been known for over 100 years; however, it had to be modified to meet the standards of modern organic chemistry and to improve the reaction yield. Flavanthrone is also commercially available, but requires additional purification when used for the preparation of new semiconductors.…”

Section: Resultsmentioning

confidence: 99%