13214-70-5Relevant articles and documents
Synthesis of substituted dibenz[a,c]anthracenes and an investigation of their liquid-crystalline properties
Psutka, Katie M.,Williams, Joshua,Paquette, Joseph A.,Calderon, Oliver,Bozek, Kevin J.A.,Williams, Vance E.,Maly, Kenneth E.
, p. 1456 - 1463 (2015)
We report the synthesis of a series of 2,3,5,6-tetraalkoxydibenz[ a,c]anthracenes bearing substituents (H, OCH3, or CN) in the 11- and 12-positions and an investigation of their liquid- crystalline properties. The synthesis involved Suzuki coupling of the appropriate dibromonaphthalene and boronate ester, followed by an oxidative cyclization. Compounds 4 and 5, bearing OCH3 and H, respectively, do not exhibit any liquid-crystalline properties. In contrast, compounds 6a-c, bearing cyano groups, assemble into columnar mesophases, suggesting that electron-withdrawing groups are important for promoting columnar mesophase assembly. Analysis of the XRD revealed that compound 6b exhibits a columnar hexagonal phase, whereas compounds 6a and 6c exhibit columnar rectangular phases. The XRD data of 6a and 6b also show reflections that are consistent with antiparallel dimers within the columnar stacks, and intercolumnar spacings suggest that molecules are tilted within the columns.
Selective Vicinal Diiodination of Polycyclic Aromatic Hydrocarbons
Bolte, Michael,Jin, Tao,John, Alexandra,Kaehler, Tanja,Lerner, Hans-Wolfram,Wagner, Matthias
supporting information, p. 5847 - 5851 (2020/09/09)
Vicinally diiodinated polycyclic aromatic hydrocarbons (I2-PAHs) are accessible from the corresponding diborylated B2-PAHs through boron/iodine exchange. The B2-PAHs have been prepared via twofold electrophilic borylation reactions templated by a vicinally disilylated benzene. Our protocol is applicable to fluorenes, acenes, annulated acenes, oligoaryls, and even [5]helicene. Using B2-naphthalene as the example, we have shown that the reaction scope can, in principle, be expanded to include the synthesis of vicinally dibrominated and dihydroxylated PAHs. The usefulness of the building blocks provided by our method in the field of optoelectronic materials was demonstrated by the successful conversion of I2-fluoranthene to the analogous doubly alkynylated fluoranthene emitter.
How Boron Doping Shapes the Optoelectronic Properties of Canonical and Phenylene-Containing Oligoacenes: A Combined Experimental and Theoretical Investigation
Kirschner, Sven,Mewes, Jan-Michael,Bolte, Michael,Lerner, Hans-Wolfram,Dreuw, Andreas,Wagner, Matthias
supporting information, p. 5104 - 5116 (2017/04/18)
Optimized syntheses of 6,13-dimesityl-6,13-dihydro-6,13-diborapentacene (DBP) and a related compound (DBI) featuring two biphenylene-2,3-diyl units in place of naphthalene-2,3-diyl moieties are reported. Striking differences between the optoelectronic properties of DBP and DBI have been experimentally observed, and explained by quantum chemical calculations. DBP is a member of the oligoacene family, DBI is a linear [N]phenylene derivative. The yellow DBP shows blue photoluminescence, the deep red DBI is nonfluorescent. Both compounds give rise to two reversible redox transitions at E12 =?2.03 V, ?2.75 V (DBP) and ?1.52 V, ?2.30 V (DBI; THF, vs. FcH/FcH+). The higher electron affinity of DBI agrees with a lower calculated LUMO energy level [?0.57 eV for DBI with respect to DBP @HF//SCS-MP2/def2-TZVP] and a higher Lewis acidity of its boron centers, which is reflected in the trend of adduct formation with small Lewis bases (MeCN, F?). The thermochemistry underlying this trend, as well as the mechanism of fluorescence quenching in DBI, are revealed by state-of-the-art quantum chemical calculations. It is suggested that the nonradiative deactivation occurs via a low-lying, doubly excited state.
MULTICYCLIC AROMATIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE USING THE SAME
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Paragraph 0155; 0158-0159, (2017/04/21)
The present specification describes a multicyclic aromatic ring compound having a novel structure and an organic light emitting device using the same.
