Three fluorinated BsubPcs have been synthesized and characterized. Crystals suitable for XRD were grown by slow vapor diffusion and sublimation. Analysis of their crystal structures revealed a dimeric association of BsubPc units for F 5 BsubPc and columnar packing for F 12 BsubPc and F 17 BsubPc. Cyclic volatmmetry (CV) was used to probe the frontier orbital energy levels of these compounds in both dichloromethane and acetonitrile solution; however, only F 5 BsubPc underwent oxidative events, whereas all three compounds underwent reductive events. A -362 and -37 mV shift in the reductive peak potential was observed for peripheral and axial fluorination, respectively, as measured by cyclic voltammetry. Solution UV-vis absorption and photoluminescence spectra were measured in dichloromethane. All three compounds demonstrated air-stable n-type conductivity in single-carrier devices and extremely narrow orange EL emission with a fwhm of only ∼30 nm. F 5 BsubPc showed a maximum luminescence of 122 cd/m 2 at 8 V, with a maximum current efficiency of 0.03 cd/A, whereas the devices fabricated from F 12 BsubPc and F 17 BsubPc produced luminescence with a maximum value of <1 cd/m 2 .
In the title compound, C31H7BF12N6O, molecules are arranged into one-dimensional columns with an intermolecular B⋯B distance of 5.3176 (8) Å. Bowl-shaped molecules are arranged within the columns in a concave bowl-to-ligand arrangement separated by a ring centroid distance of 3.532 (2) Å between the benzene ring of the 4-methylphenoxy ligand and one of the three five-membered rings of a symmetry-related molecule.
The title compound, C24BBrF12N6 or Br-F12BsubPc (BsubPc is boronsubphtalocyanine), has a bowl-shaped structure with an approximate molecular C
3v symmetry characteristic of boronsubphthalocyanine compounds. In the crystal, molecules are arranged in one-dimensional columns and the boron–subphthalocyanine units within each column are offset and angled in a bowl-to-ligand packing arrangement such that the axial Br atom rests in the aromatic concaved bowl of the neighboring subphthalocyanine with an intermolecular Br⋯B distance of 3.721 (3) Å.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.