7136-57-4Relevant academic research and scientific papers
2,7-substituted hexafluoroheterofluorenes as potential building blocks for electron transporting materials
Geramita, Katharine,McBee, Jennifer,Tilley, T.Don
supporting information; experimental part, p. 820 - 829 (2009/06/20)
A series of 2,7-substituted hexafluoro-9-heterofluorenes was synthesized via nucleophilic aromatic substitution (SNArN) reactions of phenyllithium, thienyllithium, and lithium phenylacetylide with various octafluoroheterofluorenes and 2,2'-dibromooctafluorobiphenyl. These compounds are of interest as possible building blocks for materials with useful electron transport properties, since they possess relatively low LUMO energy levels. The HOMO-LUMO energy gaps, as determined by UV-vis spectroscopy, range between 3.0 and 3.9 eV, while photoluminescence emission spectra reveal λ ems values in the range of 365 to 420 nm (corresponding to ultraviolet to violet/blue emission). Dilute solution state quantum yields vary significantly with the nature of the heteroatom and the 2,7-substituents, and approach unity for a number of the di(phenylethynyl) derivatives. The experimentally determined LUMO energy levels (- 2.7 to - 3.3 eV as determined by differential pulse voltammetry) suggest that these compounds may be good candidates for electron transport applications. Single-crystal X-ray analyses of a number of compounds revealed cofacial packing in all cases, with intermolecular distances as short as 3.4 A.
F8BINOL, an electronically perturbed version of BINOL with remarkable configurational stability
Yudin, Andrei K.,Martyn, L. James P.,Pandiaraju, Subramanian,Zheng, Juan,Lough, Alan
, p. 41 - 44 (2007/10/03)
(formula presented) Substitution of hydrogens by fluorines at the 5, 5′, 6, 6′, 7, 7′, 8, and 8′ positions of BINOL strongly affects distribution of electron density within the biaryl skeleton but has a very small influence on the torsion angle. The most
THE CRYSTAL AND MOLECULAR STRUCTURE OF OCTAFLUORODIBENZOTHIOPHENE
Jones, J. Bowen,Brown, D. S.,Massey, A. G.
, p. 67 - 70 (2007/10/02)
The X-ray crystal structure of octafluorodibenzothiophene is reported.Despite the larger size of fluorine relative to hydrogen there is surprisingly little change in molecular dimensions when the hydrogen atoms of dibenzothiophene are replaced by fluorine.The 3 and 3' fluorine atoms are closer together (2.549 Angstroem) than the sum of the accepted van der Waals radii.Dibenzothiophene and octafluorodibenzothiophene form a 1:1 crystalline ''complex''.
