NDLI: Effects of boron doping on the structural and optoelectronic properties of 9,10-diarylanthracenes

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Bolte, Michael Januszewski, Estera Diefenbach, Martin Lerner, Hans-wolfram Holthausen, Max C. Hoffend, Claas Wagner, Matthias
Description	Author Affiliation: Hoffend C ( Institut für Anorganische Chemie, J.W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, D-60438 Frankfurt (Main), Germany. Matthias.Wagner@chemie.uni-frankfurt.de.)
Abstract	Key structural and optoelectronic properties of 9,10-dihydro-9,10-diboraanthracene (DBA) derivatives carrying mesityl (2a), 2-methylnaphthyl- (2b) and 9-phenyl-2,7-di-tert-butylanthryl (2c) substituents at the boron atoms have systematically been compared with the properties of their all-carbon congeners 4a–c. The experimental investigations have been augmented by quantum-chemical calculations. Steric repulsion leads to large dihedral angles between the aryl substituents and the DBA (2a–c) or anthrylene (4a–c) cores; as a result, the B–C bonds of 2a–c are kinetically shielded from hydrolysis and oxidative degradation. Lithium metal reduces the mesityl derivative 2a to the inverse sandwich complexes $[Li(OR_{2})_{n}]_{2}[2a]$ (X-ray crystallography; $OR_{2}$ = THF, n = 2; $Et_{2}O,$ n = 1). In line with the nodal structures of the LUMO of 2a/HOMO of $[Li(THF)_{2}]_{2}[2a],$ the C–C bond lengths of the anionic fragment $[2a]^{2−}$ show characteristic differences to those of 2a and come close to the C–C bond lengths of the isoelectronic species 4a. X-ray crystallography on anti-2b × 2 $C_{6}H_{6}$ and anti-4b × 2 $C_{6}H_{6}$ reveals an essentially identical packing of the main molecules. The benzene solvate molecules, however, interact in a very different manner with anti-2b or anti-4b, which can be traced down to subtle disparities between the electron density distributions of the two compounds. 2a–c undergo a photoinduced aryl-to-DBA charge transfer; the back electron transfer results in blue (2a), green (2b) and red (2c) emission, albeit with low quantum yields. 4a–c are characterised by a local π–π* photoexcitation of the central 9,10-anthrylene fragments and corresponding blue emission. Each of the compounds 2a–c gives rise to two reversible DBA-centred one-electron transitions in the cyclic voltammogram.
ISSN	14779226
Issue Number	38
Journal	Dalton Trans.
Volume Number	42
e-ISSN	13645447
Language	English
Publisher	Royal Society of Chemistry
Publisher Date	2013-10-14
Publisher Place	Great Britain (UK)
Access Restriction	Subscribed
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Inorganic Chemistry

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