Influence of the Bridging Elements on the Optical Properties of Linked 9,10-Dihydro-9,10-diboraanthracenes

Abstract

Starting from the monofunctionalized 9,10dihydro-9,10-diboraanthracene derivatives MesB(C 6 H 4 ) 2 BX (X = H, Br), the bridged systems MesB(C 6 H 4 ) 2 B−L− B(C 6 H 4 ) 2 BMes have been synthesized with L = −C(H) C(H)(p-C 6 Me 4 )C(H)C(H)− (5), −CC(p-C 6 Me 4 )C C− (6), and −(p-C 6 H 4 )(p-C 6 Me 4 )(p-C 6 H 4 )− ( 7). The compounds were characterized by NMR, IR, UV/vis, and fluorescence spectroscopy. The vinyl-and phenylboranes 5 and 7 are pale yellow solids, whereas the alkynylborane 6 possesses a bright yellow color. The emission maxima of 5−7 in toluene are λ max (em) 477, 460, and 461 nm with quantum yields ϕ f of 0.02, 0.30, and 0.04, respectively. Alkynylborane 6 was found to be the least air-and moisture-sensitive of the three derivatives.

How Boron Doping Shapes the Optoelectronic Properties of Canonical and Phenylene‐Containing Oligoacenes: A Combined Experimental and Theoretical Investigation

“…Moreover, the redox activity of compounds 1 renders them potential building blocks for n‐type semiconductors. Due to the fact that properly modified 9,10‐dihydro‐9,10‐diboraanthracenes show strong photoluminescence, they are also being investigated as candidate materials for organic light‐emitting devices (OLEDs) …”

“…Due to the fact that properly modified 9,10-dihydro-9,10-diboraanthracenes shows trong photoluminescence, they are also being investigateda sc andidate materials for organic light-emittingdevices (OLEDs). [10][11][12] The substituents Ra nd R' provide useful set-screwst ot ailor the propertieso f1 for ag iven purpose. The parent compound (R = R' = H) can readily be derivatizedthrough hydroboration reactions to furnish brightly luminescent, yet air-and moisturesensitiveproducts.…”

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

“…25 In particular, we are developing derivatives of 9,10-dihydro-9,10-diboraanthracene (DBA), [26][27][28][29][30] which possess outstanding optoelectronic properties. 28,[31][32][33] A challenge generally encountered with organoboranes is their sensitivity towards air and moisture. Common solutions of this problem are stabilisation of the molecules by (i) sterically demanding substituents 34 or (ii) incorporation of the boron atom into a rigid, planar framework.…”

Boron, aluminium, gallium, indium and thallium

“…145 Other novel polyaromatic hydrocarbons containing boron reported in 2012 included diarene-fused 1,2-dihydro-1,2-diborins (in both neutral and dianionic forms), 146 pentacyclic acenes containing two formally aromatic borepin rings 147 and a range of 9,10-dihydro-9,10-diboraanthracene based compounds. 148,149 The latter exhibited large Stokes shifts and bright fluorescence due to the suppression of p-p interactions. 1,2-C 6 H 4 (BH 2 ÁSMe 2 ) 2 was demonstrated to condense to the SMe 2 diadduct of 9,10-dihydro-9,10-diboraanthracene.…”