Selective access to either a doubly boron-doped tetrabenzopentacene or an oxadiborepin from the same precursor

Abstract

Depending on the solvent, a brominated arylborane gave the multiple helicene B2-TBPA (pyridine) or the oxadiborepin ODBE (THF) after intramolecular Yamamoto coupling.

Doubly Boron‐Doped TADF Emitters Decorated with ortho‐Donor Groups for Highly Efficient Green to Red OLEDs

“…Meanwhile, the two boron atoms in the DBA moiety possess a trigonal planar geometry (Σ(C‐B‐C) = 360°). The exocyclic B(1)−C(18) bond lengths of 1.585(3) Å for 2 and 1.587(2) Å for 4 are in a similar range to those observed for Ar 2 DBA compounds (B−C Ar , 1.57–1.61 Å), [6c, 7, 8a, d, f, 12] as well as for usual triarylboranes such as BPh 3 and BMes 3 (1.57–1.59 Å) [13] . However, the B−C endo (DBA) bond lengths (ca.…”

Dithiophene‐Fused Oxadiborepins and Azadiborepins: A New Class of Highly Fluorescent Heteroaromatics

“…The unexpected product C formed through hydrolysis during the workup procedure. Only few further examples of compounds featuring oxadiborepin as a substructure have been reported in the literature [17–20] . The first one, described by Wagner and co‐workers in 2011, was a bisboronic acid anhydride [17] .…”

“…The first one, described by Wagner and co‐workers in 2011, was a bisboronic acid anhydride [17] . Recently, they presented the BOB‐doped PAH I [18] . Due to steric congestion between the annulated benzene rings, this species deviates significantly from planarity.…”

Heteroelement Analogues of Benzoxaborole and Related Ring Expanded Systems

“…However, unlike benzoxadiboroles, the B-O-B linkage in 32 seems to be rather stable as there are no data which might indicate that a reversible hydrolysis to naphthalene-1,8-diboronic acid occurs to any appreciable extent. Compound 32 was used as a starting material for synthesis of a few 1H,3H-naphth[l,8-cd][l,2,6]oxadiborin derivatives (34)(35)(36)(37) where hydroxyl groups were replaced with OMe, Cl, Me [23], or mesityl (Mes) substituents [24], respectively. Very recently, a structurally extended analogue of 32 based on bicyclohexene-perinaphthalene framework 38 was obtained using an analogous protocol involving brominelithium exchange in an appropriate dibromide, followed by boronation.…”