9‐Boraanthracene Derivatives Stabilized by N‐Heterocyclic Carbenes

Abstract

2009: A boraanthracene odyssey: General routes to boraanthracene derivatives--long proposed, but never observed--are disclosed, along with the structural and photophysical properties of these compounds and their remarkable reactivity towards oxygen.

N‐Heterocyclic Carbene Boranes as Electron‐Donating and Electron‐Accepting Components of π‐Conjugated Systems

“…[10] However, studies of NHC-boranes from a materials point of view have been limited to only a few examples. [11] An unsaturated NHC-bearing borabenzene with a coplanar geometry was also reported by Herberich and co-workers, in which, however, the borabenzene and the NHC ring are not noticeably conjugated to each other as a result of their different electronic characters. [11] An unsaturated NHC-bearing borabenzene with a coplanar geometry was also reported by Herberich and co-workers, in which, however, the borabenzene and the NHC ring are not noticeably conjugated to each other as a result of their different electronic characters.…”

Benzo‐ and Naphthoborepins: Blue‐Emitting Boron Analogues of Higher Acenes

“…[7] For the latter reason, those borepins that are known tend to be annulated by other rings, [8] which provides a stabilizing influence on the borepin core structure. [9] We have been interested in boron-containing analogues of higher acenes, [10] given the utility of the all-carbon species in organic semiconductor applications.…”

N‐Heterocyclic Carbene Stabilized Boryl Radicals

“…It is obvious that, to av ariable extent, similar mesomeric structures must also be considered for the radicals 1-7 (vide infra). [44,45] Thea ccessibility of reduced radical species from the borenium ions 10 was studied electrochemically.F igure 3 shows the cyclic voltammograms of 10 a-c (Figure 3), which display quasi-reversible one-electron-reduction waves at potentials of E 1/2 = À2.02 V( 10 a), À2.12 V( 10 b), and À1.56 V( 10 c)v ersus the ferrocene/ferrocenium redox couple (Fc/Fc + ). Therefore,the pair 8/ Me 3 SiOTf and related systems were termed frustrated Nheterocyclic carbene/silylium ion Lewis pairs.…”