From a 1,2-azaborinine to largeBN-PAHsviaelectrophilic cyclization: synthesis, characterization and promising optical properties

Abstract

A synthetic approach towards boron-nitrogen substituted polycyclic aromatic hydrocarbons (BN-PAHs) via electrophilic cyclization is described and it is shown that the variation of the rings' connectivity may tune the emission wavelengths effectively.

One tool to bring them all: Au-catalyzed synthesis of B,O- and B,N-doped PAHs from boronic and borinic acids

“…This promotes a coplanar conformation between the respective B,O heterocycle and, e.g., B-bonded phenyl substituents and can thus contribute to the increase of conjugation lengths and the extension of the frontier orbitals from the oxaborin moiety to the phenyl ring. 38,47,52,[58][59][60] If one proceeds further from B,E-PAHs to (B,E)n-PAHs with E = N or O and n > 1, the available information again becomes dramatically less, 9,11,13,30,32,39,54,55,[61][62][63][64][65][66][67][68][69][70][71][72][73][74][75][76][77][78] which is unfortunate, because some evidence has already been gathered that the number n of embedded -B=E + units significantly influences the chemical and physical properties of corresponding compounds. 30,54,68,72,79 Thus, new atom-economic strategies for the construction of (B,E)n-PAHs, which ideally avoid the use of sensitive boron halides, sophisticated organometallic reagents, or forcing reaction conditions, are still in demand.…”

BN-Substituted coronene diimide donor–acceptor–donor triads: photophysical, (spectro)-electrochemical studies and Lewis behavior

“…27- 30 The second method is based on transition metal-catalyzed cycloisomerization of ethynyl groups after the BN-bond has been already formed using platinium [31][32][33] or gold catalyst. 34 A third, less common method to access BN-PAHs is the use of ring-closing metathesis reactions, 35, 36 which originated from the synthesis of substituted 1,2-azaborines.…”

“…pyrene, 38, 39 perylene 34 or acenes. 33,40 The implementation of BN units into structures that are already inherently electron-deficient, such as BN-substituted perylene diimide (Ph-BNPDI), 41 remains rare so far. Carbon-based Donor (D) and acceptor (A) substituted conjugated compounds have been widely used for organic electronics, 42, 43 two-photon absorption, 44 and non-linear optics.…”

Stimuli‐Responsive Polycycles Based on Hetero‐Buckybowl Trithiasumanene

“…Polycyclic aromatic hydrocarbons (PAHs) are key building blocks for organic luminescent, [ 10 ] electrical, [ 11 ] and photovoltaic materials. [ 12 ] Recently, the non‐planar PAHs have drawn intensive attention owing to their unique physical and chemical properties.…”