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The incorporation of heteroatoms into hydrocarbon compounds greatly expands the chemical space of molecular materials. In this context, B−N doping takes a center stage due to its isosterism with a C=C‐bond. Herein, we present a new and modular synthetic concept to access novel diazadiborabenzo[b]triphenylenes 7 a–h using the B−N doped biradical 16 as intermediate. Characterization of the photophysical properties revealed the emission spectra of the diazadibora benzo[b]triphenylenes 7 a–h can conveniently be tuned by small changes of the substitution on the boron‐atom. All of the diazadibora compounds show a short life‐time phosphorescence. Additionally, we were able to rationalize the excited‐state relaxation of the diazadiboraacene 7 a via intersystem crossing by quantum chemical calculations. The new synthetic strategy provides an elegant route to various novel B−N doped acenes with great potential for applications in molecular materials. [ABSTRACT FROM AUTHOR]

Triarylboranes containing linear or angular benzodithiophene moieties and bearing one or two dimesitylboron units were synthesized. The electrochemical and optical features of these compounds were investigated by cyclic voltammetry, UV/Vis and fluorescence spectroscopy while DFT calculations were run to analyze the energetic landscape of these systems. For both linear and angular benzodithiophenes, symmetrical disubstitution leads to the highest photoluminescence yields. The linear benzodithiophene disubstituted with two dimesitylboron units proved to be the most interesting and promising molecule as an electron‐transport material for organic electronics owing to its LUMO energy level of −2.84 eV which is close to those of commonly used electron transport materials like bathocuproine or bathophenantroline. [ABSTRACT FROM AUTHOR]