(Dimesityl)boron Benzodithiophenes: Synthesis, Electrochemical, Photophysical and Theoretical Characterization

Abstract

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 disubstitu-tion 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 À 2.84 eV which is close to those of commonly used electron transport materials like bathocuproine or bathophenantroline.

(BO)2‐Doped Tetrathia[7]helicene: A Configurationally Stable Blue Emitter

“…E was chosen as the “host scaffold” for BO incorporation, because the considerable application potential of thiophene‐containing organic compounds is recognized in various fields, such as non‐linear optical (NLO) materials, [14] electroactive materials, [15] light‐emitting devices (OLEDs), [16] and thin‐film transistors (TFTs). [ 17 , 18 ] Moreover, the facile functionalization of the α positions of the thiophene ring is a valuable asset during synthesis, e.g ., when it comes to late‐stage bromination reactions of BO‐doped synthesis intermediates (see Scheme 1 ). The chiral resolution of rac ‐ 1 was achieved, and the enantiomerization barrier as well as important chiroptical properties of the individual enantiomers were determined in a combined experimental and theoretical effort.…”

(BO)2‐Doped Tetrathia[7]helicene: A Configurationally Stable Blue Emitter

“…Herein, we report double B(sp 2 )−O doping of tetrathia[7]helicene E [12, 13] to generate 1 (Figure 1). E was chosen as the “host scaffold” for BO incorporation, because the considerable application potential of thiophene‐containing organic compounds is recognized in various fields, such as non‐linear optical (NLO) materials, [14] electroactive materials, [15] light‐emitting devices (OLEDs), [16] and thin‐film transistors (TFTs) [17, 18] . Moreover, the facile functionalization of the α positions of the thiophene ring is a valuable asset during synthesis, e.g ., when it comes to late‐stage bromination reactions of BO‐doped synthesis intermediates (see Scheme 1).…”

“…E was chosen as the "host scaffold" for BO incorporation, because the considerable application potential of thiophene-containing organic compounds is recognized in various fields, such as non-linear optical (NLO) materials, [14] electroactive materials, [15] light-emitting devices (OLEDs), [16] and thinfilm transistors (TFTs). [17,18] Moreover, the facile functionalization of the α positions of the thiophene ring is a valuable asset during synthesis, e.g., when it comes to late-stage bromination reactions of BO-doped synthesis intermediates (see Scheme 1). The chiral resolution of rac-1 was achieved, and the enantiomerization barrier as well as important chiroptical properties of the individual enantiomers were determined in a combined experimental and theoretical effort.…”