Synthesis and optoelectronic properties of benzoquinone-based donor–acceptor compounds

Abstract

Herein, we report a mild and efficient palladium-catalyzed C–H functionalization method to synthesize a series of benzoquinone (BQ)-based charge-transfer (CT) derivatives in good yields. The optoelectronic properties of these compounds were explored both theoretically and experimentally and correlations to their structures were identified as a function of the nature and position of the donor group (meta and para) attached to the benzoquinone acceptor. Compound 3, where benzoquinone is para-conjugated to the diphenylamine donor group, exhibited thermally activated delayed fluorescence (TADF) with a biexponential lifetime characterized by a prompt ns component and a delayed component of 353 μs.

Thermally activated delayed fluorescence emitters showing wide-range near-infrared piezochromism and their use in deep-red OLEDs

“…Both compounds show two highly reversible reduction waves, typical behavior of the benzoquinone moiety. 20 The first reduction potentials are −0.78, −0.79 and −0.76 V for MeTPA-BQ, tBuTPA-BQ and TPPA-BQ respectively. The respective estimated LUMO energy levels are −3.56, −3.55 and −3.58 eV, following the trends predicted by DFT calculations that the LUMO energy level of TPPA-BQ is stabilized in comparison to MeTPA-BQ and tBuTPA-BQ (Table S2 † ).…”

Triphenylamine‐Supported Benzoquinone Polymer as High Performance Cathode for Lithium‐Ion Batteries

“…Figure S1 and S2 (Supporting Information) about 1 H NMR and 13 C NMR spectrums indicate seven different types of hydrogen and twelve different types of carbon in various situations well correspond to the molecular structure characteristics for TPA-BQ, which were similar with the reported results. [33] In order to further ascertain the structure of TPA-BQ and PTPA-BQ, FTIR spectroscopy was utilized to determine the function groups of TPA-BQ and PTPA-BQ (Figure 1b). Obviously, polymer PTPA-BQ and monomer TPA-BQ show almost same IR spectrums.…”