Short axially asymmetrically 1,3-disubstituted pyrene-based color-tunable emitters: Synthesis, characterization and optical properties

Abstract

In contrast to conventional pyrene-based emitters which feature D-π-A type structures, a new class of emitters possessing a short axis are gaining interest owing to both their academic importance and promising applications in organic optoelectronic materials. Herein, donor and acceptor substituents were introduced at 1-, 3-positions by employing a two step bromination reaction. Two 1-donor-3-acceptor pyrenes were systematically investigated by 1 H/ 13 C NMR spectroscopy, optical spectroscopy, and theoretical calculations. The preliminary research of the substituent positions and substitutions pattern on the properties of the materials as well as on the frontier orbitals is reported. The experimental results indicated the strong impact on the photophysical properties endowed with the possibility of precise color-control of pyrene derivatives through substituent variation. A strategy to access a new class of D-π-A pyrene-based emitters has been established. The strategy is not only useful in the design of novel chromophores but it could also enable the preparation of high-efficiency opto-electronic materials. • A new class of D-π-A pyrene-based emitters at 1,3-positions on pyrene ring was successfully designed and synthesized. • Short axially asymmetrically 1-donor-3-acceptor pyrenes, two compounds exhibit efficient color-tunable properties. • Two compounds exhibit high thermal stability and good solubility.