Scale-up chemical synthesis of thermally-activated delayed fluorescence emitters based on the dibenzothiophene-S,S-dioxide core

Vybornyi, Oleh and Findlay, Neil J. and Skabara, Peter J. (2017) Scale-up chemical synthesis of thermally-activated delayed fluorescence emitters based on the dibenzothiophene-S,S-dioxide core. Journal of Visualized Experiments, 2017 (128). e56501. ISSN 1940-087X (https://doi.org/10.3791/56501)

[thumbnail of Vybornyi-etal-JVE-2017-Scale-up-chemical-synthesis-of-thermally-activated-delayed-fluorescence-emitters]
Preview
 Text. Filename: Vybornyi_etal_JVE_2017_Scale_up_chemical_synthesis_of_thermally_activated_delayed_fluorescence_emitters.pdf
Final Published Version
License: Creative Commons Attribution 3.0 logo
Download (254kB)| Preview

Abstract

We report a procedure to linearly scale-up the synthesis of 2,8-bis(3,6-di-tert-butyl-9H-carbazol-9-yl)dibenzothiophene-S,S-dioxide (compound 4) and 2,8-bis(10H-phenothiazin-10-yl)dibenzothiophene-S,S-dioxide (compound 5) using Buchwald-Hartwig cross-coupling reaction conditions. In addition, we demonstrate a scaled-up synthesis of all non-commercially available starting materials that are required for the amination cross-coupling reaction. In the present article, we provide the detailed synthetic procedures for all of the described compounds, alongside their spectral characterization. This work shows the possibility to produce organic molecules for optoelectronic applications on a large scale, which facilitates their implementation into real world devices.

ORCID iDs

Vybornyi, Oleh, Findlay, Neil J. ORCID logoORCID: https://orcid.org/0000-0002-1417-3311 and Skabara, Peter J.;
CORE (COnnecting REpositories)