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

Vybornyi, O., Findlay, N. and Skabara, P. J. (2017) Scale-up chemical synthesis of thermally-activated delayed fluorescence emitters based on the dibenzothiophene-S,S-dioxide core. Journal of Visualized Experiments(128), e56501. (doi: 10.3791/56501) (PMID:29155783) (PMCID:PMC5755231)

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 crosscoupling 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.

• Item Type: Articles
• Additional Information: This research has received funding from the European Union's Horizon 2020 research and innovation program under the Marie SkłodowskaCurie grant agreement H2020-MSCA-ITN-2015/674990 project "EXCILIGHT". PJS thanks the Royal Society for a Wolfson Research Merit Award.
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Vybornyi, Mr Oleh and Skabara, Professor Peter and Findlay, Dr Neil
• Authors: Vybornyi, O., Findlay, N., and Skabara, P. J.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Journal of Visualized Experiments
• Publisher: Journal of Visualized Experiments
• ISSN: 1940-087X
• Copyright Holders: Copyright © 2017 The Authors
• First Published: First published in Journal of Visualized Experiments 128: e56501
• Publisher Policy: Reproduced under a Creative Commons License