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

Oleh Vybornyi, Neil J. Findlay, Peter J. Skabara

Research output: Contribution to journalArticle

2 Citations (Scopus)

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.

LanguageEnglish
Article numbere56501
Number of pages5
JournalJournal of Visualized Experiments
Volume2017
Issue number128
DOIs
Publication statusPublished - 24 Oct 2017

Fingerprint

Cross Reactions
Fluorescence
Amination
Optoelectronic devices
Equipment and Supplies
Molecules
dibenzothiophene

Keywords

  • Buchwald-Hartwig amination
  • chemistry
  • fluorescence
  • Pd cross-coupling
  • OLED
  • synthesis
  • TADF

Cite this

@article{1602da19760d49a5969fd67299ad3a98,
title = "Scale-up chemical synthesis of thermally-activated delayed fluorescence emitters based on the dibenzothiophene-S,S-dioxide core",
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.",
keywords = "Buchwald-Hartwig amination, chemistry, fluorescence, Pd cross-coupling, OLED, synthesis, TADF",
author = "Oleh Vybornyi and Findlay, {Neil J.} and Skabara, {Peter J.}",
year = "2017",
month = "10",
day = "24",
doi = "10.3791/56501",
language = "English",
volume = "2017",
journal = "The Journal of Visualized Experiments",
issn = "1940-087X",
number = "128",

}

Scale-up chemical synthesis of thermally-activated delayed fluorescence emitters based on the dibenzothiophene-S,S-dioxide core. / Vybornyi, Oleh; Findlay, Neil J.; Skabara, Peter J.

In: Journal of Visualized Experiments, Vol. 2017, No. 128, e56501, 24.10.2017.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Scale-up chemical synthesis of thermally-activated delayed fluorescence emitters based on the dibenzothiophene-S,S-dioxide core

AU - Vybornyi, Oleh

AU - Findlay, Neil J.

AU - Skabara, Peter J.

PY - 2017/10/24

Y1 - 2017/10/24

N2 - 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.

AB - 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.

KW - Buchwald-Hartwig amination

KW - chemistry

KW - fluorescence

KW - Pd cross-coupling

KW - OLED

KW - synthesis

KW - TADF

UR - http://www.scopus.com/inward/record.url?scp=85034080860&partnerID=8YFLogxK

U2 - 10.3791/56501

DO - 10.3791/56501

M3 - Article

VL - 2017

JO - The Journal of Visualized Experiments

T2 - The Journal of Visualized Experiments

JF - The Journal of Visualized Experiments

SN - 1940-087X

IS - 128

M1 - e56501

ER -