The University of Southampton
University of Southampton Institutional Repository

Nine-ring angular fused biscarbazoloanthracene displaying a solid state based excimer emission suitable for OLED application

Nine-ring angular fused biscarbazoloanthracene displaying a solid state based excimer emission suitable for OLED application
Nine-ring angular fused biscarbazoloanthracene displaying a solid state based excimer emission suitable for OLED application
A new biscarbazoloanthracene consisting of nine fused aromatic rings, including two pyrrole units, has been obtained in a straightforward and convergent synthesis. Computational chemistry and conformational analysis revealed that the semiconductor’s molecule is not planar, the two carbazole moieties being helical twisted from the plane of the anthracene unit. Photophysical and electrochemical measurements showed that this angular fused heteroacene has a low lying HOMO energy level with a wide band gap despite its extended p-conjugated molecular framework. Based on its relatively low-lying HOMO level, the semiconductor promises a high environmental stability in comparison to other related linear fused acenes and heteroacenes. The biscarbazoloanthracene has been applied as the light emitting layer in a white light emitting diode (WOLED). It is proposed that the white OLED feature is due to dual light emission properties from the active semiconductor layer being based on both the molecular luminescence of the small molecule and a discrete excimer emission made possible by suitable aggregates in the solid state. Noteworthy, this is the first reported example of such a behavior observed in a small molecule heteroacene rather than an oligomer or a polymer.
2050-7526
5795-5805
Baryshnikov, Gleb V.
de2f286f-fd56-419f-a6fb-aa23abd22a83
Gawrys, Pawel
7e46d079-b298-4177-9b0c-bb0e1056fead
Ivaniuk, Khrystyna
a82a271b-1b1e-4907-9643-c8d3e083f164
Witulski, Bernhard
ffcefb33-a31d-489b-bc5a-f156961c57b9
Whitby, Richard J.
45632236-ab00-4ad0-a02d-6209043e818b
Al-Muhammad, Ayham
00e3ed42-320b-4c0c-9b1c-59d9466ed156
Minaev, Boris
38b79d26-1790-493e-9b7a-b51d4b30279f
Cherpak, Vladyslav
65809e96-9b74-4984-bb13-d9b84a53f89c
Stakhira, Pavlo
ad55f568-6860-40c8-9a10-1034e5481bd7
Volyniuk, Dmytro
2c451a48-73fa-4de4-908e-1512e4d9797e
Wiosna-Salyga, Gabriela
ea3b0dd1-cc67-4269-aeaa-14651b9969c5
Luszczynska, Beata
e1756eb5-7f8f-4c54-9c08-93e67d2c2626
Lazauskas, Algirdas
43d90ad4-b3b2-4d01-98f8-6b4580f1ab6e
Tamulevicius, Sigitas
94800a0a-5be4-42ff-b203-5d23b03fcd7c
Grazulevicius, Juozas V.
b52df429-883e-4f1b-a17b-dcd0c94a2457
Baryshnikov, Gleb V.
de2f286f-fd56-419f-a6fb-aa23abd22a83
Gawrys, Pawel
7e46d079-b298-4177-9b0c-bb0e1056fead
Ivaniuk, Khrystyna
a82a271b-1b1e-4907-9643-c8d3e083f164
Witulski, Bernhard
ffcefb33-a31d-489b-bc5a-f156961c57b9
Whitby, Richard J.
45632236-ab00-4ad0-a02d-6209043e818b
Al-Muhammad, Ayham
00e3ed42-320b-4c0c-9b1c-59d9466ed156
Minaev, Boris
38b79d26-1790-493e-9b7a-b51d4b30279f
Cherpak, Vladyslav
65809e96-9b74-4984-bb13-d9b84a53f89c
Stakhira, Pavlo
ad55f568-6860-40c8-9a10-1034e5481bd7
Volyniuk, Dmytro
2c451a48-73fa-4de4-908e-1512e4d9797e
Wiosna-Salyga, Gabriela
ea3b0dd1-cc67-4269-aeaa-14651b9969c5
Luszczynska, Beata
e1756eb5-7f8f-4c54-9c08-93e67d2c2626
Lazauskas, Algirdas
43d90ad4-b3b2-4d01-98f8-6b4580f1ab6e
Tamulevicius, Sigitas
94800a0a-5be4-42ff-b203-5d23b03fcd7c
Grazulevicius, Juozas V.
b52df429-883e-4f1b-a17b-dcd0c94a2457

Baryshnikov, Gleb V., Gawrys, Pawel, Ivaniuk, Khrystyna, Witulski, Bernhard, Whitby, Richard J., Al-Muhammad, Ayham, Minaev, Boris, Cherpak, Vladyslav, Stakhira, Pavlo, Volyniuk, Dmytro, Wiosna-Salyga, Gabriela, Luszczynska, Beata, Lazauskas, Algirdas, Tamulevicius, Sigitas and Grazulevicius, Juozas V. (2016) Nine-ring angular fused biscarbazoloanthracene displaying a solid state based excimer emission suitable for OLED application. Journal of Materials Chemistry C, 4 (24), 5795-5805. (doi:10.1039/C6TC01469K).

Record type: Article

Abstract

A new biscarbazoloanthracene consisting of nine fused aromatic rings, including two pyrrole units, has been obtained in a straightforward and convergent synthesis. Computational chemistry and conformational analysis revealed that the semiconductor’s molecule is not planar, the two carbazole moieties being helical twisted from the plane of the anthracene unit. Photophysical and electrochemical measurements showed that this angular fused heteroacene has a low lying HOMO energy level with a wide band gap despite its extended p-conjugated molecular framework. Based on its relatively low-lying HOMO level, the semiconductor promises a high environmental stability in comparison to other related linear fused acenes and heteroacenes. The biscarbazoloanthracene has been applied as the light emitting layer in a white light emitting diode (WOLED). It is proposed that the white OLED feature is due to dual light emission properties from the active semiconductor layer being based on both the molecular luminescence of the small molecule and a discrete excimer emission made possible by suitable aggregates in the solid state. Noteworthy, this is the first reported example of such a behavior observed in a small molecule heteroacene rather than an oligomer or a polymer.

Text
PG32_RSC_revised.pdf - Accepted Manuscript
Download (1MB)

More information

Submitted date: 11 April 2016
Accepted/In Press date: 23 May 2016
e-pub ahead of print date: 24 May 2016
Published date: 28 June 2016
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow

Identifiers

Local EPrints ID: 397464
URI: https://eprints.soton.ac.uk/id/eprint/397464
ISSN: 2050-7526
PURE UUID: 1a503a62-1af7-43ee-985e-3d1c4b7e31d7
ORCID for Richard J. Whitby: ORCID iD orcid.org/0000-0002-9891-5502

Catalogue record

Date deposited: 01 Jul 2016 11:06
Last modified: 15 Aug 2019 05:25

Export record

Altmetrics

Contributors

Author: Gleb V. Baryshnikov
Author: Pawel Gawrys
Author: Khrystyna Ivaniuk
Author: Bernhard Witulski
Author: Ayham Al-Muhammad
Author: Boris Minaev
Author: Vladyslav Cherpak
Author: Pavlo Stakhira
Author: Dmytro Volyniuk
Author: Gabriela Wiosna-Salyga
Author: Beata Luszczynska
Author: Algirdas Lazauskas
Author: Sigitas Tamulevicius
Author: Juozas V. Grazulevicius

University divisions

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of https://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×