The University of Southampton
University of Southampton Institutional Repository

Modular synthesis of unsymmetrical [1]benzothieno[3,2-b] [1]benzothiophene molecular semiconductors for organic transistors

Modular synthesis of unsymmetrical [1]benzothieno[3,2-b] [1]benzothiophene molecular semiconductors for organic transistors
Modular synthesis of unsymmetrical [1]benzothieno[3,2-b] [1]benzothiophene molecular semiconductors for organic transistors

A modular approach to underexplored, unsymmetrical [1]benzothieno[3,2-b][1]benzothiophene (BTBT) scaffolds delivers a library of BTBT materials from readily available coupling partners by combining a transition-metal free Pummerer CH-CH-type cross-coupling and a Newman-Kwart reaction. This effective approach to unsymmetrical BTBT materials has allowed their properties to be studied. In particular, tuning the functional groups on the BTBT scaffold allows the solid-state assembly and molecular orbital energy levels to be modulated. Investigation of the charge transport properties of BTBT-containing small-molecule:polymer blends revealed the importance of molecular ordering during phase segregation and matching the highest occupied molecular orbital energy level with that of the semiconducting polymer binder, polyindacenodithiophene-benzothiadiazole (PIDTBT). The hole mobilities extracted from transistors fabricated using blends of PIDTBT with phenyl or methoxy functionalized unsymmetrical BTBTs were double those measured for devices fabricated using pristine PIDTBT. This study underscores the value of the synthetic methodology in providing a platform from which to study structure-property relationships in an underrepresented family of unsymmetrical BTBT molecular semiconductors.

2041-6520
421-429
Tayu, Masanori
bc6b05c3-0ce1-4035-999e-049c9fa0c0ea
Rahmanudin, Aiman
eb0e80d1-709a-4f11-8ede-4e4fcdc51d32
Perry, Gregory J.P.
766e7fc8-abf3-4d1e-9949-c1b3439a2185
Khan, Raja U.
1132858f-0925-4487-b03f-21e16c63098c
Tate, Daniel J.
e0db072e-a7a3-48ee-b6cf-3271306d75df
Marcial-Hernandez, Raymundo
79455644-e8fe-49b8-ac67-2dbd5de6b17b
Shen, Yuan
a3058aeb-2be6-4d21-bd71-d4e59d97712c
Dierking, Ingo
d53ec8d9-2da8-4b11-9029-b9365d6a08be
Janpatompong, Yurachat
eb653659-edfa-4803-90a1-b4187016d456
Aphichatpanichakul, Suphaluk
1a2849ba-90bd-435a-ae45-8030ed1c8f13
Zamhuri, Adibah
ce50ee06-1692-4ce9-86a3-2a5b130a6161
Victoria-Yrezabal, Inigo
c473a6e7-2325-4003-922a-b524445ce1d9
Turner, Michael L.
08ce31e0-a027-4af2-ac20-d704c909b49e
Procter, David J.
7642b405-d26f-4064-b0d2-8a1d562348b4
Tayu, Masanori
bc6b05c3-0ce1-4035-999e-049c9fa0c0ea
Rahmanudin, Aiman
eb0e80d1-709a-4f11-8ede-4e4fcdc51d32
Perry, Gregory J.P.
766e7fc8-abf3-4d1e-9949-c1b3439a2185
Khan, Raja U.
1132858f-0925-4487-b03f-21e16c63098c
Tate, Daniel J.
e0db072e-a7a3-48ee-b6cf-3271306d75df
Marcial-Hernandez, Raymundo
79455644-e8fe-49b8-ac67-2dbd5de6b17b
Shen, Yuan
a3058aeb-2be6-4d21-bd71-d4e59d97712c
Dierking, Ingo
d53ec8d9-2da8-4b11-9029-b9365d6a08be
Janpatompong, Yurachat
eb653659-edfa-4803-90a1-b4187016d456
Aphichatpanichakul, Suphaluk
1a2849ba-90bd-435a-ae45-8030ed1c8f13
Zamhuri, Adibah
ce50ee06-1692-4ce9-86a3-2a5b130a6161
Victoria-Yrezabal, Inigo
c473a6e7-2325-4003-922a-b524445ce1d9
Turner, Michael L.
08ce31e0-a027-4af2-ac20-d704c909b49e
Procter, David J.
7642b405-d26f-4064-b0d2-8a1d562348b4

Tayu, Masanori, Rahmanudin, Aiman, Perry, Gregory J.P., Khan, Raja U., Tate, Daniel J., Marcial-Hernandez, Raymundo, Shen, Yuan, Dierking, Ingo, Janpatompong, Yurachat, Aphichatpanichakul, Suphaluk, Zamhuri, Adibah, Victoria-Yrezabal, Inigo, Turner, Michael L. and Procter, David J. (2022) Modular synthesis of unsymmetrical [1]benzothieno[3,2-b] [1]benzothiophene molecular semiconductors for organic transistors. Chemical Science, 13 (2), 421-429. (doi:10.1039/d1sc05070b).

Record type: Article

Abstract

A modular approach to underexplored, unsymmetrical [1]benzothieno[3,2-b][1]benzothiophene (BTBT) scaffolds delivers a library of BTBT materials from readily available coupling partners by combining a transition-metal free Pummerer CH-CH-type cross-coupling and a Newman-Kwart reaction. This effective approach to unsymmetrical BTBT materials has allowed their properties to be studied. In particular, tuning the functional groups on the BTBT scaffold allows the solid-state assembly and molecular orbital energy levels to be modulated. Investigation of the charge transport properties of BTBT-containing small-molecule:polymer blends revealed the importance of molecular ordering during phase segregation and matching the highest occupied molecular orbital energy level with that of the semiconducting polymer binder, polyindacenodithiophene-benzothiadiazole (PIDTBT). The hole mobilities extracted from transistors fabricated using blends of PIDTBT with phenyl or methoxy functionalized unsymmetrical BTBTs were double those measured for devices fabricated using pristine PIDTBT. This study underscores the value of the synthetic methodology in providing a platform from which to study structure-property relationships in an underrepresented family of unsymmetrical BTBT molecular semiconductors.

Text
d1sc05070b - Version of Record
Available under License Creative Commons Attribution.
Download (1MB)

More information

Accepted/In Press date: 27 November 2021
e-pub ahead of print date: 29 November 2021
Published date: 14 January 2022
Additional Information: Funding Information: The authors gratefully acknowledge nancial support from The Uehara Memorial Foundation (Fellowship to M. T.) and the Engineering and Physical Sciences Research Council (EPSRC) through the Centre for Innovative Manufacturing in Large Area Electronics (CIMLAE, program grant EP/K03099X/1) and the iUK grant PlasticARMPIT (103390). R. M.-H. acknowledges the support of a Consejo Nacional de Ciencia y Tecnología (CON-ACYT) Mexico Scholarship (478743) and R. U. K. an EPSRC Doctoral Training Program Health Care Technology Studentship. We thank the University of Manchester (Lectureship to G. J. P. P.) for their generous support. Publisher Copyright: © The Royal Society of Chemistry.

Identifiers

Local EPrints ID: 476937
URI: http://eprints.soton.ac.uk/id/eprint/476937
ISSN: 2041-6520
PURE UUID: 2e4621bf-5f0b-4415-87a4-83d703e23761
ORCID for Gregory J.P. Perry: ORCID iD orcid.org/0000-0001-8173-3369

Catalogue record

Date deposited: 19 May 2023 16:47
Last modified: 06 Jun 2024 02:17

Export record

Altmetrics

Contributors

Author: Masanori Tayu
Author: Aiman Rahmanudin
Author: Gregory J.P. Perry ORCID iD
Author: Raja U. Khan
Author: Daniel J. Tate
Author: Raymundo Marcial-Hernandez
Author: Yuan Shen
Author: Ingo Dierking
Author: Yurachat Janpatompong
Author: Suphaluk Aphichatpanichakul
Author: Adibah Zamhuri
Author: Inigo Victoria-Yrezabal
Author: Michael L. Turner
Author: David J. Procter

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 http://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.

×