The influence of alkyl group regiochemistry and backbone fluorination on the packing and transistor performance of N-cyanoimine functionalised indacenodithiophenes
File(s)
Published version
Author(s)
Type
Journal Article
Abstract
The synthesis of two novel n-type molecular organic semiconductors based on a fluorinated indacenodithiophene core in combination with an electron withdrawing N-cyanoimine group is reported, and the influence of the regiochemistry of the solubilizing sidechain is investigated. The N-cyanoimine is confirmed to be a strongly electron accepting group, which in combination with the core fluorination resulted in high electron affinities for both materials. Single crystal analysis demonstrated that whilst both materials arrange in ordered slipped stacks with close π–π stacking distances (∼3.40 Å), significant differences in electron transfer integrals for the two regioisomers were observed, relating to differences in relative molecular displacement along the π-stacking direction. Organic thin-film transistors fabricated via blade-coating displayed electron mobility up to 0.13 cm2 V−1 s−1 for the isomer with the larger transfer integral.
Date Issued
2021-03-07
Date Acceptance
2021-02-02
Citation
Materials Advances, 2021, 2 (5), pp.1706-1714
Publisher
Wiley
Start Page
1706
End Page
1714
Journal / Book Title
Materials Advances
Volume
2
Issue
5
Copyright Statement
© 2021 The Author(s). Published by the Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
License URL
Sponsor
FWF Austrian Science Fund (FWF)
Identifier
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000629901500019&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=1ba7043ffcc86c417c072aa74d649202
Grant Number
J 4463
Subjects
Science & Technology
Technology
Materials Science, Multidisciplinary
Materials Science
CHANNEL ORGANIC TRANSISTORS
FIELD-EFFECT TRANSISTORS
SEMICONDUCTING POLYMERS
DESIGN STRATEGIES
CHARGE-TRANSPORT
THIOPHENE
DCNQI
Publication Status
Published
Date Publish Online
2021-02-03