Introducing a new 7-ring fused diindenone-dithieno[3,2-b:2',3'-d]thiophene unit as a promising component for organic semiconductor materials

Fell, V. H.K., Cameron, J. , Kanibolotsky, A. L., Hussien, E. J. and Skabara, P. J. (2022) Introducing a new 7-ring fused diindenone-dithieno[3,2-b:2',3'-d]thiophene unit as a promising component for organic semiconductor materials. Beilstein Journal of Organic Chemistry, 18, pp. 944-955. (doi: 10.3762/bjoc.18.94) (PMID:35965856) (PMCID:PMC9359197)

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Abstract

A novel π-conjugated molecule, is reported, which is fused, rigid, and planar, featuring the electron-rich dithieno[3,2- :2',3'- ]thiophene (DTT) unit in the core of the structure. Adjacent to the electron-donating DTT core, there are indenone units with electron-withdrawing keto groups. To enable solubility in common organic solvents, the fused system is flanked by ethylhexylthiophene groups. The material is a dark, amorphous solid with an onset of absorption at 638 nm in CH Cl solution, which corresponds to an optical gap of 1.94 eV. In films, the absorption onset wavelength is at 701 nm, which corresponds to 1.77 eV. An ionisation energy of 5.5 eV and an electron affinity of 3.3 eV were estimated by cyclic voltammetry measurements. We have applied this new molecule in organic field effect transistors. The material exhibited a p-type mobility up to 1.33 × 10 cm V s . [Abstract copyright: Copyright © 2022, Fell et al.]

Item Type:Articles
Keywords:Thienoacene, organic semiconductor, organic field-effect transistor (OFET), dithienothiophene (DTT), fused ring system.
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Fell, Valentin and Kanibolotskyy, Dr Oleksandr and Cameron, Dr Joseph and Hussien, Eman and Skabara, Professor Peter
Authors: Fell, V. H.K., Cameron, J., Kanibolotsky, A. L., Hussien, E. J., and Skabara, P. J.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Beilstein Journal of Organic Chemistry
Publisher:Beilstein-Institut
ISSN:1860-5397
ISSN (Online):1860-5397
Published Online:01 August 2022
Copyright Holders:Copyright © 2022 Fell et al.
First Published:First published in Beilstein Journal of Organic Chemistry 18: 944-955
Publisher Policy:Reproduced under a Creative Commons License

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
303776Light-controlled manufacturing of semiconductor structures: a platform for next generation processing of photonic devicesPeter SkabaraEngineering and Physical Sciences Research Council (EPSRC)EP/P02744X/2Chemistry
301327`Hetero-print: A holistic approach to transfer-printing for heterogeneous integration in manufacturingPeter SkabaraEngineering and Physical Sciences Research Council (EPSRC)EP/R03480X/1ENG - Electronics & Nanoscale Engineering