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

A novel π-conjugated molecule, EtH-T-DI-DTT is reported, which is fused, rigid, and planar, featuring the electron-rich dithieno[3,2-b:2’,3’-d]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...

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Autores principales: Fell, Valentin H K, Cameron, Joseph, Kanibolotsky, Alexander L, Hussien, Eman J, Skabara, Peter J
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9359197/
https://www.ncbi.nlm.nih.gov/pubmed/35965856
http://dx.doi.org/10.3762/bjoc.18.94
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author Fell, Valentin H K
Cameron, Joseph
Kanibolotsky, Alexander L
Hussien, Eman J
Skabara, Peter J
author_facet Fell, Valentin H K
Cameron, Joseph
Kanibolotsky, Alexander L
Hussien, Eman J
Skabara, Peter J
author_sort Fell, Valentin H K
collection PubMed
description A novel π-conjugated molecule, EtH-T-DI-DTT is reported, which is fused, rigid, and planar, featuring the electron-rich dithieno[3,2-b:2’,3’-d]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(2)Cl(2) 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(−4) cm(2) V(−1) s(−1).
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spelling pubmed-93591972022-08-12 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, Valentin H K Cameron, Joseph Kanibolotsky, Alexander L Hussien, Eman J Skabara, Peter J Beilstein J Org Chem Full Research Paper A novel π-conjugated molecule, EtH-T-DI-DTT is reported, which is fused, rigid, and planar, featuring the electron-rich dithieno[3,2-b:2’,3’-d]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(2)Cl(2) 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(−4) cm(2) V(−1) s(−1). Beilstein-Institut 2022-08-01 /pmc/articles/PMC9359197/ /pubmed/35965856 http://dx.doi.org/10.3762/bjoc.18.94 Text en Copyright © 2022, Fell et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Full Research Paper
Fell, Valentin H K
Cameron, Joseph
Kanibolotsky, Alexander L
Hussien, Eman J
Skabara, Peter J
Introducing a new 7-ring fused diindenone-dithieno[3,2-b:2',3'-d]thiophene unit as a promising component for organic semiconductor materials
title Introducing a new 7-ring fused diindenone-dithieno[3,2-b:2',3'-d]thiophene unit as a promising component for organic semiconductor materials
title_full Introducing a new 7-ring fused diindenone-dithieno[3,2-b:2',3'-d]thiophene unit as a promising component for organic semiconductor materials
title_fullStr Introducing a new 7-ring fused diindenone-dithieno[3,2-b:2',3'-d]thiophene unit as a promising component for organic semiconductor materials
title_full_unstemmed Introducing a new 7-ring fused diindenone-dithieno[3,2-b:2',3'-d]thiophene unit as a promising component for organic semiconductor materials
title_short Introducing a new 7-ring fused diindenone-dithieno[3,2-b:2',3'-d]thiophene unit as a promising component for organic semiconductor materials
title_sort introducing a new 7-ring fused diindenone-dithieno[3,2-b:2',3'-d]thiophene unit as a promising component for organic semiconductor materials
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9359197/
https://www.ncbi.nlm.nih.gov/pubmed/35965856
http://dx.doi.org/10.3762/bjoc.18.94
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