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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2022
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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). |
format | Online Article Text |
id | pubmed-9359197 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
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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