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Carbonyl-Terminated Quinoidal Oligothiophenes as p-Type Organic Semiconductors

A series of quinoidal oligothiophenes terminated with carbonyl groups (nTDs, n = 2–4) are studied as p-type organic semiconductors for the active materials in organic field-effect transistors (OFETs) both by the theoretical and experimental approaches. The theoretical calculations clearly show their...

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Autores principales: Asoh, Takato, Kawabata, Kohsuke, Takimiya, Kazuo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7372439/
https://www.ncbi.nlm.nih.gov/pubmed/32640695
http://dx.doi.org/10.3390/ma13133020
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author Asoh, Takato
Kawabata, Kohsuke
Takimiya, Kazuo
author_facet Asoh, Takato
Kawabata, Kohsuke
Takimiya, Kazuo
author_sort Asoh, Takato
collection PubMed
description A series of quinoidal oligothiophenes terminated with carbonyl groups (nTDs, n = 2–4) are studied as p-type organic semiconductors for the active materials in organic field-effect transistors (OFETs) both by the theoretical and experimental approaches. The theoretical calculations clearly show their high-lying highest occupied molecular orbital (HOMO) energy levels (E(HOMO)s), small reorganization energies for hole transport (λ(hole)s), and large contribution of sulfur atoms to HOMOs, all of which are desirable for p-type organic semiconductors. Thus, we synthesized nTDs from the corresponding aromatic oligothiophene precursors and then evaluated their physicochemical properties and structural properties. These experimental evaluations of nTDs nicely proved the theoretical predictions, and the largest 4TDs in the series (4,4′′′-dihexyl- and 3′,4,4″,4′′′-tetrahexyl-5H,5′′′H-[2,2′:5′,2″:5″,2′′′-quaterthiophene]-5,5′′′-dione) can afford solution-processed OFETs showing unipolar p-type behaviors and hole mobility as high as 0.026 cm(2) V(−1) s(−1).
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spelling pubmed-73724392020-08-05 Carbonyl-Terminated Quinoidal Oligothiophenes as p-Type Organic Semiconductors Asoh, Takato Kawabata, Kohsuke Takimiya, Kazuo Materials (Basel) Article A series of quinoidal oligothiophenes terminated with carbonyl groups (nTDs, n = 2–4) are studied as p-type organic semiconductors for the active materials in organic field-effect transistors (OFETs) both by the theoretical and experimental approaches. The theoretical calculations clearly show their high-lying highest occupied molecular orbital (HOMO) energy levels (E(HOMO)s), small reorganization energies for hole transport (λ(hole)s), and large contribution of sulfur atoms to HOMOs, all of which are desirable for p-type organic semiconductors. Thus, we synthesized nTDs from the corresponding aromatic oligothiophene precursors and then evaluated their physicochemical properties and structural properties. These experimental evaluations of nTDs nicely proved the theoretical predictions, and the largest 4TDs in the series (4,4′′′-dihexyl- and 3′,4,4″,4′′′-tetrahexyl-5H,5′′′H-[2,2′:5′,2″:5″,2′′′-quaterthiophene]-5,5′′′-dione) can afford solution-processed OFETs showing unipolar p-type behaviors and hole mobility as high as 0.026 cm(2) V(−1) s(−1). MDPI 2020-07-06 /pmc/articles/PMC7372439/ /pubmed/32640695 http://dx.doi.org/10.3390/ma13133020 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Asoh, Takato
Kawabata, Kohsuke
Takimiya, Kazuo
Carbonyl-Terminated Quinoidal Oligothiophenes as p-Type Organic Semiconductors
title Carbonyl-Terminated Quinoidal Oligothiophenes as p-Type Organic Semiconductors
title_full Carbonyl-Terminated Quinoidal Oligothiophenes as p-Type Organic Semiconductors
title_fullStr Carbonyl-Terminated Quinoidal Oligothiophenes as p-Type Organic Semiconductors
title_full_unstemmed Carbonyl-Terminated Quinoidal Oligothiophenes as p-Type Organic Semiconductors
title_short Carbonyl-Terminated Quinoidal Oligothiophenes as p-Type Organic Semiconductors
title_sort carbonyl-terminated quinoidal oligothiophenes as p-type organic semiconductors
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7372439/
https://www.ncbi.nlm.nih.gov/pubmed/32640695
http://dx.doi.org/10.3390/ma13133020
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AT takimiyakazuo carbonylterminatedquinoidaloligothiophenesasptypeorganicsemiconductors