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Medium Diradical Character, Small Hole and Electron Reorganization Energies and Ambipolar Transistors in Difluorenoheteroles

Four difluorenoheteroles having a central quinoidal core with the heteroring varying as furan, thiophene, its dioxide derivative and pyrrole have shown to be medium character diradicals. Solid‐state structures, optical, photophysical, magnetic, and electrochemical properties have been discussed in t...

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Autores principales: Mori, Sakura, Moles Quintero, Sergio, Tabaka, Naoki, Kishi, Ryohei, González Núñez, Raúl, Harbuzaru, Alexandra, Ponce Ortiz, Rocío, Marín‐Beloqui, Jose, Suzuki, Shuichi, Kitamura, Chitoshi, Gómez‐García, Carlos J., Dai, Yasi, Negri, Fabrizia, Nakano, Masayoshi, Kato, Shin‐ichiro, Casado, Juan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9542770/
https://www.ncbi.nlm.nih.gov/pubmed/35696258
http://dx.doi.org/10.1002/anie.202206680
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author Mori, Sakura
Moles Quintero, Sergio
Tabaka, Naoki
Kishi, Ryohei
González Núñez, Raúl
Harbuzaru, Alexandra
Ponce Ortiz, Rocío
Marín‐Beloqui, Jose
Suzuki, Shuichi
Kitamura, Chitoshi
Gómez‐García, Carlos J.
Dai, Yasi
Negri, Fabrizia
Nakano, Masayoshi
Kato, Shin‐ichiro
Casado, Juan
author_facet Mori, Sakura
Moles Quintero, Sergio
Tabaka, Naoki
Kishi, Ryohei
González Núñez, Raúl
Harbuzaru, Alexandra
Ponce Ortiz, Rocío
Marín‐Beloqui, Jose
Suzuki, Shuichi
Kitamura, Chitoshi
Gómez‐García, Carlos J.
Dai, Yasi
Negri, Fabrizia
Nakano, Masayoshi
Kato, Shin‐ichiro
Casado, Juan
author_sort Mori, Sakura
collection PubMed
description Four difluorenoheteroles having a central quinoidal core with the heteroring varying as furan, thiophene, its dioxide derivative and pyrrole have shown to be medium character diradicals. Solid‐state structures, optical, photophysical, magnetic, and electrochemical properties have been discussed in terms of diradical character, variation of aromatic character and captodative effects (electron affinity). Organic field‐effect transistors (OFETs) have been prepared, showing balanced hole and electron mobilities of the order of 10(−3) cm(2) V(−1) s(−1) or ambipolar charge transport which is first inferred from their redox amphoterism. Quantum chemical calculations show that the electrical behavior is originated from the medium diradical character which produces similar reorganization energies for hole and electron transports. The vision of a diradical as simultaneously bearing pseudo‐hole and pseudo‐electron defects might justify the reduced values of reorganization energies for both regimes. Structure‐function relationships between diradical and ambipolar electrical behavior are revealed.
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spelling pubmed-95427702022-10-14 Medium Diradical Character, Small Hole and Electron Reorganization Energies and Ambipolar Transistors in Difluorenoheteroles Mori, Sakura Moles Quintero, Sergio Tabaka, Naoki Kishi, Ryohei González Núñez, Raúl Harbuzaru, Alexandra Ponce Ortiz, Rocío Marín‐Beloqui, Jose Suzuki, Shuichi Kitamura, Chitoshi Gómez‐García, Carlos J. Dai, Yasi Negri, Fabrizia Nakano, Masayoshi Kato, Shin‐ichiro Casado, Juan Angew Chem Int Ed Engl Research Articles Four difluorenoheteroles having a central quinoidal core with the heteroring varying as furan, thiophene, its dioxide derivative and pyrrole have shown to be medium character diradicals. Solid‐state structures, optical, photophysical, magnetic, and electrochemical properties have been discussed in terms of diradical character, variation of aromatic character and captodative effects (electron affinity). Organic field‐effect transistors (OFETs) have been prepared, showing balanced hole and electron mobilities of the order of 10(−3) cm(2) V(−1) s(−1) or ambipolar charge transport which is first inferred from their redox amphoterism. Quantum chemical calculations show that the electrical behavior is originated from the medium diradical character which produces similar reorganization energies for hole and electron transports. The vision of a diradical as simultaneously bearing pseudo‐hole and pseudo‐electron defects might justify the reduced values of reorganization energies for both regimes. Structure‐function relationships between diradical and ambipolar electrical behavior are revealed. John Wiley and Sons Inc. 2022-07-04 2022-08-15 /pmc/articles/PMC9542770/ /pubmed/35696258 http://dx.doi.org/10.1002/anie.202206680 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ (https://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Research Articles
Mori, Sakura
Moles Quintero, Sergio
Tabaka, Naoki
Kishi, Ryohei
González Núñez, Raúl
Harbuzaru, Alexandra
Ponce Ortiz, Rocío
Marín‐Beloqui, Jose
Suzuki, Shuichi
Kitamura, Chitoshi
Gómez‐García, Carlos J.
Dai, Yasi
Negri, Fabrizia
Nakano, Masayoshi
Kato, Shin‐ichiro
Casado, Juan
Medium Diradical Character, Small Hole and Electron Reorganization Energies and Ambipolar Transistors in Difluorenoheteroles
title Medium Diradical Character, Small Hole and Electron Reorganization Energies and Ambipolar Transistors in Difluorenoheteroles
title_full Medium Diradical Character, Small Hole and Electron Reorganization Energies and Ambipolar Transistors in Difluorenoheteroles
title_fullStr Medium Diradical Character, Small Hole and Electron Reorganization Energies and Ambipolar Transistors in Difluorenoheteroles
title_full_unstemmed Medium Diradical Character, Small Hole and Electron Reorganization Energies and Ambipolar Transistors in Difluorenoheteroles
title_short Medium Diradical Character, Small Hole and Electron Reorganization Energies and Ambipolar Transistors in Difluorenoheteroles
title_sort medium diradical character, small hole and electron reorganization energies and ambipolar transistors in difluorenoheteroles
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9542770/
https://www.ncbi.nlm.nih.gov/pubmed/35696258
http://dx.doi.org/10.1002/anie.202206680
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