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Fluorination Induced Donor to Acceptor Transformation in A1–D–A2–D–A1-Type Photovoltaic Small Molecules

With the development of diversity of non-fullerene acceptors, it is found that there is no clear boundary between electron donors and electron acceptors. Modulation of the electron donating and withdrawing properties of organic semiconductors is necessary for organic photovoltaics research. In this...

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Autores principales: Zhou, Ruimin, Xia, Benzheng, Li, Huan, Wang, Zhen, Yang, Yang, Zhang, Jianqi, Laursen, Bo W., Lu, Kun, Wei, Zhixiang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6127638/
https://www.ncbi.nlm.nih.gov/pubmed/30234102
http://dx.doi.org/10.3389/fchem.2018.00384
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author Zhou, Ruimin
Xia, Benzheng
Li, Huan
Wang, Zhen
Yang, Yang
Zhang, Jianqi
Laursen, Bo W.
Lu, Kun
Wei, Zhixiang
author_facet Zhou, Ruimin
Xia, Benzheng
Li, Huan
Wang, Zhen
Yang, Yang
Zhang, Jianqi
Laursen, Bo W.
Lu, Kun
Wei, Zhixiang
author_sort Zhou, Ruimin
collection PubMed
description With the development of diversity of non-fullerene acceptors, it is found that there is no clear boundary between electron donors and electron acceptors. Modulation of the electron donating and withdrawing properties of organic semiconductors is necessary for organic photovoltaics research. In this work, we designed and synthesized three A1–D–A2–D–A1-type (A represents acceptor unit and D represents donor unit) small molecules, named as M-0F, M-1F, and M-2F, respectively containing zero, one, and two fluorine atoms in the terminal acceptor segments (A1), respectively. Fluorination substitution was found to be able to downshift the HOMO and LUMO energy level, red-shift the absorption, and enhance the electron mobility. The M-0F exhibited the highest efficiency of 5.99% as a donor in fullerene-containing system and the lowest efficiency of 0.58% as an acceptor in fullerene-free system. While the M-2F performed the lowest efficiency of 0.97% as the donor and the highest efficiency of 2.65% as the acceptor. The electron-donating and electron-withdrawing property of M-1F are in-between that of M-0F and M-2F. Among the three molecules, the electron mobility is increased while the hole mobility is decreased with increasing fluorination. This work provides a typical example of tuning of the electron donating and withdrawing property without changes to the backbone of the conjugated molecules, which is important for further designing high performance solution processable small molecules.
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spelling pubmed-61276382018-09-19 Fluorination Induced Donor to Acceptor Transformation in A1–D–A2–D–A1-Type Photovoltaic Small Molecules Zhou, Ruimin Xia, Benzheng Li, Huan Wang, Zhen Yang, Yang Zhang, Jianqi Laursen, Bo W. Lu, Kun Wei, Zhixiang Front Chem Chemistry With the development of diversity of non-fullerene acceptors, it is found that there is no clear boundary between electron donors and electron acceptors. Modulation of the electron donating and withdrawing properties of organic semiconductors is necessary for organic photovoltaics research. In this work, we designed and synthesized three A1–D–A2–D–A1-type (A represents acceptor unit and D represents donor unit) small molecules, named as M-0F, M-1F, and M-2F, respectively containing zero, one, and two fluorine atoms in the terminal acceptor segments (A1), respectively. Fluorination substitution was found to be able to downshift the HOMO and LUMO energy level, red-shift the absorption, and enhance the electron mobility. The M-0F exhibited the highest efficiency of 5.99% as a donor in fullerene-containing system and the lowest efficiency of 0.58% as an acceptor in fullerene-free system. While the M-2F performed the lowest efficiency of 0.97% as the donor and the highest efficiency of 2.65% as the acceptor. The electron-donating and electron-withdrawing property of M-1F are in-between that of M-0F and M-2F. Among the three molecules, the electron mobility is increased while the hole mobility is decreased with increasing fluorination. This work provides a typical example of tuning of the electron donating and withdrawing property without changes to the backbone of the conjugated molecules, which is important for further designing high performance solution processable small molecules. Frontiers Media S.A. 2018-08-30 /pmc/articles/PMC6127638/ /pubmed/30234102 http://dx.doi.org/10.3389/fchem.2018.00384 Text en Copyright © 2018 Zhou, Xia, Li, Wang, Yang, Zhang, Laursen, Lu and Wei. http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Zhou, Ruimin
Xia, Benzheng
Li, Huan
Wang, Zhen
Yang, Yang
Zhang, Jianqi
Laursen, Bo W.
Lu, Kun
Wei, Zhixiang
Fluorination Induced Donor to Acceptor Transformation in A1–D–A2–D–A1-Type Photovoltaic Small Molecules
title Fluorination Induced Donor to Acceptor Transformation in A1–D–A2–D–A1-Type Photovoltaic Small Molecules
title_full Fluorination Induced Donor to Acceptor Transformation in A1–D–A2–D–A1-Type Photovoltaic Small Molecules
title_fullStr Fluorination Induced Donor to Acceptor Transformation in A1–D–A2–D–A1-Type Photovoltaic Small Molecules
title_full_unstemmed Fluorination Induced Donor to Acceptor Transformation in A1–D–A2–D–A1-Type Photovoltaic Small Molecules
title_short Fluorination Induced Donor to Acceptor Transformation in A1–D–A2–D–A1-Type Photovoltaic Small Molecules
title_sort fluorination induced donor to acceptor transformation in a1–d–a2–d–a1-type photovoltaic small molecules
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6127638/
https://www.ncbi.nlm.nih.gov/pubmed/30234102
http://dx.doi.org/10.3389/fchem.2018.00384
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