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Enhancement of charge transport properties of small molecule semiconductors by controlling fluorine substitution and effects on photovoltaic properties of organic solar cells and perovskite solar cells

We prepared a series of small molecules based on 7,7′-(4,4-bis(2-ethylhexyl)-4H-silolo[3,2-b:4,5-b′]dithiophene-2,6-diyl)bis(4-(5′-hexyl-[2,2′-bithiophene]-5-yl)benzo[c][1,2,5]thiadiazole) with different fluorine substitution patterns (0F–4F). Depending on symmetricity and numbers of fluorine atoms...

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Autores principales: Yun, Jae Hoon, Park, Sungmin, Heo, Jin Hyuck, Lee, Hyo-Sang, Yoon, Seongwon, Kang, Jinback, Im, Sang Hyuk, Kim, Hyunjung, Lee, Wonmok, Kim, BongSoo, Ko, Min Jae, Chung, Dae Sung, Son, Hae Jung
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5450529/
https://www.ncbi.nlm.nih.gov/pubmed/28567255
http://dx.doi.org/10.1039/c6sc02448c
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author Yun, Jae Hoon
Park, Sungmin
Heo, Jin Hyuck
Lee, Hyo-Sang
Yoon, Seongwon
Kang, Jinback
Im, Sang Hyuk
Kim, Hyunjung
Lee, Wonmok
Kim, BongSoo
Ko, Min Jae
Chung, Dae Sung
Son, Hae Jung
author_facet Yun, Jae Hoon
Park, Sungmin
Heo, Jin Hyuck
Lee, Hyo-Sang
Yoon, Seongwon
Kang, Jinback
Im, Sang Hyuk
Kim, Hyunjung
Lee, Wonmok
Kim, BongSoo
Ko, Min Jae
Chung, Dae Sung
Son, Hae Jung
author_sort Yun, Jae Hoon
collection PubMed
description We prepared a series of small molecules based on 7,7′-(4,4-bis(2-ethylhexyl)-4H-silolo[3,2-b:4,5-b′]dithiophene-2,6-diyl)bis(4-(5′-hexyl-[2,2′-bithiophene]-5-yl)benzo[c][1,2,5]thiadiazole) with different fluorine substitution patterns (0F–4F). Depending on symmetricity and numbers of fluorine atoms incorporated in the benzo[c][1,2,5]thiadiazole unit, they show very different optical and morphological properties in a film. 2F and 4F, which featured symmetric and even-numbered fluorine substitution patterns, display improved molecular packing structures and higher crystalline properties in a film compared with 1F and 3F and thus, 2F achieved the highest OTFT mobility, which is followed by 4F. In the bulk heterojunction solar cell fabricated with PC(71)BM, 2F achieves the highest photovoltaic performance with an 8.14% efficiency and 0F shows the lowest efficiency of 1.28%. Moreover, the planar-type perovskite solar cell (PSC) prepared with 2F as a dopant-free hole transport material shows a high power conversion efficiency of 14.5% due to its high charge transporting properties, which were significantly improved compared with the corresponding PSC device obtained from 0F (8.5%). From the studies, it is demonstrated that low variation in the local dipole moment and the narrow distribution of 2F conformers make intermolecular interactions favorable, which may effectively drive crystal formations in the solid state and thus, higher charge transport properties compared with 1F and 3F.
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spelling pubmed-54505292017-05-31 Enhancement of charge transport properties of small molecule semiconductors by controlling fluorine substitution and effects on photovoltaic properties of organic solar cells and perovskite solar cells Yun, Jae Hoon Park, Sungmin Heo, Jin Hyuck Lee, Hyo-Sang Yoon, Seongwon Kang, Jinback Im, Sang Hyuk Kim, Hyunjung Lee, Wonmok Kim, BongSoo Ko, Min Jae Chung, Dae Sung Son, Hae Jung Chem Sci Chemistry We prepared a series of small molecules based on 7,7′-(4,4-bis(2-ethylhexyl)-4H-silolo[3,2-b:4,5-b′]dithiophene-2,6-diyl)bis(4-(5′-hexyl-[2,2′-bithiophene]-5-yl)benzo[c][1,2,5]thiadiazole) with different fluorine substitution patterns (0F–4F). Depending on symmetricity and numbers of fluorine atoms incorporated in the benzo[c][1,2,5]thiadiazole unit, they show very different optical and morphological properties in a film. 2F and 4F, which featured symmetric and even-numbered fluorine substitution patterns, display improved molecular packing structures and higher crystalline properties in a film compared with 1F and 3F and thus, 2F achieved the highest OTFT mobility, which is followed by 4F. In the bulk heterojunction solar cell fabricated with PC(71)BM, 2F achieves the highest photovoltaic performance with an 8.14% efficiency and 0F shows the lowest efficiency of 1.28%. Moreover, the planar-type perovskite solar cell (PSC) prepared with 2F as a dopant-free hole transport material shows a high power conversion efficiency of 14.5% due to its high charge transporting properties, which were significantly improved compared with the corresponding PSC device obtained from 0F (8.5%). From the studies, it is demonstrated that low variation in the local dipole moment and the narrow distribution of 2F conformers make intermolecular interactions favorable, which may effectively drive crystal formations in the solid state and thus, higher charge transport properties compared with 1F and 3F. Royal Society of Chemistry 2016-11-01 2016-07-27 /pmc/articles/PMC5450529/ /pubmed/28567255 http://dx.doi.org/10.1039/c6sc02448c Text en This journal is © The Royal Society of Chemistry 2016 http://creativecommons.org/licenses/by-nc/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution-NonCommercial 3.0 Unported License (http://creativecommons.org/licenses/by-nc/3.0/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Yun, Jae Hoon
Park, Sungmin
Heo, Jin Hyuck
Lee, Hyo-Sang
Yoon, Seongwon
Kang, Jinback
Im, Sang Hyuk
Kim, Hyunjung
Lee, Wonmok
Kim, BongSoo
Ko, Min Jae
Chung, Dae Sung
Son, Hae Jung
Enhancement of charge transport properties of small molecule semiconductors by controlling fluorine substitution and effects on photovoltaic properties of organic solar cells and perovskite solar cells
title Enhancement of charge transport properties of small molecule semiconductors by controlling fluorine substitution and effects on photovoltaic properties of organic solar cells and perovskite solar cells
title_full Enhancement of charge transport properties of small molecule semiconductors by controlling fluorine substitution and effects on photovoltaic properties of organic solar cells and perovskite solar cells
title_fullStr Enhancement of charge transport properties of small molecule semiconductors by controlling fluorine substitution and effects on photovoltaic properties of organic solar cells and perovskite solar cells
title_full_unstemmed Enhancement of charge transport properties of small molecule semiconductors by controlling fluorine substitution and effects on photovoltaic properties of organic solar cells and perovskite solar cells
title_short Enhancement of charge transport properties of small molecule semiconductors by controlling fluorine substitution and effects on photovoltaic properties of organic solar cells and perovskite solar cells
title_sort enhancement of charge transport properties of small molecule semiconductors by controlling fluorine substitution and effects on photovoltaic properties of organic solar cells and perovskite solar cells
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5450529/
https://www.ncbi.nlm.nih.gov/pubmed/28567255
http://dx.doi.org/10.1039/c6sc02448c
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