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“Disrupt and induce” intermolecular interactions to rationally design organic semiconductor crystals: from herringbone to rubrene-like pitched π-stacking

The packing structures of organic semiconductors in the solid state play critical roles in determining the performances of their optoelectronic devices, such as organic field-effect transistors (OFETs). It is a formidable challenge to rationally design molecular packing in the solid state owing to t...

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Autores principales: Wang, Chengyuan, Hashizume, Daisuke, Nakano, Masahiro, Ogaki, Takuya, Takenaka, Hiroyuki, Kawabata, Kohsuke, Takimiya, Kazuo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8148081/
https://www.ncbi.nlm.nih.gov/pubmed/34084388
http://dx.doi.org/10.1039/c9sc05902d
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author Wang, Chengyuan
Hashizume, Daisuke
Nakano, Masahiro
Ogaki, Takuya
Takenaka, Hiroyuki
Kawabata, Kohsuke
Takimiya, Kazuo
author_facet Wang, Chengyuan
Hashizume, Daisuke
Nakano, Masahiro
Ogaki, Takuya
Takenaka, Hiroyuki
Kawabata, Kohsuke
Takimiya, Kazuo
author_sort Wang, Chengyuan
collection PubMed
description The packing structures of organic semiconductors in the solid state play critical roles in determining the performances of their optoelectronic devices, such as organic field-effect transistors (OFETs). It is a formidable challenge to rationally design molecular packing in the solid state owing to the difficulty of controlling intermolecular interactions. Here we report a unique materials design strategy based on the β-methylthionation of acenedithiophenes to generally and selectively control the packing structures of materials to create organic semiconductors rivalling rubrene, a benchmark high-mobility material with a characteristic pitched π-stacking structure in the solid state. Furthermore, the effect of the β-methylthionation on the packing structure was analyzed by Hirshfeld surface analysis together with theoretical calculations based on symmetry-adapted perturbation theory (SAPT). The results clearly demonstrated that the β-methylthionation of acenedithiophenes can universally alter the intermolecular interactions by disrupting the favorable edge-to-face manner in the parent acenedithiophenes and simultaneously inducing face-to-face and end-to-face interactions in the β-methylthionated acenedithiophenes. This “disrupt and induce” strategy to manipulate intermolecular interactions can open a door to rational packing design based on the molecular structure.
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spelling pubmed-81480812021-06-02 “Disrupt and induce” intermolecular interactions to rationally design organic semiconductor crystals: from herringbone to rubrene-like pitched π-stacking Wang, Chengyuan Hashizume, Daisuke Nakano, Masahiro Ogaki, Takuya Takenaka, Hiroyuki Kawabata, Kohsuke Takimiya, Kazuo Chem Sci Chemistry The packing structures of organic semiconductors in the solid state play critical roles in determining the performances of their optoelectronic devices, such as organic field-effect transistors (OFETs). It is a formidable challenge to rationally design molecular packing in the solid state owing to the difficulty of controlling intermolecular interactions. Here we report a unique materials design strategy based on the β-methylthionation of acenedithiophenes to generally and selectively control the packing structures of materials to create organic semiconductors rivalling rubrene, a benchmark high-mobility material with a characteristic pitched π-stacking structure in the solid state. Furthermore, the effect of the β-methylthionation on the packing structure was analyzed by Hirshfeld surface analysis together with theoretical calculations based on symmetry-adapted perturbation theory (SAPT). The results clearly demonstrated that the β-methylthionation of acenedithiophenes can universally alter the intermolecular interactions by disrupting the favorable edge-to-face manner in the parent acenedithiophenes and simultaneously inducing face-to-face and end-to-face interactions in the β-methylthionated acenedithiophenes. This “disrupt and induce” strategy to manipulate intermolecular interactions can open a door to rational packing design based on the molecular structure. The Royal Society of Chemistry 2020-01-07 /pmc/articles/PMC8148081/ /pubmed/34084388 http://dx.doi.org/10.1039/c9sc05902d Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Wang, Chengyuan
Hashizume, Daisuke
Nakano, Masahiro
Ogaki, Takuya
Takenaka, Hiroyuki
Kawabata, Kohsuke
Takimiya, Kazuo
“Disrupt and induce” intermolecular interactions to rationally design organic semiconductor crystals: from herringbone to rubrene-like pitched π-stacking
title “Disrupt and induce” intermolecular interactions to rationally design organic semiconductor crystals: from herringbone to rubrene-like pitched π-stacking
title_full “Disrupt and induce” intermolecular interactions to rationally design organic semiconductor crystals: from herringbone to rubrene-like pitched π-stacking
title_fullStr “Disrupt and induce” intermolecular interactions to rationally design organic semiconductor crystals: from herringbone to rubrene-like pitched π-stacking
title_full_unstemmed “Disrupt and induce” intermolecular interactions to rationally design organic semiconductor crystals: from herringbone to rubrene-like pitched π-stacking
title_short “Disrupt and induce” intermolecular interactions to rationally design organic semiconductor crystals: from herringbone to rubrene-like pitched π-stacking
title_sort “disrupt and induce” intermolecular interactions to rationally design organic semiconductor crystals: from herringbone to rubrene-like pitched π-stacking
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8148081/
https://www.ncbi.nlm.nih.gov/pubmed/34084388
http://dx.doi.org/10.1039/c9sc05902d
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