Fluorinated Head-to-Head Dialkoxybithiophene: A New Electron-Donating Building Block for High-Performance Polymer Semiconductors
DC Field | Value | Language |
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dc.contributor.author | Huang, Jun | - |
dc.contributor.author | Guo, Han | - |
dc.contributor.author | Uddin, Mohammad Afsar | - |
dc.contributor.author | Yu, Jianwei | - |
dc.contributor.author | Woo, Han Young | - |
dc.contributor.author | Guo, Xugang | - |
dc.date.accessioned | 2021-09-02T13:59:02Z | - |
dc.date.available | 2021-09-02T13:59:02Z | - |
dc.date.created | 2021-06-16 | - |
dc.date.issued | 2018-03 | - |
dc.identifier.issn | 2199-160X | - |
dc.identifier.uri | https://scholar.korea.ac.kr/handle/2021.sw.korea/76815 | - |
dc.description.abstract | New building blocks with good solubility and optimized optoelectrical property are critical for materials development in organic electronics. Herein, a new head-to-head linkage containing a donor unit, 4,4'-difluoro-3,3'-dialkoxy-2,2'-bithiophene (BTfOR), is synthesized. The dialkoxy chains afford good materials solubility and also planar backbone via noncovalent (thienyl) S.(alkoxy) O interactions. Compared to the reported 3,3'-dialkoxy-2,2'-bithiophene (BTOR), F addition leads to BTfOR with lower-lying frontier molecular orbitals and can further promote polymer packing via additional F ... S or F ... H interactions. BTfOR can be readily stannylated to afford tin monomer with high purity and excellent reactivity toward Stille polymerization. As a proof of concept for materials design, BTfOR-based homopolymer (PBTfOR) is synthesized, showing high molecular weight and strong aggregation. Moreover, the HOMO (-4.98 eV) of PBTfOR is greatly lower than that (-4.54 eV) of nonfluorinated counterpart PBTOR, which is attributed to the addition of F atoms. When incorporated into thin-film transistors, PBTfOR exhibits a remarkable hole mobility of 0.57 cm(2) V-1 s(-1), showing an exceptional example of high-mobility head-to-head polythiophene. This study demonstrates that introduction of F atoms can lead to BTfOR with optimized physicochemical properties, and the new BTfOR should find promising use for constructing donor-acceptor copolymers for high-performance electronic devices. | - |
dc.language | English | - |
dc.language.iso | en | - |
dc.publisher | WILEY | - |
dc.subject | CONJUGATED POLYMERS | - |
dc.subject | SOLAR-CELLS | - |
dc.subject | BACKBONE FLUORINATION | - |
dc.subject | CHARGE-TRANSPORT | - |
dc.subject | ORGANIC SEMICONDUCTORS | - |
dc.subject | RATIONAL DESIGN | - |
dc.subject | HIGH-MOBILITY | - |
dc.subject | THIN-FILMS | - |
dc.subject | BAND-GAP | - |
dc.subject | TRANSISTORS | - |
dc.title | Fluorinated Head-to-Head Dialkoxybithiophene: A New Electron-Donating Building Block for High-Performance Polymer Semiconductors | - |
dc.type | Article | - |
dc.contributor.affiliatedAuthor | Woo, Han Young | - |
dc.identifier.doi | 10.1002/aelm.201700519 | - |
dc.identifier.scopusid | 2-s2.0-85039156661 | - |
dc.identifier.wosid | 000427002100009 | - |
dc.identifier.bibliographicCitation | ADVANCED ELECTRONIC MATERIALS, v.4, no.3 | - |
dc.relation.isPartOf | ADVANCED ELECTRONIC MATERIALS | - |
dc.citation.title | ADVANCED ELECTRONIC MATERIALS | - |
dc.citation.volume | 4 | - |
dc.citation.number | 3 | - |
dc.type.rims | ART | - |
dc.type.docType | Article | - |
dc.description.journalClass | 1 | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
dc.relation.journalResearchArea | Science & Technology - Other Topics | - |
dc.relation.journalResearchArea | Materials Science | - |
dc.relation.journalResearchArea | Physics | - |
dc.relation.journalWebOfScienceCategory | Nanoscience & Nanotechnology | - |
dc.relation.journalWebOfScienceCategory | Materials Science, Multidisciplinary | - |
dc.relation.journalWebOfScienceCategory | Physics, Applied | - |
dc.subject.keywordPlus | CONJUGATED POLYMERS | - |
dc.subject.keywordPlus | SOLAR-CELLS | - |
dc.subject.keywordPlus | BACKBONE FLUORINATION | - |
dc.subject.keywordPlus | CHARGE-TRANSPORT | - |
dc.subject.keywordPlus | ORGANIC SEMICONDUCTORS | - |
dc.subject.keywordPlus | RATIONAL DESIGN | - |
dc.subject.keywordPlus | HIGH-MOBILITY | - |
dc.subject.keywordPlus | THIN-FILMS | - |
dc.subject.keywordPlus | BAND-GAP | - |
dc.subject.keywordPlus | TRANSISTORS | - |
dc.subject.keywordAuthor | fluorinated thiophenes | - |
dc.subject.keywordAuthor | head-to-head linkages | - |
dc.subject.keywordAuthor | noncovalent sulfuroxygen interactions | - |
dc.subject.keywordAuthor | organic thin-film transistors | - |
dc.subject.keywordAuthor | polythiophenes | - |
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