Molecular Engineering of Non-Halogenated Solution-Processable Bithiazole based Electron Transport Polymeric Semiconductors

Handle URI:
http://hdl.handle.net/10754/350202
Title:
Molecular Engineering of Non-Halogenated Solution-Processable Bithiazole based Electron Transport Polymeric Semiconductors
Authors:
Fu, Boyi; Wang, Cheng-Yin; Rose, Bradley Daniel ( 0000-0002-1774-3981 ) ; Jiang, Yundi; Chang, Mincheol; Chu, Ping-Hsun; Yuan, Zhibo; Fuentes-Hernandez, Canek; Bernard, Kippelen; Bredas, Jean-Luc ( 0000-0001-7278-4471 ) ; Collard, David M.; Reichmanis, Elsa
Abstract:
The electron deficiency and trans planar conformation of bithiazole is potentially beneficial for the electron transport performance of organic semiconductors. However, the incorporation of bithiazole into polymers through a facile synthetic strategy remains a challenge. Herein, 2,2’-bithiazole was synthesized in one step and copolymerized with dithienyldiketopyrrolopyrrole to afford poly(dithienyldiketopyrrolopyrrole-bithiazole), PDBTz. PDBTz exhibited electron mobility reaching 0.3 cm2V-1s-1 in organic field-effect transistor (OFET) configuration; this contrasts with a recently discussed isoelectronic conjugated polymer comprising an electron rich bithiophene and dithienyldiketopyrrolopyrrole, which displays merely hole transport characteristics. This inversion of charge carrier transport characteristics confirms the significant potential for bithiazole in the development of electron transport semiconducting materials. Branched 5-decylheptacyl side chains were incorporated into PDBTz to enhance polymer solubility, particularly in non-halogenated, more environmentally compatible solvents. PDBTz cast from a range of non-halogenated solvents exhibited film morphologies and field-effect electron mobility similar to those cast from halogenated solvents.
KAUST Department:
Solar and Photovoltaic Engineering Research Center
Citation:
Molecular Engineering of Non-Halogenated Solution-Processable Bithiazole based Electron Transport Polymeric Semiconductors 2015:150401105405000 Chemistry of Materials
Publisher:
American Chemical Society (ACS)
Journal:
Chemistry of Materials
Issue Date:
1-Apr-2015
DOI:
10.1021/acs.chemmater.5b00173
Type:
Article
ISSN:
0897-4756; 1520-5002
Additional Links:
http://pubs.acs.org/doi/abs/10.1021/acs.chemmater.5b00173
Appears in Collections:
Articles; Solar and Photovoltaic Engineering Research Center (SPERC)

Full metadata record

DC FieldValue Language
dc.contributor.authorFu, Boyien
dc.contributor.authorWang, Cheng-Yinen
dc.contributor.authorRose, Bradley Danielen
dc.contributor.authorJiang, Yundien
dc.contributor.authorChang, Mincheolen
dc.contributor.authorChu, Ping-Hsunen
dc.contributor.authorYuan, Zhiboen
dc.contributor.authorFuentes-Hernandez, Caneken
dc.contributor.authorBernard, Kippelenen
dc.contributor.authorBredas, Jean-Lucen
dc.contributor.authorCollard, David M.en
dc.contributor.authorReichmanis, Elsaen
dc.date.accessioned2015-04-08T12:28:49Zen
dc.date.available2015-04-08T12:28:49Zen
dc.date.issued2015-04-01en
dc.identifier.citationMolecular Engineering of Non-Halogenated Solution-Processable Bithiazole based Electron Transport Polymeric Semiconductors 2015:150401105405000 Chemistry of Materialsen
dc.identifier.issn0897-4756en
dc.identifier.issn1520-5002en
dc.identifier.doi10.1021/acs.chemmater.5b00173en
dc.identifier.urihttp://hdl.handle.net/10754/350202en
dc.description.abstractThe electron deficiency and trans planar conformation of bithiazole is potentially beneficial for the electron transport performance of organic semiconductors. However, the incorporation of bithiazole into polymers through a facile synthetic strategy remains a challenge. Herein, 2,2’-bithiazole was synthesized in one step and copolymerized with dithienyldiketopyrrolopyrrole to afford poly(dithienyldiketopyrrolopyrrole-bithiazole), PDBTz. PDBTz exhibited electron mobility reaching 0.3 cm2V-1s-1 in organic field-effect transistor (OFET) configuration; this contrasts with a recently discussed isoelectronic conjugated polymer comprising an electron rich bithiophene and dithienyldiketopyrrolopyrrole, which displays merely hole transport characteristics. This inversion of charge carrier transport characteristics confirms the significant potential for bithiazole in the development of electron transport semiconducting materials. Branched 5-decylheptacyl side chains were incorporated into PDBTz to enhance polymer solubility, particularly in non-halogenated, more environmentally compatible solvents. PDBTz cast from a range of non-halogenated solvents exhibited film morphologies and field-effect electron mobility similar to those cast from halogenated solvents.en
dc.publisherAmerican Chemical Society (ACS)en
dc.relation.urlhttp://pubs.acs.org/doi/abs/10.1021/acs.chemmater.5b00173en
dc.rightsArchived with thanks to Chemistry of Materialsen
dc.titleMolecular Engineering of Non-Halogenated Solution-Processable Bithiazole based Electron Transport Polymeric Semiconductorsen
dc.typeArticleen
dc.contributor.departmentSolar and Photovoltaic Engineering Research Centeren
dc.identifier.journalChemistry of Materialsen
dc.eprint.versionPost-printen
dc.contributor.institutionSchool of Chemical & Biomolecular Engineering, Geor gia Institute of Technology, 311 Ferst Drive, Atlanta, GA 30332-0100, U.S.Aen
dc.contributor.institutionSchool of Electrical and Computer Engineering, Geor gia Institute of Technology, 777 Atlantic Dr NW, Atlanta, GA 30332-0250, U.S.Aen
dc.contributor.institutionSchool of Chemistry & Biochemistry, Georgia Institu te of Technology, 901 Atlantic Drive, Atlanta, GA 30332-0400, U.S.Aen
dc.contributor.institutionSchool of Materials Science and Engineering, Georgi a Institute of Technology, 771 Ferst Drive, Atlanta, GA 30332-0245, U.S.A.en
kaust.authorRose, Bradley Danielen
kaust.authorBredas, Jean-Lucen
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