Thienoacene-fused pentalenes: Syntheses, structures, physical properties and applications for organic field-effect transistors

Handle URI:
http://hdl.handle.net/10754/563875
Title:
Thienoacene-fused pentalenes: Syntheses, structures, physical properties and applications for organic field-effect transistors
Authors:
Dai, Gaole; Chang, Jingjing; Shi, Xueliang; Zhang, Wenhua; Zheng, Bin; Huang, Kuo-Wei ( 0000-0003-1900-2658 ) ; Chi, Chunyan
Abstract:
Three soluble and stable thienoacene-fused pentalene derivatives (1-3) with different π-conjugation lengths were synthesized. X-ray crystallographic analysis and density functional theory (DFT) calculations revealed their unique geometric and electronic structures due to the interaction between the aromatic thienoacene units and antiaromatic pentalene moiety. As a result, they all possess a small energy gap and show amphoteric redox behaviour. Time dependent (TD) DFT calculations were used to explain their unique electronic absorption spectra. These new compounds exhibited good thermal stability and ordered packing in solid state and thus their applications in organic field-effect transistors (OFETs) were also investigated. The highest field-effect hole mobility of 0.016, 0.036 and 0.001 cm2 V-1 s-1 was achieved for solution-processed thin films of 1-3, respectively.
KAUST Department:
KAUST Catalysis Center (KCC); Physical Sciences and Engineering (PSE) Division; Chemical Science Program; HCL
Publisher:
Wiley-Blackwell
Journal:
Chemistry - A European Journal
Issue Date:
27-Nov-2014
DOI:
10.1002/chem.201405652
Type:
Article
ISSN:
09476539
Sponsors:
C.C. acknowledges financial support from MOE AcRF Tier 1 grants R-143-000-510-112, R-143-000-573-112 and NUS start up grant R-143-000-486-133. K.W.H. acknowledges financial support from KAUST.
Is Supplemented By:
Dai, G., Chang, J., Shi, X., Zhang, W., Zheng, B., Huang, K.-W., & Chi, C. (2014). CCDC 1003816: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc12pk5h; DOI:10.5517/cc12pk5h; HANDLE:http://hdl.handle.net/10754/624320; Dai, G., Chang, J., Shi, X., Zhang, W., Zheng, B., Huang, K.-W., & Chi, C. (2014). CCDC 1003817: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc12pk6j; DOI:10.5517/cc12pk6j; HANDLE:http://hdl.handle.net/10754/624321
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorDai, Gaoleen
dc.contributor.authorChang, Jingjingen
dc.contributor.authorShi, Xueliangen
dc.contributor.authorZhang, Wenhuaen
dc.contributor.authorZheng, Binen
dc.contributor.authorHuang, Kuo-Weien
dc.contributor.authorChi, Chunyanen
dc.date.accessioned2015-08-03T12:17:55Zen
dc.date.available2015-08-03T12:17:55Zen
dc.date.issued2014-11-27en
dc.identifier.issn09476539en
dc.identifier.doi10.1002/chem.201405652en
dc.identifier.urihttp://hdl.handle.net/10754/563875en
dc.description.abstractThree soluble and stable thienoacene-fused pentalene derivatives (1-3) with different π-conjugation lengths were synthesized. X-ray crystallographic analysis and density functional theory (DFT) calculations revealed their unique geometric and electronic structures due to the interaction between the aromatic thienoacene units and antiaromatic pentalene moiety. As a result, they all possess a small energy gap and show amphoteric redox behaviour. Time dependent (TD) DFT calculations were used to explain their unique electronic absorption spectra. These new compounds exhibited good thermal stability and ordered packing in solid state and thus their applications in organic field-effect transistors (OFETs) were also investigated. The highest field-effect hole mobility of 0.016, 0.036 and 0.001 cm2 V-1 s-1 was achieved for solution-processed thin films of 1-3, respectively.en
dc.description.sponsorshipC.C. acknowledges financial support from MOE AcRF Tier 1 grants R-143-000-510-112, R-143-000-573-112 and NUS start up grant R-143-000-486-133. K.W.H. acknowledges financial support from KAUST.en
dc.publisherWiley-Blackwellen
dc.subjectField-effect transistorsen
dc.subjectPentaleneen
dc.subjectPi-conjugated systemsen
dc.subjectSemiconductorsen
dc.subjectThienoaceneen
dc.titleThienoacene-fused pentalenes: Syntheses, structures, physical properties and applications for organic field-effect transistorsen
dc.typeArticleen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentHCLen
dc.identifier.journalChemistry - A European Journalen
dc.contributor.institutionDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, Singaporeen
dc.contributor.institutionInstitute of Materials Research and Engineering, ASTAR 3 Research Link, Singaporeen
kaust.authorZheng, Binen
kaust.authorHuang, Kuo-Weien
dc.relation.isSupplementedByDai, G., Chang, J., Shi, X., Zhang, W., Zheng, B., Huang, K.-W., & Chi, C. (2014). CCDC 1003816: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc12pk5hen
dc.relation.isSupplementedByDOI:10.5517/cc12pk5hen
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624320en
dc.relation.isSupplementedByDai, G., Chang, J., Shi, X., Zhang, W., Zheng, B., Huang, K.-W., & Chi, C. (2014). CCDC 1003817: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc12pk6jen
dc.relation.isSupplementedByDOI:10.5517/cc12pk6jen
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624321en
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