Dianthraceno[a,e]pentalenes: Synthesis, crystallographic structures and applications in organic field-effect transistors

Handle URI:
http://hdl.handle.net/10754/563934
Title:
Dianthraceno[a,e]pentalenes: Synthesis, crystallographic structures and applications in organic field-effect transistors
Authors:
Dai, Gaole; Chang, Jingjing; Zhang, Wenhua; Bai, Shiqiang; Huang, Kuo-Wei ( 0000-0003-1900-2658 ) ; Xu, Jianwei; Chi, Chunyan
Abstract:
Two soluble and stable dianthraceno[a,e]pentalenes with two (DAP1) and six (DAP2) phenyl substituents were synthesized. Both compounds possess a small energy band gap and show amphoteric redox behaviour due to intramolecular donor-accepter interactions. X-ray crystallographic analysis revealed that DAP2 has a closely packed structure with multi-dimensional [C-H⋯π] interactions although there are no π-π interactions between the dianthraceno[a,e]pentalene cores. As a result, solution-processed field effect transistors based on DAP2 exhibited an average hole mobility of 0.65 cm2 V-1 s-1. Under similar conditions, DAP1 showed an average field effect hole mobility of 0.001 cm2 V-1 s-1. This journal is
KAUST Department:
KAUST Catalysis Center (KCC); Physical Sciences and Engineering (PSE) Division; Chemical Science Program; HCL
Publisher:
Royal Society of Chemistry (RSC)
Journal:
Chem. Commun.
Issue Date:
2015
DOI:
10.1039/c4cc07630c
Type:
Article
ISSN:
13597345
Sponsors:
This work was financially supported by the NUS Start-Up Grant (R-143-000-486-133) and MOE AcRF grants (R-143-000510-112 and R-143-000-573-112) (C. C.), the NUS-IMRE Molecular Material Center (J. X.), and KAUST (K. W. H.).
Is Supplemented By:
Dai, G., Chang, J., Zhang, W., Bai, S., Huang, K.-W., Xu, J., & Chi, C. (2014). CCDC 1008484: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc12vdr2; DOI:10.5517/cc12vdr2; HANDLE:http://hdl.handle.net/10754/624338; Dai, G., Chang, J., Zhang, W., Bai, S., Huang, K.-W., Xu, J., & Chi, C. (2014). CCDC 1008483: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc12vdq1; DOI:10.5517/cc12vdq1; HANDLE:http://hdl.handle.net/10754/624337
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.authorZhang, Wenhuaen
dc.contributor.authorBai, Shiqiangen
dc.contributor.authorHuang, Kuo-Weien
dc.contributor.authorXu, Jianweien
dc.contributor.authorChi, Chunyanen
dc.date.accessioned2015-08-03T12:20:04Zen
dc.date.available2015-08-03T12:20:04Zen
dc.date.issued2015en
dc.identifier.issn13597345en
dc.identifier.doi10.1039/c4cc07630cen
dc.identifier.urihttp://hdl.handle.net/10754/563934en
dc.description.abstractTwo soluble and stable dianthraceno[a,e]pentalenes with two (DAP1) and six (DAP2) phenyl substituents were synthesized. Both compounds possess a small energy band gap and show amphoteric redox behaviour due to intramolecular donor-accepter interactions. X-ray crystallographic analysis revealed that DAP2 has a closely packed structure with multi-dimensional [C-H⋯π] interactions although there are no π-π interactions between the dianthraceno[a,e]pentalene cores. As a result, solution-processed field effect transistors based on DAP2 exhibited an average hole mobility of 0.65 cm2 V-1 s-1. Under similar conditions, DAP1 showed an average field effect hole mobility of 0.001 cm2 V-1 s-1. This journal isen
dc.description.sponsorshipThis work was financially supported by the NUS Start-Up Grant (R-143-000-486-133) and MOE AcRF grants (R-143-000510-112 and R-143-000-573-112) (C. C.), the NUS-IMRE Molecular Material Center (J. X.), and KAUST (K. W. H.).en
dc.publisherRoyal Society of Chemistry (RSC)en
dc.titleDianthraceno[a,e]pentalenes: Synthesis, crystallographic structures and applications in 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.journalChem. Commun.en
dc.contributor.institutionDepartment of Chemistry, National University of Singapore, 3 Science Drive 3Singapore, Singaporeen
dc.contributor.institutionInstitute of Materials Research and Engineering, 3 Research LinkSingapore, Singaporeen
kaust.authorHuang, Kuo-Weien
dc.relation.isSupplementedByDai, G., Chang, J., Zhang, W., Bai, S., Huang, K.-W., Xu, J., & Chi, C. (2014). CCDC 1008484: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc12vdr2en
dc.relation.isSupplementedByDOI:10.5517/cc12vdr2en
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624338en
dc.relation.isSupplementedByDai, G., Chang, J., Zhang, W., Bai, S., Huang, K.-W., Xu, J., & Chi, C. (2014). CCDC 1008483: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc12vdq1en
dc.relation.isSupplementedByDOI:10.5517/cc12vdq1en
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624337en
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