Show simple item record

dc.contributor.authorYang, Xuejin
dc.contributor.authorShi, Xueliang
dc.contributor.authorAratani, Naoki
dc.contributor.authorGoncalves, Theo
dc.contributor.authorHuang, Kuo-Wei
dc.contributor.authorYamada, Hiroko
dc.contributor.authorChi, Chunyan
dc.contributor.authorMiao, Qian
dc.date.accessioned2016-06-14T08:59:34Z
dc.date.available2016-06-14T08:59:34Z
dc.date.issued2016
dc.identifier.citationBenzo[4,5]cyclohepta[1,2-b]fluorene: an isomeric motif for pentacene containing linearly fused five-, six- and seven-membered rings 2016 Chem. Sci.
dc.identifier.issn2041-6520
dc.identifier.issn2041-6539
dc.identifier.doi10.1039/C6SC01795A
dc.identifier.urihttp://hdl.handle.net/10754/612971
dc.description.abstractBenzo[4,5]cyclohepta[1,2-b]fluorene (5a), a new π-conjugated polycyclic hydrocarbon containing linearly fused six-, five-, six-, seven- and six-membered rings (C6-C5-C6-C7-C6), was designed and its stable derivatives 5b and 5c were synthesized. With 22 π electrons, 5a is an isomer of pentacene with quinoidal, dipolar ionic and diradical resonance forms. Molecules 5b and 5c were experimentally investigated with cyclic voltammetry, electronic absorption spectroscopy and X-ray crystallographic analysis, and theoretically studied by calculating the NICS value, diradical character and dipole moment. A comparison of 5a–c with pentacene and other pentacene analogues containing linearly fused five- or seven- membered rings was also conducted and discussed. It was found that 5b behaved as a p-type organic semiconductor in solution-processed thin film transistors with field effect mobility of up to 0.025 cm2/Vs.
dc.description.sponsorshipWe are grateful to Prof. Michael M. Haley (University of Oregon) and Prof. Yoshito Tobe (Osaka University) for their kind support and helpful discussion. X. Yang and Q. Miao thank financial support from the Research Grants Council of Hong Kong (project number: GRF402412, CRF C4030-14G). X. Shi and C. Chi thank financial support from MOE Tier 1 grant (R-143- 000-623-112), Tier 2 grant (MOE2014-T2-1-080) and Tier 3 programme (MOE2014-T3-1-004). N. Aratani and H. Yamada thank support from the Grants-in-Aid for Scientific Research from JSPS (Nos. 16H02286, 26105004 and 26288038) and CREST, JST. T. P. Gonçalves and K.-W. Huang acknowledge the financial support from KAUST.
dc.language.isoen
dc.publisherRoyal Society of Chemistry (RSC)
dc.relation.urlhttp://pubs.rsc.org/en/Content/ArticleLanding/2016/SC/C6SC01795A
dc.rightsThis article is licensed under a Creative Commons Attribution 3.0 Unported Licence. http://creativecommons.org/licenses/by/3.0/
dc.titleBenzo[4,5]cyclohepta[1,2-b]fluorene: an isomeric motif for pentacene containing linearly fused five-, six- and seven-membered rings
dc.typeArticle
dc.contributor.departmentChemical Science Program
dc.contributor.departmentHomogeneous Catalysis Laboratory (HCL)
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.identifier.journalChemical Science
dc.eprint.versionPost-print
dc.contributor.institutionDepartment of Chemistry, the Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China
dc.contributor.institutionDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore
dc.contributor.institutionGraduate School of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5 Takayama-cho, Ikoma 630-0192, Japan
dc.contributor.affiliationKing Abdullah University of Science and Technology (KAUST)
kaust.personGoncalves, Theo
kaust.personHuang, Kuo-Wei
dc.relation.issupplementedbyDOI:10.5517/ccdc.csd.cc1l9jr5
dc.relation.issupplementedbyDOI:10.5517/ccdc.csd.cc1l9jq4
refterms.dateFOA2018-06-13T16:06:10Z
display.relations<b> Is Supplemented By:</b> <br/> <ul><li><i>[Dataset]</i> <br/> Yang, X., Shi, X., Aratani, N., Gonçalves, T. P., Huang, K.-W., Yamada, H., … Miao, Q. (2016). CCDC 1468927: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1l9jr5. DOI: <a href="https://doi.org/10.5517/ccdc.csd.cc1l9jr5">10.5517/ccdc.csd.cc1l9jr5</a> HANDLE: <a href="http://hdl.handle.net/10754/624575">10754/624575</a></li><li><i>[Dataset]</i> <br/> Yang, X., Shi, X., Aratani, N., Gonçalves, T. P., Huang, K.-W., Yamada, H., … Miao, Q. (2016). CCDC 1468926: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1l9jq4. DOI: <a href="https://doi.org/10.5517/ccdc.csd.cc1l9jq4">10.5517/ccdc.csd.cc1l9jq4</a> HANDLE: <a href="http://hdl.handle.net/10754/624574">10754/624574</a></li></ul>


Files in this item

Thumbnail
Name:
c6sc01795a.pdf
Size:
1.291Mb
Format:
PDF
Description:
Accepted Manuscript
Thumbnail
Name:
c6sc01795a1.pdf
Size:
4.972Mb
Format:
PDF
Description:
Supplemental files
Thumbnail
Name:
c6sc01795a2.cif
Size:
1.240Mb
Format:
Unknown
Description:
Supplemental files

This item appears in the following Collection(s)

Show simple item record