Benzo[4,5]cyclohepta[1,2-b]fluorene: an isomeric motif for pentacene containing linearly fused five-, six- and seven-membered rings
dc.contributor.author | Yang, Xuejin | |
dc.contributor.author | Shi, Xueliang | |
dc.contributor.author | Aratani, Naoki | |
dc.contributor.author | Goncalves, Theo | |
dc.contributor.author | Huang, Kuo-Wei | |
dc.contributor.author | Yamada, Hiroko | |
dc.contributor.author | Chi, Chunyan | |
dc.contributor.author | Miao, Qian | |
dc.date.accessioned | 2016-06-14T08:59:34Z | |
dc.date.available | 2016-06-14T08:59:34Z | |
dc.date.issued | 2016 | |
dc.identifier.citation | Benzo[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.issn | 2041-6520 | |
dc.identifier.issn | 2041-6539 | |
dc.identifier.doi | 10.1039/C6SC01795A | |
dc.identifier.uri | http://hdl.handle.net/10754/612971 | |
dc.description.abstract | Benzo[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.sponsorship | We 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.iso | en | |
dc.publisher | Royal Society of Chemistry (RSC) | |
dc.relation.url | http://pubs.rsc.org/en/Content/ArticleLanding/2016/SC/C6SC01795A | |
dc.rights | This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. http://creativecommons.org/licenses/by/3.0/ | |
dc.title | Benzo[4,5]cyclohepta[1,2-b]fluorene: an isomeric motif for pentacene containing linearly fused five-, six- and seven-membered rings | |
dc.type | Article | |
dc.contributor.department | Chemical Science Program | |
dc.contributor.department | Homogeneous Catalysis Laboratory (HCL) | |
dc.contributor.department | KAUST Catalysis Center (KCC) | |
dc.contributor.department | Physical Science and Engineering (PSE) Division | |
dc.identifier.journal | Chemical Science | |
dc.eprint.version | Post-print | |
dc.contributor.institution | Department of Chemistry, the Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China | |
dc.contributor.institution | Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore | |
dc.contributor.institution | Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5 Takayama-cho, Ikoma 630-0192, Japan | |
dc.contributor.affiliation | King Abdullah University of Science and Technology (KAUST) | |
kaust.person | Goncalves, Theo | |
kaust.person | Huang, Kuo-Wei | |
dc.relation.issupplementedby | DOI:10.5517/ccdc.csd.cc1l9jr5 | |
dc.relation.issupplementedby | DOI:10.5517/ccdc.csd.cc1l9jq4 | |
refterms.dateFOA | 2018-06-13T16:06:10Z | |
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> |
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