Benzo[4,5]cyclohepta[1,2-b]fluorene: an isomeric motif for pentacene containing linearly fused five-, six- and seven-membered rings
Type
ArticleAuthors
Yang, XuejinShi, Xueliang
Aratani, Naoki
Goncalves, Theo
Huang, Kuo-Wei

Yamada, Hiroko
Chi, Chunyan
Miao, Qian
KAUST Department
Chemical Science ProgramHomogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2016Permanent link to this record
http://hdl.handle.net/10754/612971
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Show full item recordAbstract
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.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.Sponsors
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.Publisher
Royal Society of Chemistry (RSC)Journal
Chemical ScienceAdditional Links
http://pubs.rsc.org/en/Content/ArticleLanding/2016/SC/C6SC01795ARelations
Is Supplemented By:- [Dataset]
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: 10.5517/ccdc.csd.cc1l9jr5 HANDLE: 10754/624575 - [Dataset]
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: 10.5517/ccdc.csd.cc1l9jq4 HANDLE: 10754/624574
ae974a485f413a2113503eed53cd6c53
10.1039/C6SC01795A