Benzo[4,5]cyclohepta[1,2-b]fluorene: an isomeric motif for pentacene containing linearly fused five-, six- and seven-membered rings
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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.
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.
SponsorsWe 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.
PublisherRoyal Society of Chemistry (RSC)
Is Supplemented ByYang, 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
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