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 pi-conjugated polycyclic hydrocarbon containing linearly fused six-, five-, six-, seven- and six-membered rings (C-6-C-5-C-6-C-7-C-6), was designed and its stable derivatives 5b and 5c were synthesized. With 22 pi 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 a field effect mobility of up to 0.025 cm(2) V-1 s(-1).
All Author(s) ListYang XJ, Shi XL, Aratani N, Goncalves TP, Huang KW, Yamada H, Chi CY, Miao Q
Journal nameChemical Science
Volume Number7
Issue Number9
Pages6176 - 6181
LanguagesEnglish-United Kingdom
Web of Science Subject CategoriesChemistry, Multidisciplinary;Chemistry

Last updated on 2020-29-10 at 01:25