Benzo[4,5]cyclohepta[1,2-b]fluorene: an isomeric motif for pentacene containing linearly fused five-, six- and seven-membered rings

Xuejin Yang, Xueliang Shi, Naoki Aratani, Theo Goncalves, Kuo-Wei Huang, Hiroko Yamada, Chunyan Chi, Qian Miao

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

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.
Original languageEnglish (US)
Pages (from-to)6176-6181
Number of pages6
JournalChem. Sci.
Volume7
Issue number9
DOIs
StatePublished - 2016

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