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Title: Benzo[4,5]cyclohepta[1,2-: B] fluorene: An isomeric motif for pentacene containing linearly fused five-, six- and seven-membered rings
Authors: Yang, X
Shi, X 
Aratani, N
Gonçalves, T.P
Huang, K.-W
Yamada, H
Chi, C 
Miao, Q
Keywords: Absorption spectroscopy
Chemical analysis
Cyclic voltammetry
Field effect transistors
Thin film transistors
X ray crystallography
Electronic absorption spectroscopy
Field-effect mobilities
p-Type organic semiconductors
Polycyclic hydrocarbon
Seven-membered rings
Six-membered rings
X-ray crystallographic analysis
Semiconducting organic compounds
Issue Date: 2016
Publisher: Royal Society of Chemistry
Citation: Yang, X, Shi, X, Aratani, N, Gonçalves, T.P, Huang, K.-W, Yamada, H, Chi, C, Miao, Q (2016). Benzo[4,5]cyclohepta[1,2-: B] fluorene: An isomeric motif for pentacene containing linearly fused five-, six- and seven-membered rings. Chemical Science 7 (9) : 6176-6181. ScholarBank@NUS Repository.
Abstract: Benzo[4,5]cyclohepta[1,2-b]fluorene (5a), a new ?-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 ? 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 . © The Royal Society of Chemistry 2016.
Source Title: Chemical Science
ISSN: 20416520
DOI: 10.1039/c6sc01795a
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