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

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.