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 (C₆-C₅-C₆-C₇-C₆), 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 cm² V^-1 s^-1.

SUBMITTER: Yang X 

PROVIDER: S-EPMC6024176 | biostudies-literature | 2016 Sep

REPOSITORIES: biostudies-literature