Wiley, Angewandte Chemie, 48(127), p. 14620-14624, 2015
Wiley, Angewandte Chemie International Edition, 48(54), p. 14412-14416, 2015
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Quinoidal thia-acene analogues, as the respective isoelectronic structures of pentacene and nonacene, were synthesized and an unusual 1,2-sulfur migration was observed during the Friedel-Crafts alkylation reaction. The analogues display a closed-shell quinoidal structure in the ground state with a distinctive dipolar character. In contrast to their acene isoelectronic structures, both compounds are stable because of the existence of more aromatic sextet rings, a dipolar character, and kinetic blocking. They exhibit unique packing in single crystals resulting from balanced dipole-dipole and [CH⋅⋅⋅π]/[CH⋅⋅⋅S] interactions.