Dipolar Quinoidal Acene Analogues as Stable Isoelectronic Structures of Pentacene and Nonacene
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AbstractQuinoidal 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 [C-H⋯π]/[C-H⋯S] interactions.
CitationShi X, Kueh W, Zheng B, Huang K-W, Chi C (2015) Dipolar Quinoidal Acene Analogues as Stable Isoelectronic Structures of Pentacene and Nonacene. Angewandte Chemie International Edition 54: 14412–14416. Available: http://dx.doi.org/10.1002/anie.201507573.
SponsorsC.C. acknowledges financial support from the MOE Tier 1 grant (R-143-000-573-112), Tier 2 grant (MOE2014-T2-1-080), and Tier 3 programme (MOE2014-T3-1-004). K.-W.H. acknowledges financial support from KAUST. We thank Dr. Bruno Donnadieu and Dr. Tan Geok Kheng for the crystallographic analysis.
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