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- Title
Dipolar Quinoidal Acene Analogues as Stable Isoelectronic Structures of Pentacene and Nonacene.
- Authors
Shi, Xueliang; Kueh, Weixiang; Zheng, Bin; Huang, Kuo‐Wei; Chi, Chunyan
- Abstract
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.New arrivals on the “cene”: Two dipolar quinoidal acene analogues were synthesized and they exhibit good solubility and high stability. They display distinctively different physical properties from the acene counterparts because of their closed‐shell quinoidal structure with a dipolar character in the ground state. Unique packing structures were observed in single‐crystal forms.
- Publication
Angewandte Chemie International Edition, 2015, Vol 54, Issue 48, p14412
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201507573