Dipolar Quinoidal Acene Analogues as Stable Isoelectronic Structures of Pentacene and Nonacene

Xueliang Shi, Weixiang Kueh, Bin Zheng, Kuo-Wei Huang, Chunyan Chi

Research output: Contribution to journalArticlepeer-review

24 Scopus citations

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 [C-H⋯π]/[C-H⋯S] interactions.
Original languageEnglish (US)
Pages (from-to)14412-14416
Number of pages5
JournalAngewandte Chemie International Edition
Volume54
Issue number48
DOIs
StatePublished - Oct 8 2015

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