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Dipolar Quinoidal Acene Analogues as Stable Isoelectronic Structures of Pentacene and Nonacene
Author(s) -
Shi Xueliang,
Kueh Weixiang,
Zheng Bin,
Huang KuoWei,
Chi Chunyan
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201507573
Subject(s) - acene , pentacene , chemistry , dipole , crystallography , character (mathematics) , computational chemistry , chemical physics , photochemistry , stereochemistry , molecule , organic chemistry , geometry , mathematics , layer (electronics) , thin film transistor
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.