Dipolar Quinoidal Acene Analogues as Stable Isoelectronic Structures of Pentacene and Nonacene
KAUST DepartmentChemical Science Program
Homogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Online Publication Date2015-10-08
Print Publication Date2015-11-23
Permanent link to this recordhttp://hdl.handle.net/10754/623136
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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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