Quinoxaline-annelated Z-shaped quadruple-bridged orthocyclophanes: synthesis and crystal structures |
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Authors: | Teh-Chang Chou Kung-Ching Liao |
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Affiliation: | a Department of Applied Chemistry, Chaoyang University of Technology, Wufong, Taichung 41369, Taiwanb Department of Chemistry and Biochemistry, National Chung Cheng University, Minsyong, Chiayi 621, Taiwan |
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Abstract: | A three-step synthesis of nineteen Z-shaped quadruple-bridged [6,6] and [6,4]orthocyclophanes comprising two quinoxaline-based sidewalls are described. The synthesis began from the bis-Diels−Alder adducts B1-B3 followed by ruthenium-promoted oxidation of dichloroetheno-bridges in the adducts to generate a bis-α-diketones, which were then condensed with various arene-1,2-diamines (9a-g) to construct sidewalls (phane parts) of Z-shaped quadruple-bridged orthocyclophanes D1-3, D2g, and D3g. Single-crystal structures of six orthocyclophanes (D1a, D2a, D2f, D3f, D2g-α, and D3g-α) were obtained and revealed that the CAr−H?π and π?π stacking interactions between N-containing arene rings are the major driving force for molecular assembly and crystal packing, in addition to the interactions involving the polar OCH3 groups and the solvate molecules. |
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Keywords: | Cyclophanes Aza-arenes Arene-arene interaction Crystal structure |
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