Synthesis,Structural Characterization,and Reductive Cleavage of an Oxygen-Containing Naphthyl Macrocycle |
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| Authors: | Dr Zheng Zhou Matthew Pennachio Dr Zheng Wei Maxi L Heldner Prof?Dr Marina A Petrukhina Dr Tobias A Schaub |
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| Institution: | 1. Department of Chemistry, University at Albany State University of New York, 1400 Washington Avenue, Albany, NY 12222 USA;2. Institute of Organic Chemistry, Ruprecht-Karls-University Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany |
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| Abstract: | A small macrocycle comprising ether-bridged naphthyl units was prepared in a two-step synthesis. Single-crystal X-ray diffraction of two polymorphs are reported, one of which showed multiple C?H???πnaphthyl interactions of a solvent molecule in the cavity of the macrocycle. Chemical reduction led to C?O bond cleavages accompanied by a Z/E isomerization. The resulting twofold negatively charged (E)-1,2-bis(2-naphthyl)ethylene fragment was isolated as its potassium salts. Electronic characterization revealed a singlet ground state, and a marked distortion of the central ethylene unit was observed upon electron uptake. |
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| Keywords: | alkali metals chemical reduction DFT calculations macrocycle reductive C?O cleavage X-ray diffraction |
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