Pyridyl-Endcapped Polyynes: Stabilized Wire-like Molecules

A 4‐ethynylpyridyl derivative with sterically shielding phenyl groups in the 3‐ and 5‐positions has been synthesized and used to terminate a series of polyynes. This approach allows for the synthesis of stable polyynes up to an octayne, twice as long as previous accessible for “unstabilized” pyridyl...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2016-11, Vol.55 (47), p.14802-14806
Main Authors: Krempe, Maximilian, Lippert, Rainer, Hampel, Frank, Ivanović-Burmazović, Ivana, Jux, Norbert, Tykwinski, Rik R.
Format: Article
Language:English
Subjects:
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electrochemistry
ethynyl pyridines
Metals
molecular wires
polyynes
porphyrins
Ruthenium
Shielding
Wire
Zinc
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Summary:A 4‐ethynylpyridyl derivative with sterically shielding phenyl groups in the 3‐ and 5‐positions has been synthesized and used to terminate a series of polyynes. This approach allows for the synthesis of stable polyynes up to an octayne, twice as long as previous accessible for “unstabilized” pyridyl‐endcapped polyynes. The potential of these polyynes as wire‐like linkers to metal centers is demonstrated by axial coordination of pyridyl groups to zinc‐ and ruthenium‐metalloporphyrins. Protective phenyl groups: A synthetic route to the longest known pyridyl‐endcapped polyynes is developed. The wire‐like molecules are stabilized through steric shielding from pyridyl substituents, and the polyynes serve as molecular wires through endcapping with either Zn‐ or Ru‐porphyrins via axial coordination.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201608633