Pi-Expanded Coumarins with Switchable Propeller Geometries
Hintz, Heather A.
Sortedahl, Nicholas J.
Dahl, Bart J.
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The focus of this project is analyzing planar conjugated molecules as molecular geometric switches. Our mission is to synthesize and study different classes of pi-expanded oligocoumarins with Crankshaft and Propeller architectures. The aryl-aryl torsional angle of the oligopheny subunits is controlled by lactone bridging groups to force planar conjugation. The lactone bridges could be reversibly cleaved and re-formed by changes in pH to form an open and closed conformation. Planar compounds with extended pi-conjugation suffer from poor solubility due to strong pi-stacking interactions. The synthesis with various solubilizing groups and switching studies of these compounds could lead to applications in areas such as organic electronics, molecular machines, light-harvesting materials, drug administration and sensors.
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