The physical properties of biaryl-containing compounds are known to be highly dependent on molecular geometry. We have synthesized two 6H-benzo[c]chromen-6-one derivatives where a lactone �tether� between the two phenyl rings should force a planar geometry. These biphenyl lactones contain a methoxy electron donor and a nitro or cyano electron acceptor at the 4 and 4' positions to affect charge transfer through the ring system. By varying the pH, we are able to reversibly and rapidly open and close the �tether� and thus switch the molecule in and out of planarity. The results of this pH-driven dihedral angle switching can be analyzed by UV-Vis and fluorescence spectroscopy. Progress toward analagous terphenyl derivatives with the capability to switch via both pH and redox reactions will also be reported.

Biphenyl and terphenyl lactone pH-driven molecular switches

245th National Meeting (2013)

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