A mechanophore is a stress-sensitive material that undergoes selective bond breakage caused by physical stress. In many cases, this selective bond breakage causes changes in the colorimetric and/or fluorescent properties of molecules. Colorimetric mechanophores that are highly sensitive to mechanical stress could be useful for monitoring the relative stability of infrastructure and for testing the stress tolerance of materials. This research explores the potential of mechanophores formed from the spyrolactone xanthene dyes rhodamine and fluorescein. These dyes can change from a closed, colorless form to an open, colored, fluorescent form. These xanthene compounds offer much promise because they have a high quantum yield, are easy monitoring of bond breakage through changes in color and fluorescence, and have known facile derivatization routes. Described herein, is the development of new fluorescent monomers using rhodamine and fluorescein and the testing of the materials formed for their ability to function as mechanophore polymers.

Formation and testing of xanthene-based mechanophores

245th National Meeting (2013)

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