Long Wavelength Azo Dye Monomers for Photomechanical Applications

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Dr. Jason. G Gillmore, Chemistry

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Azo dyes have long been incorporated into photomechanical systems with promise as wireless actuators (White, T.J.; Broer, D.J. Nat. Mater. 2015, 14, 1087-1098). Most azo dyes photoisomerize in the ultraviolet to blue-green region of the electromagnetic spectrum. However, these high energy wavelengths are prone to competitive absorption by other components of photomechanical devices, and are correlated to high levels of photodegradation of the material. These wavelengths also limit any biomedical applications, as they are incompatible with human tissue. Recently, Aprahamian and coworkers published a series of BF2-coordinated azo dyes which photoisomerize in the red-orange (Yang, Y.; Hughes, P.; Aprahamian, I. J. Am. Chem. Soc. 2012, 134, 15221-15224) to near-infrared (Yang, Y.; Hughes, P.; Aprahamian, I. J. Am. Chem. Soc. 2014, 136, 13190-13193) region of the spectrum. At these wavelengths, competitive absorption and photodegradation are minimal, as is absorption by mammalian tissue. In the Gillmore organic photochemistry research group, we are preparing analogs of Aprahamian’s dyes with polymerizable “handles” which may be incorporated into photomechanical polymers. These polymers will be prepared and studied in collaboration with the materials science / mechanical engineering research group of Professor Matt Smith in the Hope College Engineering Department. Synthetic efforts to date and future plans for this nascent research collaboration are described in this poster.


This work has been supported by The Camille & Henry Dreyfus Foundation (Dreyfus Teacher-Scholar Award), the Michigan Space Grant Consortium (undergraduate fellowship program and faculty seed grant), and the Hope College Chemistry Department (Undergraduate Research Fund and Schaap Research Fellows program).

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