Abstract
Fluorinated indolylfulgides are a promising class of photochromic organic compounds for optical memory and switches. Absorption spectra, quantum yields, thermal stabilities, and photochemical fatigue resistances have been measured for a series of fluorinated indolylfulgides. The cyclizable form of the heptafluoropropyl-substituted 1,2-dimethylindolylfulgide displays the longest absorbance maxima yet reported for the cyclizable form of a fulgide. Photochemical durability was quantified in both solvent and polymer for the first time, with the trifluoromethyl derivative undergoing more than 2500 photochemical cycles before degrading by 20% in either environment. In addition, the thermal stability of the cyclizable form has been examined for the first time. Although each fulgide showed outstanding resistance to thermal stress in the C-form, the cyclizable form degraded rapidly at 80°C. These studies highlight the many advantageous properties associated with fluorination and identify areas for future improvements.
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