Noncommutative Switching of Double Spiropyrans

The Journal of Physical Chemistry. a
Luuk KortekaasWesley R Browne

Abstract

The spiropyran family of photochromes are key components in molecular-based responsive materials and devices, e.g., as multiphotochromes, covalently coupled dyads, triads, etc. This attention is in no small part due to the change in properties that accompany the switch between spiropyran and merocyanine forms. Although the spiropyran is a single structural isomer, the merocyanine form represents a family of isomers (TTT, TTC, CCT, etc.) and protonation states. Combining two spiropyrans into one compound increases the number of possible structures dramatically and the interaction between the units determines, which are impeded due to intramolecular quenching of excited states. Here, we show that the coupling of two spiropyran photochromes through their phenol units yields favorable interactions (crosstalk) between the components that provides access to species inaccessible with the component monospiropyran alone. Specifically, the ring opening of one spiropyran unit, which is thermally stable at -30 °C, prevents ring opening of the second spiropyran unit. Furthermore, whereas protonated E- and Z-monomerocyanines were previously shown to undergo thermal- and photo-equilibration, the corresponding protonated E- and Z- bimerocyanin...Continue Reading

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Methods Mentioned

BETA
nuclear magnetic resonance
NMR

Software Mentioned

Gaussian16

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