Enhancing the Potential of Fused Heterocycle‐Based Triarylhydrazone Photoswitches

L Hegedüsová, N Blaise, LF Pašteka… - … A European Journal, 2024 - Wiley Online Library
L Hegedüsová, N Blaise, LF Pašteka, Š Budzák, M Medveď, J Filo, B Mravec, C Slavov
Chemistry–A European Journal, 2024Wiley Online Library
Triarylhydrazones represent an attractive class of photochromic compounds offering many
interesting features including high molar absorptivity, good addressability, and extraordinary
thermal stability. In addition, unlike most other hydrazone‐based photoswitches, they
effectively absorb light above 365 nm. However, previously prepared triaryhydrazones suffer
from low quantum yields of the Z→ E photoisomerization. Here, we have designed a new
subclass of naphthoyl‐benzothiazole hydrazones that balance the most beneficial features …
Abstract
Triarylhydrazones represent an attractive class of photochromic compounds offering many interesting features including high molar absorptivity, good addressability, and extraordinary thermal stability. In addition, unlike most other hydrazone‐based photoswitches, they effectively absorb light above 365 nm. However, previously prepared triaryhydrazones suffer from low quantum yields of the ZE photoisomerization. Here, we have designed a new subclass of naphthoyl‐benzothiazole hydrazones that balance the most beneficial features of previously reported naphthoyl‐quinoline and benzoyl‐pyridine triarylhydrazones. These preserve the attractive absorption characteristics, exhibit higher thermal stability of the metastable form than the former and enhance the rate of the ZE photoisomerization compared to the later, as a result of the weakening of the intramolecular hydrogen bonding between the hydrazone hydrogen and the benzothiazole moiety. Introducing the benzothiazole motif extends the tunability of the photochromic behaviour of hydrazone‐based switches.
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