Enhancing the Potential of Fused Heterocycle-Based Triarylhydrazone Photoswitches
Status PubMed-not-MEDLINE Language English Country Germany Media print-electronic
Document type Journal Article
Grant support
APVV-20-0098
Slovak Research and Development Agency
WA 1850/4-3
Deutsche Forschungsgemeinschaft
ITMS2014+: 313021X329
European Regional Development Fund
ITMS 26230120002
European Regional Development Fund
ITMS 2621012000
European Regional Development Fund
VI.C.212.016
Dutch Research Council (NWO)
- Keywords
- TD-DFT, hydrazones, photoswitches, thermal stability, transient absorption,
- Publication type
- Journal Article MeSH
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 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 Z→E 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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