Synthesis of Vinylnaphthofurans and NMR Analysis of their Photoswitching

An easy synthesis of photochromic vinylnaphthofurans by the acid‐catalyzed one‐pot reaction of naphthols with but‐2‐yne‐1,4‐diols is described. These uncolored polyaromatic compounds are activated by UV light, at room temperature, and converted through a stilbene‐type electrocyclization into a therm...

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Bibliographic Details
Published in:European journal of organic chemistry 2021-04, Vol.2021 (13), p.1979-1988
Main Authors: Graça, Vânia, Berthet, Jérôme, Sousa, Céu M., Delbaere, Stephanie, Coelho, Paulo J.
Format: Article
Language:English
Subjects:
Chemical Sciences
Diols
Electrocyclization
Naphthofurans
NMR
Nuclear magnetic resonance
One-pot synthesis
Photochromism
Room temperature
Stilbene
Thermal stability
Ultraviolet radiation
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Summary:An easy synthesis of photochromic vinylnaphthofurans by the acid‐catalyzed one‐pot reaction of naphthols with but‐2‐yne‐1,4‐diols is described. These uncolored polyaromatic compounds are activated by UV light, at room temperature, and converted through a stilbene‐type electrocyclization into a thermally stable orange species, which can be switched back using visible light. The behavior of these photoswitches was elucidated using NMR, which allowed to identify the photoisomers and some side‐products, formed after prolonged UV irradiation. An easy synthesis of photochromic vinylnaphthofurans by the acid‐catalyzed one‐pot reaction of naphthols with but‐2‐yne‐1,4‐diols is described. These polyaromatic compounds switch between uncolored (Vis) and colored (UV) states at room temperature. NMR analysis of irradiated solutions allowed to identify the photoisomers and some side‐products.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202100114