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Synthesis of 3,4-dihydroxy-1,8-naphthalimides with inbuilt catechol and crown ether functionalities.

Elley E RudebeckTrent D AshtonAdam F HenwoodThorfinnur GunnlaugssonFrederick M Pfeffer
Published in: Organic & biomolecular chemistry (2023)
Herein the synthesis of 1,8-naphthalimides functionalised as the 3,4-dihydroxy-1,8-naphthalimide (catechol, Nap-Cat) and the corresponding 15-crown-5 (Nap-Crown) is reported. These compounds represent the first examples where these two recognition groups are directly incorporated into the 1,8-naphthalimide ring system. Both Nap-Cat and Nap-Crown were evaluated for their capacity to respond to analytes such as H 2 O 2 (a mimic for cellular oxidation) and metal ions (as elements of environmental and physiological interest). While slow oxidation was observed for Nap-Cat upon prolonged exposure to H 2 O 2 , no significant changes in photophysical properties were observed upon treatment of Nap-Crown with metal ions.
Keyphrases
  • quantum dots
  • hydrogen peroxide
  • fluorescent probe
  • climate change
  • human health