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

Author(s): Rudebeck, EE; Ashton, TD; Henwood, AF; Gunnlaugsson, T; Pfeffer, FM;
Details: Publication Year 2023-07-11,Volume 21,Issue #29,Page 5970-5976
Journal Title: Organic & Biomolecular Chemistry
Abstract: 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.
Publisher: ACS
Research Division(s): Chemical Biology
PubMed ID: 37431835
Publisher's Version: https://doi.org/10.1039/d3ob00737e
Open Access at Publisher's Site: https://doi.org/10.1039/d3ob00737e
Terms of Use/Rights Notice: Refer to copyright notice on published article.

Creation Date: 2023-07-21 09:41:28

Last Modified: 2023-08-16 02:52:43