Novel Fluorescent pH Sensors Based on Intramolecular Hydrogen Bonding Ability of Naphthalimide
Organic Letters2004Vol. 6(16), pp. 2757–2760
Citations Over TimeTop 13% of 2004 papers
Abstract
4-Piperidine-naphthalimide derivatives containing potential acceptors for hydrogen bonding were synthesized, and their fluorescence properties were examined. Some of the compounds with a 2-imino-oxalidin (thiazolidin) side chain at the imide moiety exhibit a strong fluorescence quench and some red shift in weakly acidic conditions, caused by the formation of an intramolecular hydrogen bond. Their pK(a) values were estimated to be about 6.4-7.5. The results showed that these compounds could serve as novel fluorescent pH sensors for further application. [structure: see text]
Related Papers
- → Iterative Multifunctionalization of Unactivated C−H Bonds in Piperidines by Way of Intramolecular Rh(II)-Catalyzed Aminations(2008)32 cited
- → Synthesis of a phosphine imide bearing a hydrosilane moiety, and its water-driven reduction to a phosphine(2013)13 cited
- → Intramolecular hydrogen bonding and intermolecular association of amino alcohols(1986)14 cited
- → Structure-activity relationship of cyclic imide herbicides. I. N-Substituted phenyl-3,4,5,6-tetrahydrophthalimides and related compounds.(1976)10 cited
- Design, synthesis and antitubercular evaluation of benzothiazinones containing a piperidine moiety(2018)