Insights into the complexation of N-Allyl-4-(4-(N-phenylureido)benzylamino)-1,8-naphthalimide with various anions.

ABSTRACT: A new urea functionalised 4-amino-1,8-naphthalimide based fluorescent anion sensor was synthesised in 64% yield over three steps. Fluorescence and ¹H NMR titrations showed that the sensor complexes strongly with acetate and dihydrogen phosphate and to a lesser extent bromide. The corresponding binding stoichiometries were examined using ¹H NMR titrations. Results show that the sensor molecule initially forms 1:1 complexes through hydrogen bonding to the urea moiety, followed by secondary complexation to form higher order host:guest stoichiometries. Specifically, oxyanions complex to the sensor via hydrogen bonding through synergistic aryl C-H and N-H anion interactions in a 1:2 sensor:oxyanion arrangement. Furthermore, 2:1 sensor:oxyanion complexes are formed through

SUBMITTER: Blok AJ 

PROVIDER: S-EPMC5451411 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature