A new fluorescent sensor 1 for F − was designed and synthesized through the condensation of 1,8-anthracene diamine and indole-2-carboxylic acid via DCC. Upon mixing with F − in DMSO:CH 2 Cl 2 (1:9, v/v), the increases in fluorescence could be observed. No obvious changes could be found upon the addition of other anions such as Cl − , Br − , I − , NO 3 − , HSO 4 − , H 2 PO 4 − , AcO − . Job plots indicated the formation of 1:1 complex of 1 and F − with association constant K = 7.3 × 10 4 M −1 . 1 H NMR titration experiments indicated that fluoride anion had strong hydrogen bonding interactions not only with the N–H of the amide but also with the indole N–H and the 9-H of anthracene. This rigidified the structure and led to the reduction of the efficiency of the PET process and the enhancement of fluorescence intensity.
Sensors and Actuators B: Chemical – Elsevier
Published: Aug 18, 2009
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