Synthesis, optical and electrochemical properties of new receptors and sensors containing anthraquinone and benzimidazole units

Novel anion receptors and sensors, HBIMANQ and BIMANQ fabricated from the imidazolole unit and anthraquinone moieties were synthesized. H-1 NMR spectroscopy and UV-vis titrations in DMSO-d(6) and DMSO, respectively, showed that both receptors underwent deprotonation at the NH- moiety of the amide-anthraquinone unit in the presence of basic anions such as F- and AcO-. These phenomena gave a dramatic color change due to charge transfer transition corresponding to the shift of lambda(max) from 371 nm to 489 nm. Redox chemistry of HBIMANQ and BIMANQ in the presence of anions (F-, Cl-, AcO-, BzO(-), and H2PO4-) using cyclic voltammetry showed the different CV responses upon addition of various anions. In the case of HBIMANQ with various anions, the CV changes are dependent on the basic strength of anions in order of F-> AcO-, BzO(-)> H2PO4-> Cl-, Br-. Interestingly, the CV responses of BIMANQ with H2PO4- exhibited the most significant changes. BIMANQ, thus, has an excellent electrochemical selectivity toward H2PO4-. (c) 2008 Elsevier Ltd. All rights reserved.