Industrial & Engineering Chemistry Research, Vol.44, No.4, 847-851, 2005
Fluorometric detection of pH and metal cations by 1,4,7,10-tetraazacyclododecane (Cyclen) bearing two anthrylmethyl groups
1,4,7,10-Tetraazacyclododecane (cyclen) bearing two anthrylmethyl groups (1,7-bis(9-anthryl-methyl)-1,4,7,10-tetraazacyclododecane, L2) was synthesized and used as a fluorescent chemosensor for detection of pH and transition metal cations in aqueous solution. The fluorescent response and complexation properties of L2 were studied in comparison with those of a cyclen with a single anthrylmethyl group that was previously reported (1-(9-anthrylmethyl)-1,4,7,10-tetraazacyclododecane, L1). Although L2 showed a less sharp response than L1, L2 demonstrated fluorescence behavior similar to that of L1, showing strong fluorescence at a low-pH region (pK(a) = 8.4) and in the presence of Zn2+ and Cd2+ but showing weak fluorescence at a high-pH region and in the presence of Cu2+. Chemical stability test by H-1 NMR revealed that L2 is very stable even if left to stand under a humid atmosphere for 30 days, suggesting that L2 may be a potential effective fluorescent chemosensor for detection of pH and transition metal cations in aqueous solution.