中位取代苯甲酸基的硼-二吡咯亚甲基染料衍生物的合成与性质

将2,4-二甲基-3-乙基吡咯与对-乙氧羰基苯甲醛在三氟乙酸的催化作用下发生缩合反应,用23,-二氯-5,6-二氰基-14,-苯醌(DDQ)氧化,并依次用N(Et)3和BF3.OEt2处理,得化合物(2),再将(2)在甲醇-氢氧化钠溶液中加热回流、水解,制备出中位取代苯甲酸基的硼-二吡咯亚甲基染料衍生物(1)。采用荧光光谱滴定方法研究了它的金属离子传感性能。结果表明,在甲醇溶液中,染料(1)显示出显著的对汞离子具有选择性的"开-关"型亲离子荧光团响应,可作为检测汞离子的荧光探针。另外,还初步探讨了荧光探针的检测机制。

Synthesis and properties of boron-dipyrromethene (BDP) derivative substituted with benzoyloxy subunit at meso-position

2,4-Dimethyl-3-ethylpyrrole was reacted with 4-ethoxycarbonyl benzaldehyde in the presence of CF3COOH as catalyst and oxidated with DDQ,followed by treatment with N(Et)3 and BF3·Et2O to provide compound(2).The title boron-dipyrromethene(BDP) derivative(1) substituted with benzoyloxy subunit at meso-position was obtained by the hydrolysis of(2) in basic methanol at reflux condition.Its metal ion sensing properties were investigated by fluorescent titrations of(1) with various metal cations.The results showed that in methanol,BDP derivative(1) exhibits pronounced on-off-type fluorescence response with high selectivity towards Hg2+ among the examined metal ions,which can make it possible to be used as fluorescent probe for detection of Hg2+.Moreover,its sensing mechanism is also discussed.