以环己烯为起始原料,首先经过两步改进的合成方法制备出2-乙氧羰基-3,4-四亚甲基吡咯,并用过量氢化铝锂将其高温还原得到2-甲基-3,4-四亚甲基吡咯,后者与被保护的4-甲醛基苯硼酸在三氟乙酸的催化作用下发生缩合反应,用2,3-二氯-5,6-二氰基-1,4-苯醌(DDQ)氧化并依次用三乙胺和三氟化硼-乙醚处理后,得到一种新型的中位取代苯硼酸的含稠合外环的硼-二吡咯亚甲基类(BDP)染料衍生物.通过紫外-可见吸收光谱及荧光光谱滴定方法,研究了该染料在特定pH值下对D-果糖、D-半乳糖、D-葡萄糖等3种单糖的响应能力,上述3种单糖与BDP染料衍生物的键合既表现在吸收光谱上,也表现在荧光发射光谱上,并且通过对荧光滴定数据的非线性拟合分析,BDP染料衍生物1与D-果糖、D-半乳糖、D-葡萄糖的结合常数分别为1045、445和130 L/mol.因此该染料衍生物作为单糖的荧光探针,具有灵敏度高、选择性较好等优点;另外,还初步探讨了该荧光探针的传感机理.
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