1-(3,4-二羟基苯甲酰基)芘的合成及其对硼酸的双重光谱响应

Synthesis and dual spectral response of boric acid for 1-(3,4-dihydroxy benzoic acid) pyrene

以芘和3,4-二甲氧基苯甲酰氯为原料,经酰基化、脱甲基反应合成了1-(3,4-二羟基苯甲酰基)芘;采用荧光光谱法和紫外-可见吸收光谱法研究了硼酸与1-(3,4-二羟基苯甲酰基)芘的相互作用.结果表明:硼酸使1-(3,4-二羟基苯甲酰基)芘在波长366 nm的吸光度减小、吸收峰蓝移至344 nm,379和399 nm处的荧光增强,其吸光度(366 nm)减小的程度和荧光(379 nm)增强的程度与硼酸的浓度均具有良好的线性关系.对反应机理进行了初步探讨,认为溶液中硼酸以B(OH)4-形式与1-(3,4-二羟基苯甲酰基)芘分子中的邻位酚羟基结合形成1∶2络合物.

1-（3,4-dihydroxy benzoic acid） pyrene was synthesized from pyrene and 3,4-dimetho-xyphenyl chloride by acylation and demethylation reaction.The interaction between boric acid and 1-（3,4-dihydroxy benzoic acid） pyrene was investigated via fluorescence and UV-Vis absorption spectroscopy.The results showed that the absorbance at 366 nm of 1-（3,4-dihydroxy benzoic acid） pyrene was decreased and blue shifted to 344 nm and the fluorescence intensities at 379 nm and 399 nm were increased upon the addition of boric acid into 1-（3,4-dihydroxy benzoic acid） pyrene system.The absorbance reduce degree（366 nm） and fluorescence enhancement degree（379 nm） were well linearly related to the concentration of boric acid.Moreover,the reaction mechanism was preliminarily discussed,it was found that 1-（3,4-dihydroxy benzoic acid） pyrene formed a complex in 2：1 binding model through the o-hydroxy of phenolic with B（OH）-4 which was the form of boric acid existed in solution.