BODIPY-吡咯类荧光染料的合成及光谱识别性能

Synthesis and Spectroscopic Sensing Properties of BODIPY-Pyrrole-Based Fluorescent Dyes

采用Knoevenagel反应以氟化硼配位二吡咯甲川类荧光染料BODIPY(4,4-difluoro-4-bora-3a,4adiaza-s-indacene)为母体,经吡咯甲醛或杯吡咯甲醛合成了四个BODIPY荧光染料1a^1d,用MS,NMR和元素分析进行结构确证。考察了它们的紫外吸收光谱与荧光发射光谱,结果表明1a^1d具有较高的摩尔吸光系数,在BODIPY母环的3,5位双取代物(1c和1d)相对于单取代物(1a和1b)其最大吸收波长和发射波长分别红移了约90nm和80nm,说明BODIPY-吡咯衍生物中共轭程度增强,光谱出现红移。阴离子识别研究表明,1b和1d能够与Cl-形成多重氢键,导致吸收光谱红移和荧光猝灭。

Four novel BODIPY-based fluorescent dyes （1a -1d） incorporating pyrrole or calixpyrrole moieties were synthesized by Knoevenagel reaction and characterized by MS, NMR and elemental analysis. The investigation of UV-Vis absorption and fluorescent emission of as-synthesized compounds indicated that 1a - 1d exhibit high molar extinction coefficients. Furthermore, compared to mono-substituted 1a and 1b, di-substituted 1c and ld emerge about 90nm and 80nm red shift in absorption and emission spectra, respectively, which is caused by increasing the conjugation of BODIPY dyes. According to the investigation of anion recognition, 1b and 1d can bind Cl^- through multiple hydrogen bonds, which is responsible for the red shift in absorption and fluorescence quenching.