四苯基乙烯双取代去氢枞酸的合成及性能研究

Synthesis and Properties of Tetraphenylethylene Disubstituted Dehydroabietic Acid

从歧化松香中提取去氢枞酸(DHA),经酰氯化后与4,4-二羟基四苯基乙烯(2OH-TPE)反应,合成了具有聚集诱导发光(AIE)性质的四苯基乙烯双取代去氢枞酸(2DHA-TPE),通过NMR和MS对2DHA-TPE的结构进行表征,研究了DHA的引入对TPE分子荧光性质的影响。结果表明,引入DHA后的2DHA-TPE分子仍具有AIE性质,其熔点和热分解温度分别为145℃和273℃;2DHA-TPE晶体荧光发射波长为464 nm,荧光量子产率为47.32%;2DHA-TPE无定形态荧光发射波长红移至485 nm,荧光量子产率降至21.78%;2DHA-TPE具有良好的热稳定性、力致荧光变色(MC)和结晶诱导荧光增强(CIEE)性质,在丙酮气氛下,其晶态与无定形态之间的荧光可实现相互转变。

Dehydroabietic acid(DHA)was extracted from disproportionated rosin,and then reacted with 4,4-dihydroxytetraphenylethylene(2OH-TPE)after acylation chlorination to synthesize tetraphenylethylene disubstituted dehydroabietic acid(2DHA-TPE)which possessed a property of aggregation-induced emission(AIE).Moreover,we confirmed the structure of 2DHA-TPE by NMR and MS,and studied the effect of the introduction of DHA on the fluorescence property of TPE.The results show that 2DHA-TPE with the introduction of DHA still possesses AIE property,and its melting point and thermal decomposition temperature are 145℃and 273℃,respectively.The fluorescence emission wavelength of 2DHA-TPE crystal is 464 nm,and the fluorescence quantum yield is 47.32%.The fluorescence emission wavelength of 2DHA-TPE amorphous form red-shifts to 485 nm,and the fluorescence quantum yield reduces to 21.78%.In acetone atmosphere,the fluorescence between crystalline state and amorphous form of 2DHA-TPE can realize mutual transformation,indicating 2DHA-TPE has good thermal stability,mechanofluorochromism(MC)and crystallization-induced emission enhancement(CIEE)properties.