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以双碘代芳醛4-[N,N-二(4-碘苯基)氨基]苯甲醛与4-乙烯基吡啶通过钯催化双位点Heck偶联反应制备了中间体TPAPy,TPAPy再与碘代十八烷反应得到吡啶盐衍生物TPAPyS.目标化合物的结构经过红外光谱、核磁共振谱、高分辨质谱确认,测定了吡啶盐TPAPyS在固态、水溶液中及乙醇/水混合溶液中的荧光光谱.吡啶盐TPAPyS在固体状态下发出暗红色荧光,荧光发射峰为654 nm,测得固体量子产率为3.83%.TPAPyS在水溶液中发出红色荧光,荧光发射峰为647 nm.在乙醇/水混合溶液中,化合物TPAPyS的荧光发射峰位于612~640 nm.测定了吡啶盐TPAPyS与牛血清蛋白(BSA)、胱氨酸(DCys)及半胱氨酸(Cys)在生理条件下的光谱行为,吡啶盐TPAPyS与BSA、氨基酸作用后荧光发射强度均增加.吡啶盐TPAPyS是一种可溶于水的红光发射材料,荧光发射峰位于近红外波段,可作为荧光探针用于牛血清蛋白和氨基酸的检测.
The intermediate TPAPy was prepared by the palladium-catalyzed double-site Heck coupling reaction using 4- (N, N-bis (4-iodophenyl) amino] benzaldehyde with 4- Iodine octadecane to give the pyridine salt derivative TPAPyS.The structure of the target compound was confirmed by infrared spectroscopy, nuclear magnetic resonance spectrum and high resolution mass spectrometry, and the fluorescence spectra of pyridinium salt TPAPyS in solid, aqueous solution and ethanol / water mixed solution were determined. . The pyridine salt TPAPyS emits a dark red fluorescence under the solid state with a fluorescence emission peak of 654 nm and a solid quantum yield of 3.83% .TPAPyS emits red fluorescence in aqueous solution with a fluorescence emission peak of 647 nm. In the ethanol / water mixture The fluorescence emission peak of the compound TPAPyS was between 612 and 640 nm.The spectral properties of TPAPyS, bovine serum albumin (BSA), cystine (DCys) and cysteine (Cys) were measured under physiological conditions, Pyridine salt TPAPyS and BSA, fluorescence intensities after amino acid increase.Palladium salt TPAPyS is a water-soluble red light-emitting material, the fluorescence emission peak in the near-infrared band can be used as a fluorescent probe for bovine serum albumin and Amino acid detection.