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首页> 外文期刊>Chemistry: A European journal >Boron Difluoride Curcuminoid Fluorophores with Enhanced Two-Photon Excited Fluorescence Emission and Versatile Living-Cell Imaging Properties
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Boron Difluoride Curcuminoid Fluorophores with Enhanced Two-Photon Excited Fluorescence Emission and Versatile Living-Cell Imaging Properties

机译：具有增强的双光子激发荧光发射和多功能活细胞成像特性的二氟化硼姜黄素荧光团

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摘要

The synthesis of boron difluoride complexes of a series of curcuminoid derivatives containing various donor end groups is described. Time-dependent (TD)-DFT calculations confirm the charge-transfer character of the second lowest-energy transition band and ascribe the lowest energy band to a cyanine-like transition. Photophysical studies reveal that tuning the donor strength of the end groups allows covering a broad spectral range, from the visible to the NIR region, of the UV-visible absorption and fluorescence spectra. Two-photon-excited fluorescence and Z-scan techniques prove that an increase in the donor strength or in the rigidity of the backbone results in a considerable increase in the two-photon cross section, reaching 5000GM, with predominant two-photon absorption from the S-0-S-2 charge-transfer transition. Direct comparisons with the hemicurcuminoid derivatives show that the two-photon active band for the curcuminoid derivatives has the same intramolecular charge-transfer character and therefore arises from a dipolar structure. Overall, this structure-relationship study allows the optimization of the two-photon brightness (i.e., 400-900GM) with one dye that emits in the NIR region of the spectrum. In addition, these dyes demonstrate high intracellular uptake efficiency in Cos7 cells with emission in the visible region, which is further improved by using porous silica nanoparticles as dye vehicles for the imaging of two mammalian carcinoma cells type based on NIR fluorescence emission.
机译：描述了一系列含有各种供体端基的类姜黄素衍生物的二氟化硼配合物的合成。与时间有关的（TD）-DFT计算可确定第二个最低能量跃迁带的电荷转移特性，并将最低能量带归为类似花菁的跃迁。光物理研究表明，调整端基的供体强度可以覆盖从可见光到NIR区域的紫外可见吸收光谱和荧光光谱。双光子激发荧光和Z扫描技术证明，供体强度或主链刚性的增加会导致双光子横截面显着增加，达到5000GM，并且主要从光子吸收两光子。 S-0-S-2电荷转移过渡。与半姜黄素衍生物的直接比较表明，姜黄素衍生物的双光子活性带具有相同的分子内电荷转移特性，因此是由偶极结构引起的。总体而言，这项结构关系研究可以使用一种在光谱NIR区域内发射的染料来优化双光子亮度（即400-900GM）。此外，这些染料在Cos7细胞中表现出较高的细胞内摄取效率，并且在可见光区域有发射，这可通过使用多孔二氧化硅纳米粒子作为染料媒介物，基于NIR荧光发射法对两种哺乳动物癌细胞类型成像来进一步提高。

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