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首页> 外文期刊>European journal of organic chemistry >Systematic studies on photoluminescence of oligo(arylene-ethynylene)s: Tunability of excited states and derivatization as luminescent labeling probes for proteins
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Systematic studies on photoluminescence of oligo(arylene-ethynylene)s: Tunability of excited states and derivatization as luminescent labeling probes for proteins

机译：寡聚（亚芳基-亚乙炔基）的光致发光的系统研究：激发态的可调性和作为蛋白质发光标记探针的衍生化

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Functionalized oligo(phenylene-ethynylene)s (OPEs) with different conjugation lengths, p-X(C6H4C equivalent to C)(n)SiMe3 (n = 1-4; X = NH2, NMe2, H) were synthesized by Sonogashira coupling of (phenylene-ethynylene)s and 1-iodo-4-(trimethylsilylethynyl) benzene, followed by desilylation of the p-substituted (trimethylsilylethynyl) benzenes with potassium hydroxide. The photoluminescent properties for the OPE series with different chain lengths and their solvatochromic responses were examined. The absorption maxima were red-shifted with increasing numbers of -(C6H4C equivalent to C)- units (n), and a linear plot of the absorption energy maxima vs. 1 was obtained for each series. The emission spectra in dichloromethane showed a broad and structureless band, the energies of which (in wavenumbers) also fit linearly with 1. Both the absorption and emission wavelength maxima of the NH2- and NMe2-substituted OPEs exhibited significant solvent dependence, whereas the parent OPEs (X = H) showed only minor shifts of the values in different solvents. Substituent effects upon the photolumine scent characteristics of the OPEs and the tunability of the excited states were examined with the p-X(C6H4C equivalent to C)(n)SiMe3 (n = 2, 3; X = NH2, NMe2, H, SMe, OMe, OH, and F) series. The H- and F-substituted counterparts exhibited high-energy vibronically structured emissions attributed to the (3)(pi pi*) excited states of the (arylene-ethynylene) backbone. For compounds bearing NH2 and NMe2 groups, a broad red-shifted emission with a remarkable Stokes shift from the respective absorption maximum was observed, which can be assigned to an n -> pi* transition. The n - pi* assignment was supported by MO calculations on the model compounds P-X(C6H4C - C)(2)SiH3 (X = NH2, H). Functionalization of the oligo(arylene-ethynylene)s with the N-hydroxysuccinimidyl (NHS) moiety enabled covalent attachment of the fluorophore to HSA protein molecules. A series of fluorescent labels, namely p-X(C6H4C equivalent to C)(n)-C6H4NHS, (n = 1, X = NH2, NMe2, SMe, OMe, OH, F; n = 2, X = NH2, NMe2) and p-Me2NC6H4C-C(C4H2S)-C C equivalent to CC6H4NHS were synthesized, and their conjugates with HSA (human serum albumin) were characterized by MALDI-TOF mass spectrometry, UV/Vis absorption spectroscopy, and gel electrophoresis. (c) Wiley-VCH Verlag GmbH & Co.
机译：通过（苯撑）的Sonogashira偶联合成具有不同共轭长度的功能化低聚（亚苯基乙炔基）（OPE），pX（C6H4C相当于C）（n）SiMe3（n = 1-4; X = NH2，NMe2，H） -亚乙炔基）和1-碘-4-（三甲基甲硅烷基乙炔基）苯，然后用氢氧化钾将对位取代的（三甲基甲硅烷基乙炔基）苯甲硅烷基化。研究了不同链长的OPE系列的光致发光特性及其溶剂致变色反应。随着-（C6H4C等同于C）-单元（n）数量的增加，吸收最大值发生红移，并且每个系列均获得了吸收能量最大值与1 / n的线性关系图。二氯甲烷的发射光谱显示出较宽且无结构的谱带，其能量（波数）也与1 / n线性拟合。 NH 2和NMe 2取代的OPE的最大吸收和发射波长均表现出显着的溶剂依赖性，而母体OPE（X = H）在不同溶剂中仅显示出较小的偏移值。用pX（C6H4C相当于C）（n）SiMe3（n = 2，3; X = NH2，NMe2，H，SMe，OMe ，OH和F）系列。 H和F取代的对等物表现出归因于（亚芳基-亚乙炔基）骨架的（3）（pi pi *）激发态的高能纤维结构发射。对于带有NH2和NMe2基团的化合物，观察到较宽的红移发射，与相应的最大吸收值相比有明显的斯托克斯位移，这可以归因于n-> pi *跃迁。 MO模型化合物P-X（C6H4C-C）（2）SiH3（X = NH2，H）的MO计算支持n-pi *的分配。带有N-羟基琥珀酰亚胺基（NHS）部分的寡聚（亚芳基-亚乙炔基）功能化使荧光团与HSA蛋白分子共价连接。一系列荧光标记，即pX（C6H4C等同于C）（n）-C6H4NHS，（n = 1，X = NH2，NMe2，SMe，OMe，OH，F; n = 2，X = NH2，NMe2）和合成了相当于CC6H4NHS的p-Me2NC6H4C-C（C4H2S）-CC，并通过MALDI-TOF质谱，UV / Vis吸收光谱和凝胶电泳对它们与HSA（人血清白蛋白）的结合物进行了表征。 （c）Wiley-VCH Verlag GmbH＆Co.

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