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Click chemistry to fluorescent hyperbranched polymeric sensors. 2. Synthesis, spectroscopic and cation-sensing properties of new green fluorescent 1,8-naphthalimides

机译:单击化学以荧光超支化聚合物传感器。 2.新型绿色荧光1,8-萘二甲酰亚胺的合成,光谱和阳离子传感性能

摘要

A new yellow-green emitting hyperbranched fluorescent sensor derived from 4-(N,N-dimethylaminoethylamine)-1,8-naphthalimide has been synthesized for the first time through click chemistry, and its properties have been compared to those of its low molecular weight reference compound. The reactive chromophore, bearing a triple bond, has been synthesized in high yield in a two-step procedure by microwave irradiation. Solvatochromic study of the hyperbranched probe in several solvents using E30, π∗ and SPP scales demonstrates that there is not a loss of sensitivity towards polarity when the sensor moiety is included in the hyperbranched structure. The ability of the new compounds to detect cations was evaluated in solution by the increase in their fluorescence intensity in the presence of metal ions (Cu, Zn, Ni, Co, Cd, Fe, Ag and Hg) and protons. The hyperbranched sensor demonstrated the same sensitivity towards metal cations and protons than the reference chromophore, working through a photoinduced electron transfer mechanism typical of a >fluorophore-spacer-receptor> system. Experiments of long-term immersion of acrylic films doped with the probes showed no extraction of the hyperbranched fluorescent sensor, whereas the low molecular weight compound was continuously extracted from the film.
机译:首次通过点击化学合成了一种由4-(N,N-二甲基氨基乙胺)-1,8-萘二甲酰亚胺衍生的新的黄绿色发射超支化荧光传感器,并将其性能与低分子量传感器进行了比较。参考化合物。带有三键的反应性发色团通过微波辐射以两步法高产率合成。使用E30,π*和SPP标度在几种溶剂中对超支化探针进行的溶剂变色研究表明,当传感器部分包含在超支化结构中时,对极性的敏感性不会降低。通过在金属离子(铜,锌,镍,钴,镉,铁,银和汞)和质子存在下增加荧光强度来评估溶液中新化合物检测阳离子的能力。超支化传感器对金属阳离子和质子的敏感性与参比发色团相同,这是通过>荧光团-间隔物-受体>系统典型的光致电子转移机理实现的。掺杂有探针的丙烯酸薄膜的长期浸泡实验表明,没有萃取出超支化荧光传感器,而低分子量化合物却是从薄膜中连续萃取出来的。

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