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首页> 外文期刊>Chemistry: A European journal >OFF-ON-OFF Red-Emitting Fluorescent Indicators for a Narrow pH Window
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OFF-ON-OFF Red-Emitting Fluorescent Indicators for a Narrow pH Window

机译：用于窄pH窗口的离上的红发荧光灯指示灯

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摘要

A unique combination of two independent mechanisms of fluorescence quenching, namely intramolecular charge transfer (ICT) from a peripheral donor and protonation of azomethine nitrogen atoms in zinc tetrapyrazinoporphyrazines (TPyzPz), provides a new possibility for sensing pH in a specific range. The pH selectivity was controlled by the different basicities of the donor for ICT (dimethylaminoaryl), which was connected to the macrocycle by π-extended linkers of different lengths. ICT and protonation have been studied in detail by photophysical, spectral (UV/Vis and MCD spectra), and electrochemical measurements, and further supported by theoretical calculations (DFT, TDDFT). The pH-sensing properties of the TPyzPzs have been investigated in THF and in water after anchoring the TPyzPzs to liposomes. The salient pK_a values were around 1.3 (azomethine nitrogen) and 2.29-4.76 (donor for ICT). The lead indicators (sensing over a pH range of 1.0-2.5) with fairly steep sensing profiles exhibited increases in fluorescence between the OFF/ON states of more than 20-fold and strong absorption in the red region (Q-band maximum >650 nm, ε≈2× 10~6m~(-1)cm~(-1)).
机译：来自锌四吡嗪卟啉（TPYZPZ）的外周供体的两个独立荧光猝灭机制，即分子内电荷（ICT）的两个独立机制，即氮杂甲硝基氮原子的质子化，提供了在特定范围内感测pH的新可能性。 pH选择性受到ICT（二甲基氨基芳基）的不同碱性的碱性，其通过不同长度的π-延伸的接头连接到大循环。通过光物理，光谱（UV / VIS和MCD光谱）和电化学测量和电化学测量有详细研究了ICT和质子化，并通过理论计算（DFT，TDDFT）进一步支持。在将TPYZPZ锚固到脂质体之后，在THF和水中研究了TPYZPZ的pH-感测性质。突出的PK_A值约为1.3（氮杂胺氮）和2.29-4.76（ICT供体）。具有相当陡峭的感测曲线的铅指示剂（在1.0-2.5的pH范围内）表现出在超过20倍的荧光之间的荧光增加，并且在红色区域中的强烈吸收（Q频带最大> 650nm ，ε≈2×10〜6m〜（-1）cm〜（-1））。

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  • 来源
    《Chemistry: A European journal》 |2017年第8期|共10页
  • 作者

    Antonin Cidlina; Miroslav Miletin; Mahtab Fathi-Rasekh; Victor N. Nemykin; Petr Zimcik; Veronika Novakova;

  • 作者单位

    Department of Pharmaceutical Chemistry and Pharmaceutical Analysis Faculty of Pharmacy in Hradec Kralove Charles University in Prague Heyrovskeho 1203 Hradec Kralove 500 05 (Czech Republic);

    Department of Pharmaceutical Chemistry and Pharmaceutical Analysis Faculty of Pharmacy in Hradec Kralove Charles University in Prague Heyrovskeho 1203 Hradec Kralove 500 05 (Czech Republic);

    Department of Chemistry and Biochemistry University of Minnesota Duluth 1039 University Drive Duluth MN 55812 (USA);

    Department of Chemistry and Biochemistry University of Minnesota Duluth 1039 University Drive Duluth MN 55812 (USA);

    Department of Pharmaceutical Chemistry and Pharmaceutical Analysis Faculty of Pharmacy in Hradec Kralove Charles University in Prague Heyrovskeho 1203 Hradec Kralove 500 05 (Czech Republic);

    Department of Biophysics and Physical Chemistry Faculty of Pharmacy in Hradec Kralove Charles University in Prague Heyrovskeho 1203 Hradec Kralove 500 05 (Czech Republic);

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 应用化学;
  • 关键词

    azomethine nitrogen; fluorescence; intramolecular charge transfer; phthalocyanines; sensors;

    机译：氮杂胺氮;荧光;分子内电荷转移;酞菁;传感器;

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