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Photo-driven near-IR fluorescence switch: synthesis and spectroscopic investigation of squarine-spiropyran dyad

机译：照片驱动的接近IR荧光开关：Squarine-Spiropyran Dyad的合成和光谱调查

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摘要

With the objective of developing near-infrared fluorescence switch molecules for potential applications, synthesis of new dyad with two methyl 3-(3',3'-dimethyl-6-nitrospiro[chromene-2,2'-indolin]-1'-yl) propanoate (6), spiropyran (SP), units as the photochromic acceptors and a near-infrared fluorescence probe, (E)-4-((1-(2-hydroxyethyl)-3,3-dimethyl-3H-indol-1-ium-2-yl)methylene)-2-((E)-(1-(2-hydroxyethyl)-3,3-dimethylindolin- 2-ylidene) methyl)-3-oxocyclobut-1-en-1-olate (SQ), (3) as fluorescent donor are described. Two SP units are attached to the two indole nitrogen of squarine core with almost no conjugation with the SQ unit. The spectroscopic properties of the newly synthesized dyad, SP-SQ-SP(7), and corresponding model compounds (SP, SQ) have been studied in acetonitrile solution, poly(ethylene glycol) (PEG) polymer matrices and in nanoparticle form dispersed in aqueous medium. These dyes (3 and 7) exhibited absorption in the range 550-670 nm, with significant absorption coefficients (10(-5) M-1 cm(-1)) in the ACN. The fluorescence emission spectra of these dyes cover very broad range from 630 to 750 nm and fluorescence quantum yields are of the order of 0.2 in ACN solution. External stimulations (ultraviolet light and visible light) generate reversible changes in the structure of 7, resulting in changes in the absorption spectra due to the presence of the two spiropyran units. The absorption spectrum of the MC, a ring open form of SP, in dyad SP-SQ-SP(7) has large spectral overlap with the fluorescence spectrum of the SQ unit. Thus, the fluorescence intensity of dyad 7 is modulated by reversible conversion among the two states of the photochromic spiropyran units and the fluorescence resonance energy transfer (FRET) between the MC form and the SQ unit. High-contrast "on/off" fluorescence switching is successfully achieved with remarkably fatigue resistance in solution, in polymer film and in nanoparticle form of dyad (7). The described results indicate that this system may represent an efficient fluorescent switch molecule in potentially rewritable high-density optical data or image storage utilizing near-infrared luminescence intensity readout schemes.
机译：凭借开发近红外荧光开关分子的潜在应用，用两个甲基3-（3'，3'-二甲基-6-氮杂物[Chrome烯-2,2'-Indolin] -1'-丙烷（6），螺吡喃（SP），单位作为光致变色受体和近红外荧光探针，（e）-4 - （（1-（2-羟基乙基）-3,3-二甲基-3h-indol -1-Ium-2-yl）亚甲基）-2 - （（e） - （1-（2-羟乙基）-3,3-二甲基吲哚啉-2- ylidene）甲基）-3-氧杂环-1-en-1 - 单纯（Sq），（3）描述为荧光供体。两个SP单元连接到Squarine芯的两个吲哚氮，几乎没有与SQ单元的缀合。已经在乙腈溶液中研究了新合成的Dyad，SP-SQ-SP（7）和相应的模型化合物（SP，SQ）的光谱性质，聚（乙二醇）（PEG）聚合物基质和分散在纳米粒子形状中水性介质。这些染料（3和7）在ACN中表现出550-670nm的吸收，具有显着的吸收系数（10（-5）m-1cm（-1））。这些染料的荧光发射光谱覆盖的覆盖范围为630至750nm，荧光量子产率为ACN溶液中的0.2级。外部刺激（紫外线和可见光）在7的结构中产生可逆变化，导致由于两个螺吡喃单元的存在，吸收光谱的变化。 MC，SP的环形开放形式的MC的吸收光谱具有大的光谱重叠，具有SQ单元的荧光光谱。因此，通过在光致变色螺吡喃单元的两个状态和MC形式和SQ单元之间的荧光共振能量转移（FRET）之间的可逆转换来调节DYAD 7的荧光强度。成功地实现了高对比度“ON / OFF”荧光切换，在溶液中具有显着的疲劳性，聚合物膜和纳米粒子形式的二元（7）。所描述的结果表明，该系统可以代表潜在可重写的高密度光学数据或利用近红外发光强度读数方案的图像存储的有效荧光开关分子。

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  • 来源
    《RSC Advances》 |2015年第118期|共9页
  • 作者

    Doddi Siva; Ramakrishna Bheerappagari; Venkatesh Yeduru; Bangal Prakriti Ranjan;

  • 作者单位

    Indian Inst Chem Technol CSIR Inorgan &

    Phys Chem Div Hyderabad 500607 Andhra Pradesh India;

    Indian Inst Chem Technol CSIR Inorgan &

    Phys Chem Div Hyderabad 500607 Andhra Pradesh India;

    Indian Inst Chem Technol CSIR Inorgan &

    Phys Chem Div Hyderabad 500607 Andhra Pradesh India;

    Indian Inst Chem Technol CSIR Inorgan &

    Phys Chem Div Hyderabad 500607 Andhra Pradesh India;

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  • 正文语种 eng
  • 中图分类 化学;
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