Two-photon absorbing 8-hydroxy-benzo[g]coumarins with giant Stokes shifts: an environment-insensitive dye platform for probing biomolecules†,Journal of Materials Chemistry B

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Two-photon absorbing 8-hydroxy-benzo[g]coumarins with giant Stokes shifts: an environment-insensitive dye platform for probing biomolecules†
Journal of Materials Chemistry B ( IF 6.1 ) Pub Date : 2018-06-13 00:00:00 , DOI: 10.1039/c8tb01144c
Sourav Sarkar _{1,

2,

3,

4,

5} , Mithun Santra _{1,

2,

3,

4,

5} , Subhankar Singha _{1,

2,

3,

4,

5} , Yong Woong Jun _{1,

2,

3,

4,

5} , Ye Jin Reo _{1,

2,

3,

4,

5} , Hye Rim Kim _{1,

2,

3,

4,

5} , Kyo Han Ahn _{1,

2,

3,

4,

5}

Affiliation

Fluorescent compounds with distinct photophysical properties are essential for the development of optical probes for chemical, biological, and environmental species, in addition to optoelectronic devices. In this context, we synthesized a series of 3-substituted-8-hydroxybenzo[g]coumarin derivatives and characterized their photophysical and cellular imaging properties. Being dipolar π-extended coumarin analogues, they have intramolecular charge-transfer character and good two-photon imaging capability, as shown for two selected dyes. Most of the dyes emit in a wavelength range of 530–580 nm in aqueous media and show large Stokes shifts as high as 197 nm. In spite of its dipolar nature, the 3-pyridinium-substituted derivative 5h notably shows insignificant solvatochromism as well as viscosity- and polarity-insensitive emission intensity, offering an ideal dye platform for probing biological targets. As a demonstration, we prepared an esterase probe based on it, which shows ratiometric sensing behavior.

中文翻译：

具有巨大斯托克斯位移的双光子吸收8-羟基-苯并[ g ]香豆素：用于探测生物分子的对环境不敏感的染料平台†

除了光电装置外，具有独特光物理性质的荧光化合物对于开发化学，生物和环境物种的光学探针也是必不可少的。在这种情况下，我们合成了一系列的3-取代的8-羟基苯并[ g ]香豆素衍生物，并表征了它们的光物理和细胞成像特性。作为偶极π扩展的香豆素类似物，它们具有分子内电荷转移特性和良好的双光子成像能力，如两种选定的染料所示。大多数染料在水性介质中发射的波长范围为530–580 nm，并显示出高达197 nm的大斯托克斯位移。尽管具有偶极性质，但3吡啶取代的衍生物5h显着表现出微不足道的溶剂变色性以及对粘度和极性不敏感的发射强度，为探测生物靶标提供了理想的染料平台。作为演示，我们准备了一个基于它的酯酶探针，该探针显示了比例传感行为。

更新日期：2018-06-13

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