Visible-light circular dichroism of colourless chiral organic compounds enabled by interfacial charge-transfer transitions†,Chemical Communications

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Visible-light circular dichroism of colourless chiral organic compounds enabled by interfacial charge-transfer transitions†
Chemical Communications ( IF 4.3 ) Pub Date : 2018-07-06 00:00:00 , DOI: 10.1039/c8cc04916e
Jun-ichi Fujisawa _{1,

2,

3,

4} , Naohito Kaneko _{1,

2,

3,

4} , Takumi Eda _{1,

2,

3,

4} , Minoru Hanaya _{1,

2,

3,

4}

Affiliation

We report the visible-light circular dichroism (CD) of colourless organic compounds based on interfacial charge-transfer (ICT) transitions with TiO₂ nanoparticles. We employed three kinds of colourless chiral compounds, L-ascorbic acid, D-ascorbic acid, and L-noradrenaline. These compounds showed a broad ICT band in the visible region between 400 and 600 nm upon their chemisorption on TiO₂ nanoparticles. L-Ascorbic acid and L-noradrenaline adsorbed on the TiO₂ nanoparticles showed positive and negative CD signals in the visible region, respectively. D-Ascorbic acid, which is the enantiomer of L-ascorbic acid, exhibited positive CD signals in the visible region, but different g factors (Δε/ε) from those of TiO₂–L-ascorbic acid, well reflecting the different chirality of the substituent group. The visible-light CD based on ICT transitions enables selective visible-light CD sensing and imaging of colourless chiral biomolecules even if coexisting with other colourless chiral compounds such as proteins and DNA. Furthermore, the molecular dependence of the g factor allows us to identify chiral molecules.

中文翻译：

界面电荷转移跃迁可实现无色手性有机化合物的可见光圆二色性†

我们报告了基于TiO ₂纳米粒子的界面电荷转移（ICT）跃迁的无色有机化合物的可见光圆二色性（CD）。我们使用了三种无色手性化合物，L-抗坏血酸，D-抗坏血酸和L-去甲肾上腺素。这些化合物在TiO ₂纳米粒子上化学吸附后，在400至600 nm的可见光区显示出宽的ICT带。吸附在TiO ₂纳米颗粒上的L-抗坏血酸和L-去甲肾上腺素分别在可见光区域显示正CD信号和负CD信号。D-抗坏血酸，是L-抗坏血酸在可见光区域显示正CD信号，但与TiO ₂ -L-抗坏血酸的g因子（Δε / ε）不同，很好地反映了取代基的手性。即使与其他无色手性化合物（例如蛋白质和DNA）共存，基于ICT转换的可见光CD仍可以对无色手性生物分子进行选择性可见光CD感测和成像。此外，g因子的分子依赖性使我们能够鉴定手性分子。

更新日期：2018-07-06

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