Turn-On Mode Fluorescence Switch by Using Negative Photochromic Imidazole Dimer,Journal of the American Chemical Society

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Turn-On Mode Fluorescence Switch by Using Negative Photochromic Imidazole Dimer
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2019-03-19 , DOI: 10.1021/jacs.9b01870
Katsuya Mutoh ₁ , Nanae Miyashita ₁ , Kaho Arai ₁ , Jiro Abe ₁

Affiliation

The development of fluorescence switchable molecules in several polar and apolar environments has been required for fluorescence imaging of nanostructures. Photochromic molecules are an important class for the reversible light-triggered fluorescence switching. Although many studies of fluorescence switching by using photochromic reactions have been reported, the report of photochromic molecules reversibly showing turn-on mode fluorescence switching has been limited in spite of their importance. Herein, we report the photoactivatable fluorescence based on negative photochromism, where the absorption spectrum of the compound after irradiation is blue-shifted relative to that before irradiation. We introduced naphthalimide units as a green fluorophore to the negative photochromic binaphthyl-bridged imidazole dimer. The fluorescence of the naphthalimide unit is efficiently quenched in the initial colored isomer (fluorescence quantum yield: Φfluo. = 0.01) by Förster resonance energy transfer. In contrast, the fluorescence quantum yield increases up to 0.75 in the transient isomer formed by the negative photochromic reaction. The fluorescence intensity thermally decreases with the thermal back reaction to form the original stable colored form. These results indicate that the negative photochromic molecules are suitable for turn-on mode fluorescence switches and will give an attractive insight for the development of reversible fluorescence switching molecules.

中文翻译：

使用负光致变色咪唑二聚体的开启模式荧光开关

纳米结构的荧光成像需要在几种极性和非极性环境中开发荧光可切换分子。光致变色分子是可逆光触发荧光转换的重要类别。尽管已经报道了许多使用光致变色反应进行荧光切换的研究，但关于光致变色分子可逆地显示开启模式荧光切换的报道尽管很重要，但仍受到限制。在此，我们报告了基于负光致变色的光活化荧光，其中化合物在辐照后的吸收光谱相对于辐照前发生蓝移。我们将萘二甲酰亚胺单元作为绿色荧光团引入负光致变色联萘桥联咪唑二聚体。通过 Förster 共振能量转移，萘二甲酰亚胺单元的荧光在初始有色异构体（荧光量子产率：Φfluo. = 0.01）中被有效淬灭。相比之下，负光致变色反应形成的瞬态异构体的荧光量子产率增加到 0.75。荧光强度随着热逆反应而热降低以形成原始稳定的有色形式。这些结果表明负光致变色分子适用于开启模式荧光开关，并将为可逆荧光开关分子的发展提供有吸引力的见解。75在由负光致变色反应形成的瞬态异构体中。荧光强度随着热逆反应而热降低以形成原始稳定的有色形式。这些结果表明负光致变色分子适用于开启模式荧光开关，并将为可逆荧光开关分子的发展提供有吸引力的见解。75在由负光致变色反应形成的瞬态异构体中。荧光强度随着热逆反应而热降低以形成原始稳定的有色形式。这些结果表明负光致变色分子适用于开启模式荧光开关，并将为可逆荧光开关分子的发展提供有吸引力的见解。

更新日期：2019-03-19

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