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Naphthalimide-based fluorescent photoinduced electron transfer sensors for saccharides

机译：基于萘二甲酰亚胺的荧光光致电子转移糖传感器

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摘要

The design and synthesis of two novel fluorescent sensors based on the photoinduced electron transfer (PET) mechanism for the detection of saccharides in aqueous medium is described. These sensors are based on the 4-amino-1,8-naphthalimide fluorophore, which absorbs and emits at similar to 400 nm and similar to 530 nm, respectively. By incorporating a phenylboronic acid receptor at the 4-position through a piperazine linker, high sensitivity was achieved for the sensing of saccharides. Both probes showed pHdependent fluorescence intensities, with pK(a) values of 4.8 (PET-S1) and 4.4 (PET-S2), respectively. After binding with sugars, up to 50-fold and 5-fold fluorescence enhancements for PET-S1 and PET-S2 were observed at pH 7.4, which allows them to be used under physiological conditions. The switch-on responses of both probes toward saccharides demonstrating the suppression of PET from the amino group to the fluorophore. The probes showed high sensitivity towards D-fructose and D-sorbitol. Probe PET-S1 was used to detect fructose in honey and beverages with good recovery.
机译：描述和设计了两种基于光致电子转移（PET）机制的新型荧光传感器，用于检测水性介质中的糖类。这些传感器基于4-氨基-1,8-萘二甲酰亚胺荧光团，其吸收和发射波长分别接近400 nm和530 nm。通过通过哌嗪连接子在4位上掺入苯基硼酸受体，可实现高灵敏度的糖类检测。两种探针均显示pH依赖性荧光强度，pK（a）值分别为4.8（PET-S1）和4.4（PET-S2）。与糖结合后，在pH 7.4下观察到PET-S1和PET-S2的荧光增强多达50倍和5倍，这使它们可以在生理条件下使用。两种探针对糖类的接通反应均显示出PET从氨基到荧光团的抑制作用。探针显示出对D-果糖和D-山梨糖醇的高敏感性。探针PET-S1用于检测蜂蜜和饮料中的果糖，回收率高。

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