College of Chemistry & Environmental Science, Hebei University, Baoding, 071002, China.
Department of Clinical Pharmacy, Affiliated Hospital of Hebei University, Baoding, 071002, China.
J Mater Chem B. 2023 Mar 22;11(12):2714-2726. doi: 10.1039/d2tb02639b.
In this paper, a series of polyamide derivatives (PAMs) containing morpholine groups were prepared by Ugi polymerization from dialdehyde, diacid, -(2-aminoethyl)-morpholine and isonitrile compounds as novel multi-responsive fluorescent sensors. As non-conjugated light-emitting polymers, PAMs were endowed with unique polymerization-induced emission (PIE) performance at 450 nm by through-space conjugation (TSC) between heteroatoms and heterocycles. It was also found that PAMs exhibited reversible responses to the external temperature and pH values and became responsive fluorescent switches. In addition, PAMs can specifically recognize Fe with a limit of detection (LOD) of 54 nM and the introduction of EDTA reversibly restores the fluorescence of the quenched PAMs-Fe system. By virtue of thermosensitivity, PAMs are easily separated from the above system by changing the temperature above or below the lower critical solution temperature (LCST). It is worth noting that PIE-active PAMs with good biocompatibility can selectively accumulate in lysosomes due to the presence of morpholine groups, and its Pearson colocalization coefficient is as higher as 0.91. Furthermore, a PIE-active PAM was successfully used to track exogenous Fe in lysosomes. In conclusion, these multi-functional PIE-active PAMs have higher potential applications in biomedical or environmental fields.
本文通过 Ugi 聚合反应，以二醛、二酸、(2-氨基乙基)吗啉和异腈化合物为原料，制备了一系列含吗啉基的聚酰胺衍生物(PAMs)，作为新型的多响应荧光传感器。作为非共轭发光聚合物，PAMs 通过杂原子和杂环之间的隔空共轭(TSC)赋予了独特的聚合诱导发光(PIE)性能，在 450nm 处发光。研究还发现，PAMs 对外界温度和 pH 值表现出可逆的响应，成为响应性荧光开关。此外，PAMs 可以特异性识别 Fe，检测限(LOD)为 54nM，EDTA 的引入可以可逆地恢复被猝灭的 PAMs-Fe 体系的荧光。由于具有温敏性，PAMs 可以通过改变温度高于或低于低临界溶液温度(LCST)，很容易从上述体系中分离出来。值得注意的是，由于含有吗啉基团，具有 PIE 活性的 PAMs 具有良好的生物相容性，能够选择性地在溶酶体中积累，其 Pearson 共定位系数高达 0.91。此外，成功地将 PIE 活性的 PAM 用于跟踪溶酶体中的外源性 Fe。综上所述，这些多功能 PIE 活性 PAMs 在生物医学或环境领域具有更高的潜在应用价值。
