College of Chemistry and Chemical Engineering, Neijiang Normal University, Neijiang, China.
Luminescence. 2024 Aug;39(8):e4868. doi: 10.1002/bio.4868.
A pair of 1,8-naphthalimides (NPIs) were designed and successfully synthesized through embellishing amino-containing NPI with 4-diethylaminosalicyladehyde and 4-diethylaminobenzaldehyde, respectively. Their structures were fully confirmed by H/C NMR, HR-MS and FT-IR spectroscopic studies. Their photophysical properties were systematically investigated in different solvents of varied polarity, in THF/water mixtures with varying water fractions (f), and in THF solvent with varying concentrations of NPIs. It inferred that the distinct differences in emission between two NPIs during self-assembled process could be ascribed that the hydroxyl-containing NPI allowed the excited-state intramolecular proton transfer process between -OH and CH=N units in the aggregation state. Interestingly, the solid of 4-diethylaminosalicyladehyde-functionalized NPI exhibited multi-stimuli-responsive fluorescence changes involving mechanofluorochromism and HCl/NH vapor stimulus-induced conversion. However, no remarkable change was observed in the photoluminescence (PL) spectra for the solid of 4-diethylaminobenzaldehyde-functionalized NPI under the stimuli of mechanical force and organic solvent.
一对 1,8-萘二甲酰亚胺（NPIs）通过分别用 4-二乙氨基水杨醛和 4-二乙氨基苯甲醛修饰含氨基的 NPI 成功设计并合成。通过 H/C NMR、HR-MS 和 FT-IR 光谱研究充分证实了它们的结构。在不同极性的不同溶剂、不同水分数（f）的 THF/水混合物以及不同浓度的 NPIs 的 THF 溶剂中系统地研究了它们的光物理性质。推断在自组装过程中，两种 NPI 之间发射的明显差异可以归因于含羟基的 NPI 允许在聚集态下-OH 和 CH=N 单位之间发生激发态分子内质子转移过程。有趣的是，4-二乙氨基水杨醛功能化 NPI 的固体表现出涉及机械变色和 HCl/NH 蒸气刺激诱导转换的多刺激响应荧光变化。然而，在机械力和有机溶剂的刺激下，4-二乙氨基苯甲醛功能化 NPI 的固体的光致发光（PL）光谱没有观察到明显的变化。
