Colourful 3-amino-1,8-naphthalimide alkyl-substituted fluorescent derivatives

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments Pub Date : 2024-08-30 DOI:10.1016/j.dyepig.2024.112424

Alex D. Johnson , Konrad Szaciłowski , David C. Magri

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Abstract

The optical properties of four 3-amino-1,8-naphthalimide derivatives differing in the degree of substitution at the amino functionality were synthesised and studied by UV–visible absorbance and fluorescence spectroscopy in 1:1 (v/v) methanol/water and methanol. The compounds were structurally characterized by NMR, IR and HRMS. The charge transfer absorbance band was observed to shift to longer wavelength with increasing ethyl substitution. The emission band was also observed to shift to longer wavelengths with a decrease in the emission intensity with increasing ethyl substitution due to the peri effect. Irradiation of dye methanol solutions and in the solid state with a 365 nm UV lamp reveals distinct emission colours for each compound. Significantly larger Stokes shifts are observed in methanol than in mixed aqueous methanol. Quantum chemical calculations at the B3LYP/TZVP level of theory provided insight into the optimized ground state geometry, frontier molecular orbitals levels and solute-solvent dynamics revealing a stronger hydrogen bond between the 3-amino-1,8-naphthalimides and methanol in the lowest S1 excited state. The dyes were tested as fluorescent stains in MCF-7 cancer cells and observed to emit green emission in various organelles.

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彩色 3-氨基-1,8-萘二甲酰亚胺烷基取代荧光衍生物

我们合成了四种 3-氨基-1,8-萘二甲酰亚胺衍生物，它们的光学性质因氨基官能团的取代程度不同而不同，并在 1:1 (v/v) 甲醇/水和甲醇中通过紫外可见吸光度和荧光光谱进行了研究。通过核磁共振、红外光谱和 HRMS 对化合物进行了结构表征。观察到电荷转移吸光带随着乙基取代度的增加而向长波长移动。此外，还观察到发射带随着乙基取代度的增加而向更长的波长移动，同时由于周效应，发射强度降低。用 365 nm 的紫外灯照射染料甲醇溶液和固态时，会发现每种化合物都有不同的发射颜色。在甲醇中观察到的斯托克斯偏移明显大于在混合甲醇水溶液中观察到的斯托克斯偏移。在 B3LYP/TZVP 理论水平上进行的量子化学计算深入了解了优化基态几何、前沿分子轨道水平和溶质-溶剂动力学，发现在最低 S1 激发态中，3-氨基-1,8-萘二甲酰亚胺与甲醇之间的氢键更强。这些染料作为荧光染色剂在 MCF-7 癌细胞中进行了测试，观察到它们在各种细胞器中发出绿色荧光。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Dyes and Pigments 工程技术-材料科学：纺织

CiteScore

8.20

自引率

13.30%

发文量

933

审稿时长

33 days

期刊介绍： Dyes and Pigments covers the scientific and technical aspects of the chemistry and physics of dyes, pigments and their intermediates. Emphasis is placed on the properties of the colouring matters themselves rather than on their applications or the system in which they may be applied. Thus the journal accepts research and review papers on the synthesis of dyes, pigments and intermediates, their physical or chemical properties, e.g. spectroscopic, surface, solution or solid state characteristics, the physical aspects of their preparation, e.g. precipitation, nucleation and growth, crystal formation, liquid crystalline characteristics, their photochemical, ecological or biological properties and the relationship between colour and chemical constitution. However, papers are considered which deal with the more fundamental aspects of colourant application and of the interactions of colourants with substrates or media. The journal will interest a wide variety of workers in a range of disciplines whose work involves dyes, pigments and their intermediates, and provides a platform for investigators with common interests but diverse fields of activity such as cosmetics, reprographics, dye and pigment synthesis, medical research, polymers, etc.