This study focuses on the synthesis and characterization of three azonaphtharylmide dyes, APAS, APASD, and APASTR, using naphthol AS, ASD, and ASTR couplers. The research also observes the presence of a hydrazone tautomer in a DMSO solution. It was characterized through spectroscopic analysis, which revealed three characteristic carbonyl carbon peaks in the C NMR spectrum. The calculated low LUMOs (−3.46 eV to −3.54 eV) align closely with experimental calculations (−3.45 eV to −3.48 eV), indicating the potential of these dyes as electron acceptors. Furthermore, the alignment of frontier molecular orbital (FMO) values supports their suitability for electron acceptance. When applied to wool, silk, and polyester materials, these dyes confer UV protection properties, with wool-dyed fabrics achieving a UV Protection Factor (UPF) of 50+. Additionally, these dyes exhibit significantly improved nonlinear optical responses, with beta (β) values ranging from 11 × 10 to 23 × 10 esu and gamma (γ) values ranging from 275 × 10 to 365 × 10 esu, indicating their functionality as nonlinear optical materials.

中文翻译：

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氮萘酰亚胺染料的合成、理化、非线性光学性能：羊毛、丝绸、涤纶的染色及防紫外线性能


本研究重点是使用萘酚 AS、ASD 和 ASTR 偶联剂合成和表征三种偶氮萘酰亚胺染料 APAS、APASD 和 APASTR。该研究还观察到 DMSO 溶液中存在腙互变异构体。通过光谱分析对其进行表征，在 13C NMR 谱中显示出三个特征羰基碳峰。计算出的低 LUMO（-3.46 eV 至 -3.54 eV）与实验计算（-3.45 eV 至 -3.48 eV）密切相关，表明这些染料作为电子受体的潜力。此外，前沿分子轨道（FMO）值的排列支持它们适合电子接受。当应用于羊毛、丝绸和聚酯材料时，这些染料具有紫外线防护性能，羊毛染色织物的紫外线防护系数 (UPF) 达到 50 以上。此外，这些染料表现出显着改善的非线性光学响应，β (β) 值范围为 11 × 10 至 23 × 10 esu，gamma (γ) 值范围为 275 × 10 至 365 × 10 esu，表明它们具有非线性光学功能。材料。