Perylene diimide (PDI) and naphthalene diimides (NDIs) are compounds widely used in supramolecular structures due to their versatile and functional properties. They have high absorptions and photoluminescence capabilities, which make them ideal for electronic transition studies. Reflux method, a widely employed synthetic technique, was utilized to synthesize NDI and PDI derivatives. In this method, the respective amino acids and NTDA (naphthalene-1,4,5,8-tetracarboxylic dianhydride) were combined in acetic acid and the resulting mixture was subjected to reflux. This study centered on a diverse set of NDI and PDI ligands, comprising L-ala-NDI, B-ala-NDI, Gly-NDI, Imi-NDI, Pyr-NDI, L-ala-PDI, B-ala-PDI, Gly-PDI, Imi-PDI, and Pyr-PDI ligands. Crystal structures were obtained for three NDI ligands, while the characterization of all ligands involved several analytical techniques such as NMR, IR, UV, DFT, TD-DFT calculations, and single-crystal x-ray crystallography specifically for the NDI ligands. The investigation focused on studying the electron acceptor/donor behavior of the NDI and PDI ligands, identifying their potential for charge transfer applications. Furthermore, the NLO (nonlinear optical) response of all 10 NDI and PDI ligands was assessed through an analysis involving HOMO-LUMO, TDM, EDDM, NCI, Iso-surface, MEP, natural population, and DOS analysis. This evaluation encompassed the examination of linear polarizability, as well as first and second hyperpolarizability in the context of NLO. The findings of the study revealed that Gly-PDI, Imi-PDI, L-ala-PDI, and B-ala-PDI ligands displayed a higher NLO response compared with the other ligands. These results highlight the potential of these ligands for nonlinear optical applications. The comprehensive characterization and assessment of the NDI and PDI ligands contribute to a deeper understanding of their electron properties, positioning them as promising candidates for charge transfer and nonlinear optical materials.

中文翻译：

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通过计算方法综合分析萘和苝二酰亚胺衍生物的电子跃迁

苝二酰亚胺（PDI）和萘二酰亚胺（NDI）由于其多功能和功能特性而广泛用于超分子结构。它们具有高吸收和光致发光能力，这使得它们成为电子跃迁研究的理想选择。回流法是一种广泛采用的合成技术，用于合成NDI和PDI衍生物。在该方法中，将各氨基酸和NTDA(萘-1,4,5,8-四甲酸二酐)在乙酸中混合，并将所得混合物进行回流。本研究以多种 NDI 和 PDI 配体为中心，包括 L-ala-NDI、B-ala-NDI、Gly-NDI、Imi-NDI、Pyr-NDI、L-ala-PDI、B-ala-PDI、 Gly-PDI、Imi-PDI 和 Pyr-PDI 配体。获得了三种 NDI 配体的晶体结构，而所有配体的表征涉及多种分析技术，例如 NMR、IR、UV、DFT、TD-DFT 计算以及专门针对 NDI 配体的单晶 X 射线晶体学。该研究的重点是研究 NDI 和 PDI 配体的电子受体/供体行为，确定它们在电荷转移应用中的潜力。此外，通过涉及 HOMO-LUMO、TDM、EDDM、NCI、Iso-surface、MEP、自然群体和 DOS 分析的分析，评估了所有 10 个 NDI 和 PDI 配体的 NLO（非线性光学）响应。该评估包括检查线性极化率以及 NLO 背景下的第一和第二超极化率。研究结果表明，与其他配体相比，Gly-PDI、Imi-PDI、L-ala-PDI 和 B-ala-PDI 配体表现出更高的 NLO 响应。这些结果凸显了这些配体在非线性光学应用中的潜力。NDI 和 PDI 配体的全面表征和评估有助于更深入地了解它们的电子特性，使它们成为电荷转移和非线性光学材料的有前途的候选材料。