Mahdy Abdulsalam, Zahra Jalal A, Haddadin Randa N, Kasabri Violet, A K Mohammed Ahmed, Mohamed Mohamed Gamal
Chemistry Department, School of Science, The University of Jordan, Amman 11942, Jordan.
Chemistry Department, Faculty of Education & Science-Rada'a, Albaydha University, Albaydha, Yemen.
ACS Omega. 2025 Aug 29;10(36):41878-41889. doi: 10.1021/acsomega.5c06164. eCollection 2025 Sep 16.
A series of aliphatic diamine-based naphthoxazine monomersdesignated as NZ-EDA, NZ-PDA, and NZ-HDAwere successfully synthesized via a one-pot Mannich condensation reaction involving 2-naphthol, paraformaldehyde, and three different aliphatic diamines: 1,2-diaminoethane, 1,3-diaminopropane, and 1,6-diaminohexane, respectively. Structural confirmation was achieved using FTIR and advanced NMR techniques (H, C, and DEPT-135). Unlike conventional naphthoxazine systems, the synthesized monomers exhibited markedly lower polymerization temperatures and a broader processing window, thereby enhancing their practical utility. Among the resulting polymers, poly-(NZ-PDA) exhibited the highest thermal stability, with a 10% weight-loss temperature ( ) of 367 °C. Photoluminescence analysis revealed intense blue emission across all monomers and their polymers, thanks to the molecular packing effects within the crystal structures, consistent with previous research findings. Morphological investigations via SEM showed that the NZ-EDA, NZ-PDA, and NZ-HDA monomers formed distinct spherical flower-like nanocrystals. The XRD results indicated that the average crystallite sizes of these monomers were 26, 15, and 20 nm, respectively. Their polymers exhibited a characteristic broad peak at 2θ ≈ 22.5°, indicating the formation of an amorphous structure that aligns with expectations. Biological assessments revealed that NZ-EDA and NZ-HDA exhibited potent anticandidal activities, with minimum inhibitory concentration values of 2 μg/mL against and 7.8 μg/mL against , respectively, but with low antibacterial activity. In comparison to substantially antioxidative vitamin C, NZ-PDA> NZ-EDA > NZ-HDA had the appreciable descending order of antioxidative DPPH radical scavenging capacities (with IC values 4.9 < 9.4 < 57.8 μM, respectively), but conversely, a considerable ascending order of antimicrobial properties. Any inferences of dual antioxidative-antimicrobial efficacies could not be established.
通过一锅法曼尼希缩合反应，成功合成了一系列基于脂肪族二胺的萘并恶嗪单体，分别命名为NZ-EDA、NZ-PDA和NZ-HDA，该反应涉及2-萘酚、多聚甲醛和三种不同的脂肪族二胺：1,2-二氨基乙烷、1,3-二氨基丙烷和1,6-二氨基己烷。使用傅里叶变换红外光谱（FTIR）和先进的核磁共振技术（氢谱、碳谱和DEPT-135）进行结构确认。与传统的萘并恶嗪体系不同，合成的单体表现出明显更低的聚合温度和更宽的加工窗口，从而提高了它们的实际应用价值。在所得的聚合物中，聚（NZ-PDA）表现出最高的热稳定性，其10%失重温度为367℃。光致发光分析表明，由于晶体结构中的分子堆积效应，所有单体及其聚合物都发出强烈的蓝色荧光，这与先前的研究结果一致。通过扫描电子显微镜（SEM）进行的形态学研究表明，NZ-EDA、NZ-PDA和NZ-HDA单体形成了独特的球形花状纳米晶体。X射线衍射（XRD）结果表明，这些单体的平均微晶尺寸分别为26、15和20纳米。它们的聚合物在2θ≈22.5°处呈现出一个特征性的宽峰，表明形成了符合预期的非晶结构。生物学评估表明，NZ-EDA和NZ-HDA表现出强大的抗念珠菌活性，对白色念珠菌和热带念珠菌的最低抑菌浓度值分别为2μg/mL和7.8μg/mL，但抗菌活性较低。与具有显著抗氧化作用的维生素C相比，NZ-PDA > NZ-EDA > NZ-HDA的抗氧化二苯基苦味酰基自由基清除能力呈明显的下降顺序（IC值分别为4.9 < 9.4 < 57.8μM），但相反，其抗菌性能呈显著的上升顺序。无法得出具有双重抗氧化-抗菌功效的结论。
