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一种基于邻苯二甲腈二聚体的新型铁离子选择性荧光化学传感器:合成、分析及理论研究

A novel selective fluorescent chemosensor for Fe ions based on phthalonitrile dimer: synthesis, analysis, and theoretical studies.

作者信息

Al-Raqa Shaya, ÖmeroĞlu İpek, Erbahar Doğan, DurmuŞ Mahmut

机构信息

Department of Chemistry, Faculty of Science, Taibah University, Al-Madinah Al Munawarah Saudi Arabia.

Department of Chemistry, Faculty of Basic Sciences, Gebze Technical University, Kocaeli Turkey.

出版信息

Turk J Chem. 2020 Oct 26;44(5):1254-1264. doi: 10.3906/kim-2004-68. eCollection 2020.

Abstract

Phenyl-4,4-di(3,6-dibutoxyphthalonitrile) ( ) was synthesized by the reaction of 1,4-phenylenebisboronic acid ( ) and 4-bromo-3,6-dibutoxyphthalonitrile ( ), using Suzuki cross-coupling reaction. The newly synthesized compound ( ) was characterized by FT-IR, MALDI-MS, ESI-MS, H-NMR, C-NMR, and C-DEPT-135-NMR. The fluorescence property of phenyl-4,4-di(3,6-dibutoxyphthalonitrile) ( ) towards various metal ions was investigated by fluorescence spectroscopy, and it was observed thatthe compound ( ) displayed a significantly 'turn-off' response to Fe , which was referred to 1:2 complex formation between ligand ( ) and Fe . The compound was also studied via density functional theory calculations revealing the interaction mechanism of the molecule with Fe ions.

摘要

通过1,4-亚苯基双硼酸与4-溴-3,6-二丁氧基邻苯二甲腈发生铃木交叉偶联反应合成了苯基-4,4-二(3,6-二丁氧基邻苯二甲腈)。通过傅里叶变换红外光谱、基质辅助激光解吸电离质谱、电喷雾电离质谱、氢核磁共振、碳核磁共振和碳-DEPT-135-核磁共振对新合成的化合物进行了表征。通过荧光光谱研究了苯基-4,4-二(3,6-二丁氧基邻苯二甲腈)对各种金属离子的荧光性质,观察到该化合物对Fe³⁺表现出显著的“关断”响应,这归因于配体与Fe³⁺形成了1:2的配合物。还通过密度泛函理论计算对该化合物进行了研究,揭示了该分子与Fe³⁺离子的相互作用机制。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a715/7751899/a1dcff55842f/turkjchem-44-1254-sch001.jpg

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