Dopamine recognition using Quinone–Hydroquinone calix[4]arene dimer

Subject Areas :

فروزنده رزاقیان ¹ , سعید تقوایی گنجعلی ² , محمد محمودی هاشمی ³ , رضا زادمرد ⁴ , شهرام مرادی دهقی ⁵

1 - دانشجوی دکترای شیمی آلی، گروه شیمی، واحد علوم وتحقیقات، دانشگاه آزاد اسلامی، تهران، ایران
2 - استاد شیمی آلی، گروه شیمی، واحد تهران شمال، دانشگاه آزاد اسلامی، تهران، ایران
3 - استاد شیمی آلی، گروه شیمی، واحد علوم وتحقیقات، دانشگاه آزاد اسلامی، تهران، ایران
4 - دانشیار شیمی آلی، پژوهشگاه شیمی ومهندسی شیمی ، تهران، ایران
5 - دانشیار شیمی آلی، گروه شیمی، واحد تهران شمال، دانشگاه آزاد اسلامی، تهران، ایران

Received: 2018-05-15 Accepted : 2018-10-17 Published : 2019-02-20

Keywords: Dopamine, Calix[4]arenes, Calix[4]arene dimers, Calixquinones, Recognition of biologically active molecules,

Abstract :

In this research, with a new strategy and convenient conditions, a novel bridgeless calix dimer was synthesised. Quinone- Hydroquinone calix[4]arene (4) was synthesised from calixquinone derivative in the presence of copper (II) acetate and 1,4- diaminobutane. The obtained dimer structure was characterised by various spectroscopic methods such as 1H-NMR, 13C-NMR, and IR spectroscopies. Since the macrocyclic molecules and in particular, calix[4]arene macrocycle derivatives, have wide usage as suitable receptors for recognising natural molecules. So, the synthesized compound was used. Also, the sole role of dopamine in central nervous and cardiovascular systems made it to be chosen as a guest molecule. The formation complex constant between Quinone-Hydroquinone calix[4]arene (4) as host and dopamine (guest) was calculated by fluorescence spectroscopy. The results indicated that the synthesized dimer (4) had not only a good ability to be the selective recognition of dopamine but also an appropriate repeatability.

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