Hydrazone-based switches, metallo-assemblies and sensors

Abstract

The hydrazone functional group has been extensively studied and used in the context of supramolecular chemistry. Its pervasiveness and versatility can be attributed to its ease of synthesis, modularity, and most importantly unique structural properties, which enable its integration in different applications. This review provides an overview of the utilization of hydrazones in three supramolecular chemistry related areas: molecular switches, metallo-assemblies and sensors. These topics were chosen because they highlight the diversity of hydrazones, and emphasize their uniqueness vis-à-vis the imine functional group. Discussion entails (i) chemical and light activated switching of hydrazones, and how this can be used in controlling the properties of self-assembled systems, (ii) the use of hydrazones in the formation of dynamic and stimuli responsive metallogrids, and (iii) the use of hydrazones in detecting metal cations (Zn(2+), Cu(2+), Hg(2+), etc.), anions (F(-), CN(-), P2O7(4-), etc.) and neutral molecules (amines, water, Cys, etc.).

Enzi̇mati̇k Oksi̇dati̇f Poli̇meri̇zasyon İle Orto-Hi̇drazon-Fonksi̇yonlu Oli̇gofenol Sentezi̇

“…Hidrazon fonksiyonel grup içeren bileşiklerin endüstride çok çeşitli alanlarda kullanıldığından bahsetmiştik [13]. Elde ettiğimiz hidrazon grubu içeren oligomerler bu anlamda önem taşımaktadır.…”

“…Hidrazon fonksiyonel grup içeren bileşikleri, organik sentezler, biyomedikal uygulamalar, supramoleküler kimya, metal kovalent bağlı organik yapılar, ilaç salınım sistemleri uygulamaları, dinamik kombinasyon kimyası, boya ve boşluk transfer malzemeleri gibi çeşitli alanlarda bolca kullanmışlardır [13]. Hidrazon grubuı içeren polimerleri ilaç salınım sistemlerinde yaygın bir şekilde kullanmışlardır.…”

A New Optical Sensor for Selective Monitoring of Nickel Ion Based on A Hydrazone Derivative Immobilized on the Triacetyl Cellulose Membrane

“…Deionized double-distilled water was used throughout and test solutions were buffered in a 0.02 mol L -1 solution of acetic acid/ sodium acetate and pH adjusted with dropwise addition of 1 mol L -1 solution of HCl or NaOH. The Schiff's base L, with the chemical name of 1-acenaphthoquinone 1-thiosemicarbazone, was synthesized and purified using a previously reported method [27,28].…”

“…In the present study, a hydrazone derivative ligand 1-acenaphthoquinone 1-thiosemicarbazone, L (Figure 1) [27,28], is covalently immobilized on a triacetyl cellulose membrane to be used as an effective ionophore with N and O donor atoms for construction of a selective optical sensor for the spectrophotometric determination of Ni 2+ in aqueous solutions. The studied compound as an ionophore is the family of hydrazone which is a kind of asymmetric Schiff's base.…”

Spectral characterization and DNA binding properties of lanthanide(III) complexes with 2-acetylpyridine isonicotinoylhydrazone (APINH)

“…Hence, the synthesis of and characterization of newer lanthanide complexes is a potential field of research in inorganic chemistry. Though Sacconi has reported [12] lanthanide complexes of acetylacetone isonicotinoyl hydrazone in the year 1954, a literature review [13][14][15] indicated that the study of such complexes is relatively less when compared with transition metal complexes with this class of ligands.…”