Abstract
2,3-Diaminomaleonitrile (DAMN) has proved to be a valuable organic π-conjugated molecule having many applications in the area of chemosensors for sensing of ionic and neutral species because of its ability to act as a building block for well-defined molecular architectures and scaffolds for preorganised arrays of functionality. In this article, we discussed the utilization of 2,3-diaminomaleonitrile (DAMN) for the design and development of chemosensor molecules and their application in the area of metal ion, anion and reactive oxygen species sensing. Along with these, we present different examples of DAMN based chemosensors for multiple ion sensing. We also discuss the ion sensing mechanism and potential uses in other related areas of research.
Highlights
The design and development of chemosensor molecules mainly rely on the concepts of complementarity, co-cooperativity and preorganization.1–3 Sensor molecules derived from these concepts have a suitable orientation of functional groups which produce strong covalent and non-covalent interactions between sensors and target guest species.4–6 Different scaffolds like calixarenes, cyclotriveratrylene, cyclodextrin, borondipyrromethene (BODIPY), naphthalimides, crown-ethers/thiacrown-ethers, resorcinarenes etc. were successfully used for designing chemosensor molecules for sensing of speci c ions and neutral species
The electron-donating DAMN binds with cation which inhibit intramolecular charge transfer (ICT) due to the loses of electron-donating ability of DAMN and make the sensor cation adduct uorescent
This review demonstrates how the eld of DAMN based chemosensor research have ourished over a period of last 25 years
Summary
The design and development of chemosensor molecules mainly rely on the concepts of complementarity, co-cooperativity and preorganization. Sensor molecules derived from these concepts have a suitable orientation of functional groups which produce strong covalent and non-covalent interactions between sensors and target guest species. Different scaffolds like calixarenes, cyclotriveratrylene, cyclodextrin, borondipyrromethene (BODIPY), naphthalimides, crown-ethers/thiacrown-ethers, resorcinarenes etc. were successfully used for designing chemosensor molecules for sensing of speci c ions and neutral species. The shi in absorption maxima was explained by the deprotonation of NH2 of DAMN coupled with intermolecular charge transfer led to enhancement of donor-toacceptor ICT transition (Fig. 5) They examined the sensitivity of sensor [3] towards other anions such as H2PO4À, NO3À, AcOÀ, FÀ, ClÀ, BrÀ and IÀ but none of these ions showed any responses in absorption, emission spectrum and colorimetric sensing. Another DAMN derived biocompatible duel channel probe [4] was synthesized from hydroxyl benzothiazole moiety and 2,3-diaminomaleonitrile for selective detection of toxic CNÀ ions in 50% aqueous DMF.. Scheme 1 General approach for sensing of analytes by DAMN derived sensor molecules
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