Abstract
A rational approach to the synthesis of substituted naphtho[1,8-ef]perimidines based on SNH methodology and cyclization reaction in the series of condensed azines with naphthalene substituents was presented. Photophysical properties of the obtained fluorophores were studied, in particular, green fluorescence in the 485–536 nm range with quantum yield up to 32.4% was detected. HOMO-LUMO energy values and distributions for the new compounds were calculated by the DFT method in comparison with nitroanalytes and perylene. Based on the data obtained, as well as on the results of fluorescence titration, the possibility of using the new diazaperylenes as potential chemosensors for the visual detection of nitro-containing explosives was shown.
Highlights
Polyaromatic compounds are widely used as various types of chemosensors, including ones for the detection of nitrocontaining explosives
It is known that the presence of pyridine nitrogen atom in the structure of polycyclic aromatic hydrocarbons can significantly enhance the susceptibility of such structures to the action of nucleophilic agents, thereby opening the possibility of using the SNH methodology for its functionalization [6, 7]
The aza-heterocycles obtained by this approach can serve as a basis for synthesis of more efficient chemosensors by combining π-conjugated and fluorophore fragments into one molecule for the enhancement of its sensory properties, e.g. towards nitroanalytes, by the creation of π-conjugated donor-acceptor systems [1]
Summary
Polyaromatic compounds are widely used as various types of chemosensors, including ones for the detection of nitrocontaining explosives. This is achieved by preferential formation of π-complexes between the sensor and quencher due to high π-deficiency of the latter, as well as hydrogen bonding due to participation in interaction with nitroaromatic analytes of functional groups on the periphery of the chemosensor and formation of inclusion complexes. The aza-heterocycles obtained by this approach can serve as a basis for synthesis of more efficient chemosensors by combining π-conjugated and fluorophore fragments into one molecule for the enhancement of its sensory properties, e.g. towards nitroanalytes, by the creation of π-conjugated donor-acceptor systems [1]. In this work we propose a methodology for the synthesis of new fluorophores based on naphtho[1,8ef]perimidine and studying their ability to use for visual detection of nitro-containing analytes
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