Abstract
The study presents the influence of structure modulation by introduction of selected donor and acceptor substituents on the properties of 6-(1H-benzimidazole)-2(2,4-dinitrobenzenesulfonate)naphthalene used in thiophenol identification. The presence of –OH and –OR groups enhances the non-linear optics (NLO) response of the marker. The –NO2 substituent maximizes the non-linear response and increases the amount of transferred charge and the charge-transfer distance. The introduction of the –OH, –NO2 and –CN groups into the marker structure significantly improves the solubility and optical availability. The –NO2 group however contributes to mutagenicity and carcinogenicity. The –OH and –OR groups can be successfully used in bioimaging to detect specific molecules containing the –SH group in their structure. At the same time, the –OR group minimizes the energy barrier necessary to break the bond between the chromophore and the linker. The paper also includes a comparison of optical and biological properties of structures before and after identification of thiophenols.
Highlights
Thiophenols are widely used in the synthesis of many industrial products, primarily polymers, pesticides and pharmaceutical products.[1,2] Despite their widespread use, they are highly toxic and the average lethal dose (LC50) for sh is only 0.01– 0.04 mM.[3]
It has been demonstrated that the used donor–acceptor substituents (D/A) substituents do not signi cantly affect the position of HOMO–LUMO orbitals and only slightly affect the EGAP value
It has been shown that the –NO2 substituent increases the amount of transferred charge and the charge-transfer distance
Summary
Thiophenols are widely used in the synthesis of many industrial products, primarily polymers, pesticides and pharmaceutical products.[1,2] Despite their widespread use, they are highly toxic and the average lethal dose (LC50) for sh is only 0.01– 0.04 mM.[3]. Exposure of the human body to these compounds results in many serious illnesses, including polyposis, nausea, vomiting, muscle weakness and in special cases even death.[4,5] Against this background, it is important to search for new solutions for the easy and quick detection of thiophenols, especially in pharmaceuticals and in biological material. In this context, uorescent probes, which are dyes relatively easy to manufacture with a wide spectrum of Stokes shi s, have become of practical importance. Hand, it allows the creation of a uorescent probe operating in a speci c absorption and uorescence range, depending on the research requirements
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