Current Organic Synthesis - Volume 20, Issue 1, 2023

The analysis of amines has long been a very important task in science, industry, and healthcare. To date, this task has been accomplished by using expensive and time-consuming methods. Colorimetric and fluorescent chemodosimeters enable the fast, accurate, and sensitive analysis of various species with inexpensive instruments or the naked eye. Accordingly, the studies on these probes have gained great momentum in the last 20 years. In this review, amine chemodosimeters developed in the last 10 years were investigated. The investigated chemodosimeters are metal-free structures based on small organic compounds. The strategies for the detection, differentiation, and quantification of amines were discussed by considering the reaction types.

Aza-boron-dipyrromethenes (Aza-BODIPYs) represent an important class of chromophores absorbing and emitting in the near-infrared (NIR) region. They have unique optical and electronic features and higher physiological and photo stability than other NIR dyes. Especially after the development of facile synthetic routes, Aza-BODIPYs have become indispensable fluors that can find various applications ranging from chemosensors, bioimaging, phototherapy, solar energy materials, photocatalysis, photon upconversion, lasers, and optoelectronics. Herein, we review Aza-BODIPY based fluorescent and colorimetric chemosensors. We show the potential and untapped toolbox of Aza-BODIPY based fluorescent and colorimetric chemosensors. Hence, we divide the fluorescent and colorimetric chemosensors and probes into five sections according to the target analytes. The first section begins with the chemosensors developed for pH. Next, we discuss Aza-BODIPY based ion sensors, including metal ions and anions. Finally, we present the chemosensors and probes concerning reactive oxygen (ROS) and nitrogen species (RNS) along with biologically relevant species in the last two sections. We believe that Aza-BODIPYs are still in their infancy, and they have a promising future for translation from the bench to real biomedical and materials science applications. After two decades of intensive research, it seems that there are many more to come in this already fertile field. Overall, we hope that future work will further expand the applications of Aza-BODIPY in many areas.

Cyanide anion has wide use in industrial areas; however, it has a high toxic effect on the environment as waste. Moreover, plant seeds contain cyanide that is often consumed by human beings. Therefore, many studies are carried out to determine cyanide. Especially, optical sensors showing colorimetric and fluorimetric changes have been of considerable interest due to their easy, cheap, and fast responses. This review discusses recent developments in the colorimetric and fluorimetric detection of cyanide by nucleophilic addition to different types of receptors via the chemodosimeter approach. The sensitivity and selectivity of the sensors have been reviewed for changes in absorption and fluorescence, naked-eye detection, real sample application, and detection limits when interacting with cyanide.

Advances in molecular probes have recently intensified because they are valuable tools in studying species of interest for human health, the environment, and industry. Among these species, cyanide (CN-) and fluoride (F-) stand out as hazardous and toxic ions in trace amounts. Thus, there is a significant interest in probes design for their detection with diverse diazoles (pyrazole and imidazole) used for this purpose. These diazole derivatives are known as functional molecules because of their known synthetic versatility and applicability, as they exhibit essential photophysical properties with helpful recognition centers. This review provides an overview of the recent progress (2017-2021) in diazole-based sensors for CN- and F- detection, using the azolic ring as a signaling or recognition unit. The discussion focuses on the mechanism of the action described for recognizing the anion, the structure of the probes with the best synthetic simplicity, detection limits (LODs), application, and selectivity. In this context, the analysis involves probes for cyanide sensing first, then probes for fluoride sensing, and ultimately, dual probes that allow both species recognition.

Apurinic and apyrimidinic sites, also referred to as abasic or AP sites, are residues of duplex DNA in which one DNA base is removed from a Watson-Crick base pair. They are formed during the enzymatic repair of DNA and offer binding sites for a variety of guest molecules. Specifically, the AP site may bind an appropriate ligand as a substitute for the missing nucleic base, thus stabilizing the abasic site-containing DNA (AP-DNA). Notably, ligands that bind selectively to abasic sites may be employed for analytical and therapeutical purposes. As a result, there is a search for structural features that establish a strong and selective association of a given ligand with the abasic position in DNA. Against this background, this review provides an overview of the different classes of ligands for abasic site-containing DNA (AP-DNA). This review covers covalently binding substrates, namely amine and oxyamine derivatives, as well as ligands that bind to AP-DNA by noncovalent association, as represented by small heterocyclic aromatic compounds, metal-organic complexes, macrocyclic cyclophanes, and intercalator-nucleobase conjugates. As the systematic development of fluorescent probes for AP-DNA has been somewhat neglected so far, this review article contains a survey of the available reports on the fluorimetric response of the ligand upon binding to the AP-DNA. Based on these data, this compilation shall present a perspective for future developments of fluorescent probes for AP-DNA.

Fluorescent bio-imaging will be the future in the medical diagnostic for visualising inner cellular and tissues. Near-infrared (NIR) emitting fluorescent probes serve dynamically for targeted fluorescent imaging of live cells and tissues. NIR imaging is advantageous because of its merits like deep tissue penetration, minimum damage to the tissue, reduced auto fluorescence from the background, and improved resolution in imaging. The Development of the NIR emitting probe was well explored recently and growing drastically. In this review, we summarise recent achievements in NIR probes in between 2018-2021. The merits and future applications have also been discussed in this review.