PrismaSens

Organic water-contaminants (OWCs), such as PAHs, PFAS, HCB and hydrophilic OWCs, can cause adverse ecological and human health effects. Consequently, action is urgently needed for prevention of these pollutants, thus limiting OWCs possible risk to health and environment and guaranteeing healthy freshwater and seas. These actions require constant and real time environmental monitoring for the fast and selective pollutants detection, thus leading to an increasing demand of portable and even wearable sensing devices. In fact, OWCs are typically present in very low concentrations and in complex mixtures, then requiring a sensitive and selective detection. Chromatographic methods combined with mass spectrometry are frequently employed for the qualitative and quantitative detection of OWCs, allowing to achieve high sensitivity and selectivity. However, they are limited by the necessity for large and expensive analysis equipment, which cannot be employed “on site”, and of specialized workers, being thus inappropriate for remote monitoring of environment and water pollution. As a result, there is still a need for trustworthy, adaptable, and cost-effective techniques. Among the OWCs, pesticides and drugs are often chiral and can be found in water in optically active form. In fact, even if they are usually marketed as racemic mixtures, recent studies have shown that degradation of chiral organic water contaminants is often enantioselective, giving rise to scalemic, enantiomerically enriched mixtures. Moreover, enantiomers of chiral compounds often have different distribution fate, bioaccumulation potential, and toxicity. It follows that fast determination of the absolute configuration and enantiomeric excess (ee) of chiral pollutants in the environment is important for accurate environmental and human health risk assessment. Thus, optical chirality sensing employing host-guest chemistry coupled with detection through chiroptical spectroscopies would be affordable and suitable for high-throughput screening approach.

Aim of the PrismaSens project will be the development of novel supramolecular chemosensors based on host-guest recognition processes for the monitoring of OWCs in complex matrices.
In this project, we will focus our attention on a limited number of OWC targets, which give rise to particular concern not only in the densely populated southern regions, like Campania region, in industrial areas such that of Porto Torres in Sardinia and in other parts of Italy and the rest of the world. The targets have been chosen among those emerging water contaminants that still miss established and fast analytical detection methods.
In addition, PrismaSens project will focus attention on the use of a novel class of chiral macrocycles named prism[n]arenes, as fluorescent receptors for the design of novel chemosensors for the detection and the monitoring of OWCs.

Under the Influence of Water: Molecular Recognition of Organic Hydrophilic Molecules in Water with a Prismarene Host Driven by Hydration Effects

Chem. Eur. J. 2024, 30(44), e202401734

Chirality Sensing of Cryptochiral Guests with Prism[n]arenes

Chem. Eur. J. 2024, 30(40), e202401625