Abstract
Novel 18- and 23-membered diazomacrocycles were obtained with satisfactory yields by diazocoupling of aromatic diamines with pyrrole in reactions carried under high dilution conditions. X-ray structure of macrocycle bearing five carbon atoms linkage was determined and described. Compounds were characterized as chromogenic heavy metal ions receptors. Selective color and spectral response for lead(II) was found in acetonitrile and its mixture with water. Complexation properties of newly obtained macrocycles with a hydrocarbon chain were compared with the properties of their oligoether analogs. The influence of the introduction of hydrocarbon residue as a part of macrocycle on the lead(II) binding was discussed. Selective and sensitive colorimetric probe for lead(II) in aqueous acetonitrile with detection limit 56.1 μg/L was proposed.
Highlights
Heavy metals—like lead(II)—are highly toxic to humans and bioaccumulate in aquatic systems having harmful effects on the environment [1,2,3]
The possibility of lead poisoning is mentioned in the case of famous composers Beethoven and Händel [4,5]
Lead poisoning is rarely seen in developed countries, but it still represents a major environmental problem in certain areas, in tap water in communities with older service lines and older household plumbing containing lead
Summary
Heavy metals—like lead(II)—are highly toxic to humans and bioaccumulate in aquatic systems having harmful effects on the environment [1,2,3]. Lead poisoning (saturnism) has been present throughout the history of mankind. Exposure to lead is often claimed to contribute to the fall of the Roman Empire. Mental disorders called “painter’s colic” or “painter’s madness” displayed by some of the great masters, including Michelangelo and Caravaggio, are attributed to lead poisoning. The possibility of lead poisoning is mentioned in the case of famous composers Beethoven and Händel [4,5]. Lead exposure causes dysfunction of blood and nervous systems. Lead is precipitating in the brain, kidneys and reproductive system. Poisoning with lead can cause anemia and brain damage and death [6,7,8]. The regulatory guidelines’ value given for drinking water by the WHO is 0.01 mg/L [9]
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