Size-matching Recognition of Biogenic Amines by Water-soluble Terphen[3]arene: Toward Visual Detection of Food Spoilage

Convenient and efficient detection of biogenic amines (BAs) is crucial for ensuring food safety and quality, as well as for the diagnosis and treatment of diseases. In this study, terphen[3]arene macrocycle TP3 was designed and synthesized by skeleton extension, and further portal functionalized into the water-soluble derivative WTP3. Containing twelve carboxylation moieties and a medium-sized π-rich cavity, WTP3 showed good water solubility and host-guest performance with various aliphatic amines. Meanwhile, WTP3 exhibited excellent association affinities for aliphatic amines with large spatial sizes, such as 1,4-butanediamine (1,4-BDA), 1,5-pentanediamine (1,5-PDA), cyclohexylamine (CHA), di-n-butylamine (DBA) and tri-n-propylamine (TPA). Finally, a WTP3-based smart label and portable detection device were constructed and successfully employed for the detection of aliphatic amines generated during food spoilage. With the help of AI technology, quantitative detection for aliphatic amines were expected to be further applied on intelligent packaging labels for food freshness.