Design and syntheses of novel fluorescent organosilicon-based chemosensors through click silylation: detection of biogenic amines

Abstract

A concise and useful synthesis of novel 1,2,3-triazole based silatrane (TBS)-scaffolds (2a–e) in good yield from 1,2,3-triazole based triethoxysilane (TBTES)-linkers (1a–e) is described. Click silylation of terminal alkynes with γ-azidopropyltriethoxysilane (AzPTES) was used for the synthesis of TBTES-linkers (1a–e). The synthesized TBS-scaffolds (2a–e) were comprehensively characterized by ¹H and ¹³C NMR, mass spectrometry and single X-ray crystallographic studies. The broad scope of these TBS-scaffolds towards biogenic amines is explored by the use of a CH₃CN : H₂O (98 : 2; v/v) solvent system. The receptor 2c and 2d shows high affinity towards spermine and histamine, respectively. To the best of our knowledge, the present investigation represents the first report on the use of organosilicon-based chemosensors for the recognition of biogenic amines.