Imine Formation as a Simple Reaction to Construct Copper-Reactive Cruciform Fluorophores

Abstract

We developed a series of new conjugated cruciform fluorophores (XF) featuring imine groups. The condensation of an XF containing aldehyde functionalities and selected primary amines leads to several XF-imine derivatives. Upon addition of Cu(2+) or Zn(2+) ions to solutions of the imine XFs in different solvents, a red-shifted emission is detected, resulting in an altered emission color. The imine acts as a simple modular metallo-reactive fluorophore.

Water-Soluble Cruciforms and Distyrylbenzenes: Synthesis, Characterization, and pH-Dependent Amine-Sensing Properties

“…The combined organic layers were dried over MgSO 4 , and the solvents were evaporated. (14). Under a nitrogen atmosphere tetraethyl ((2,5-diiodo-1,4-phenylene)bis(methylene))bis(phosphonate) (10b; 4.00 g, 6.35 mmol) was dissolved in dry THF (50 mL) and cooled to 0 °C.…”

“…The imines can be made and easily isolated, being sensory materials in their own right. 14 Here we have expanded our structural base and investigated water-soluble XFs and DSB-appended aldehydes as amine sensors.…”

“…The observed detection limit for the dialdehydes was considerably lower than that reported for the tetrahydroxy-XFs. The imines can be made and easily isolated, being sensory materials in their own right . Here we have expanded our structural base and investigated water-soluble XFs and DSB-appended aldehydes as amine sensors.…”

Amine Detection with Distyrylbenzenedialdehyde-Based Knoevenagel Adducts

“…We have developed a sensor, or better dosimeter platform, with the water-soluble DSB-dialdehyde 1 , which detects amines in water and in vapors when sprayed onto a solid surface. The detection scheme rests on the conversion of the dialdehyde into a bis-imine or into a bis-aminal, when diamines, such as propylenediamine or ethylenediamine, are the model analytes, which are detected at concentrations of less than 1 mM L –1 in water . While 1 and its alkoxy derivatives have been fairly successful as amine dosimeters, we want to modulate the amine sensing capabilities of 1 by postfunctionalization.…”

A selective fluorescence probe for copper(II) ion in aqueous solution based on 4-(1,4,5-triphenyl-1H-imidazol-2-yl)anilinyl acetates

“…Fluorescent probes display a significant change in optical signal when they selectively sense the chemical [1][2][3] and biological [4,5] guest species, especially for metal ions of biological interest. Among the metal ions, the divalent form of copper, Cu 2?…”