Herein, we report
the synthesis and characterization of a chemosensor, 5-(diethylamino)-2-(2,3-dihydro-1
H
-perimidin-2-yl)phenol (H
L
), synthesized from
a condensation between 4-(diethylamino)salicylaldehyde and 1,8-diaminonaphthalene.
Upon investigation of the sensing properties of H
L
, it
was found that this sensor may be employed for simple yet efficient
detection of Cu
2+
in aqueous methanol solutions. The selective
and ratiometric response to Cu
2+
yielded an outstandingly
low limit of detection of 3.7 nM by spectrophotometry and is also
useful as a naked-eye sensor from 2.5 μM. The system was studied
by spectrophotometric pH titrations to determine Cu
2+
binding
constants and complex speciation. Binding of Cu
2+
to H
L
occurs in 1:1 stoichiometry, in good agreement with high-resolution
electrospray ionization mass spectrometry (ESI-HRMS) results, Cu
2+
titrations, and Job’s plot experiments, while the
coordination geometry was tentatively assigned as square pyramidal
by spectroscopic studies.