Chemosensor for the optical detection of aliphatic amines and diamines

Abstract

Two new chemosensor dyes with either one or two trifluoroacetophenone recognition moieties have been investigated in terms of reversibly interacting with amines and diamines.

Star‐Shaped Tripodal Chemosensors for the Detection of Aliphatic Amines

“…With multiple binding sites, Tripod-1 and Tripod-2 are theoretically assumed to form intramolecularly bridged hemiaminals with diamines (see our previous publication on a trifluoroacetyl-functionalized xanthene dye [13] ). However, for this study there are two reasons why bridged hemiaminals are not observed.…”

“…We recently reported on a xanthene dye with two trifluoroacetyl moieties that showed higher selectivity towards diaminoalkanes related to the monofunctionalized xanthene dye. [13] The preorganized arrangement of the two receptor groups in one molecule allowed diamine binding through macrocyAbstract: In this work, three new tripodal triphenylamine dyes are presented that are capable of reversibly binding amines and diamines to form hemiaminals through a covalent bond. The dyes were synthesized by the Heck reaction and possess stilbene units with one, two, or three trifluoroacetyl groups as receptor moieties.…”

Detection of Ethylenediamine Using a Fluorescent Probe in Solution and in a PMMA Matrix

“…The fluorescent organic probe exhibited high sensitivity and selectivity for ethylenediamine (ED) among various organic amine compounds both in solution and in a PMMA matrix. Because of widespread use of primary amines including ED in pharmaceutical industries, polymer industries, and dye manufacturing, it is highly demanding to develop new and efficient detection techniques for aliphatic amines [17].…”

Covalent Interactions in Chemosensor Design

“…This type of interaction has the advantage of being very strong, reversible, and functional in an aqueous or at least in a protic solvent. Quite a few optical sensors have been reported in recent years in this area [126][127][128][129][130][131][132][133][134][135][136][137][138][139][140][141]. In one specific example, (trifluoreacetyl) azobenzene dye (10, Scheme 3.3) was reported to change chromophoric properties upon reaction with an amine.…”

“…This is a high association constant for single-pair functional interactions and comparable to that of boronic acid-diol interactions. A series of derivatives of 10 have been developed for amine sensing based on optical property changes either in fluorescence or absorption [129][130][131]137]. These examples are shown in Fig.…”