Fluorometric Sensing of Biogenic Amines with Aggregation‐Induced Emission‐Active Tetraphenylethenes

Abstract

A fluorometric sensor for detection and identification of biogenic amines with carboxylic acid modified tetraphenylethenes (TPEs) based on aggregation-induced emission (AIE) is reported. A mixture of the carboxylic acid substituted TPE and biogenic amines displayed a blue emission on aggregation, which serves as a "turn-on" fluorescent sensor for the amines, the degree of fluorescence enhancement being dependent on the amine. The chromic responses were utilized to distinguish the amines. A fluorometric sensor array of three TPEs with carboxylic acid groups was shown to identify accurately 10 different amines, including biogenic amines. The response patterns were systematically classified by using linear discriminant analysis (LDA) with 98% classification accuracy. Additional information on the concentration of histamine in a "tuna fish matrix" as an example was assessed by the further analysis of the fluorescence intensity, demonstrating a test for food freshness and quality.

AIE active pyridinium fused tetraphenylethene: Rapid and selective fluorescent “turn-on” sensor for fluoride ion in aqueous media

“…The first involves the formation of aggregated complex which induces a fluorescence enhancement due to the noncovalent interaction between analyte and AIE active luminogen. [35][36][37] The second strategy consists of the formation of the nonpolar fluorescent aggregates either by elimination of polar moieties on AIE active luminogen or by addition of analyte to the receptor. [38][39][40][41][42][43] In this study, we propose a novel sensing system for both fluoride ion sensing and AIE strategies in which the interaction of analyte leads to the formation of turn-on fluorescence due to the formation of least soluble aggregated salts by ion displacement process.…”

Recent progress in the development of advanced element-block materials

“…We were able to detect the amine derivatives, which show critical effects as a signal transducer or a stimulant drug, at concentrations under 1 μM, similar in sensitivity to conventional fluorescence probes. 52,53 It was expected that this system should be valid to monitor the distribution of bio-active molecules at cellular concentrations.…”

New Chemo-/Biosensors with Silole and Tetraphenylethene Molecules Based on the Aggregation and Deaggregation Mechanism

“…TPE derivatives 26 bearing two carboxylic acid groups were reported to aggregate and emit differently in the presence of a variety of biologically relevant amines (biogenic amines) [50]. The multivalent interactions including hydrogen-bonding and/or electrostatic interactions induced aggregation of 26 differently and biogenic amines could therefore be discriminated by the distinct fluorescence behavior of 26.…”