New Fast, Highly Selective Probe with Both Aggregation-Induced Emission Enhancement and Intramolecular Charge-Transfer Characteristics for Homocysteine Detection

Abstract

A new fluorescence probe 2-(4′-(diphenylamino)-[1,1-biphenyl]-4-yl)-2H-[1,2,3]-triazole-4-carbaldehyde (DBTC) was designed and synthesized through Suzuki coupling reaction between (4-(diphenylamino)phenyl)boronic acid and (4-bromophenyl)-2H-[1,2,3]-triazole-4-carbaldehyde. This probe DBTC had intramolecular charge transfer and aggregation-induced emission enhancement performances and showed high selectivity and sensitivity toward homocysteine (Hcy) in the presence of other amino acids. The detection limit of probe DBTC for Hcy was 3.05 × 10 −6 M, and the mechanism was researched by 1 H NMR titration experiments and mass spectrometry. Furthermore, cell-culture results indicated that probe DBTC was cell permeable and could be used to detect Hcy in living cells. The good characteristics of the probe DBTC had huge application potential use for researching the effects of Hcy in other biological systems.

Highly Selective and Sensitive Sulfonylhydrazone Type Fluorescent Probe for Rapid Detection of Mercury(II) and Its Application in Logic Gate and Adsorption

“…And the linear regression equation was y = À 22.88x + 865.6 (R 2 = 0.9982). Based on the 3σ/k, [40][41][42][43][44] the lowest detection limit (LOD) of BS for Hg 2 + was found to be 2.84 × 10 À 8 M. Excellent linear correlation and low detection limit indicated that BS could not only qualitatively detect Hg 2 + , but also quantitatively detect Hg 2 + in a certain concentration range.…”

“…The triphenylamine unit has a unique propeller structure, excellent electron donating ability and easy-to-modify molecular structure, so it can be used as a luminescent group for small molecule fluorescent probes. Based on the previous work of our laboratory, [40][41][42][43][44][45][46][47][48][49][50][51][52] in this paper, triphenylamine was used as the fluorescent group, and the thiophene ring was introduced to modify it through Suzuki coupling reaction, which greatly increased the conjugation degree of triphenylamine and the electron donating ability allowed it to have better optical properties. Then, through condensation with benzenesulfonyl hydrazide, the Schiff base structure was introduced to enhance the coordination ability with Hg 2 + , to achieve the purpose of high selectivity and rapid detection.…”

An Intramolecular Charge Transfer and Aggregation Induced Emission Enhancement Fluorescent Probe Based on 2‐Phenyl‐1,2,3‐triazole for Highly Selective and Sensitive Detection of Homocysteine and Its Application in Living Cells

“…Based on previous works in our group, and other thiol‐ based fluorescent probes reported, one simple procedure was proposed to synthesize APTC with simple structure via Suzuki coupling reaction by combining 2‐phenyl‐1,2,3‐triazole with an anthracene group. The fluorescence characteristics was studied.…”

Highly selective and sensitive fluorescent probe possessing AIEE and ICT properties for rapid detection of Pb2+ in aqueous medium and its applications in living cells

“…Schiff bases contain C=N bands that show strong binding affinities for metal ions and the synthesis steps are relatively simple. Based on this research and combined with the previous work of our team, [ 27–41 ] we designed and synthesized a novel benzenesulfonyl hydrazone, the highly efficient fluorescent probe DBTBH , using the condensation reaction of aldehydes and benzenesulfonyl hydrazide for the selective and sensitive detection of Pb 2+ in highly aqueous media and without any interference from other metal cations and anions. As far as we know, this is the first time that the structure of benzenesulfonyl hydrazone has been reported as a fluorescent probe.…”