Synthesis and Characterization of Bis‐1,2,3‐Triazole Ligand and its Corresponding Copper Complex for the Development of Electrochemical Affinity Biosensors

Abstract

The bis‐triazole ligand and its corresponding copper complexes were synthesized and characterized for the first time and proposed as new labels for the development of electrochemical aptasensors. The bis‐triazole ligand was prepared from methyl 1,6‐heptadiyne‐4‐carboxylate and 2‐(azidomethyl)phenol using classical CuAAC in presence of different copper salts. The X‐ray structure of bis‐triazole showed a symmetry center (C1). UV‐Vis and X‐band EPR spectra showed that the coordination capacity of the bis‐triazole ligand was improved in the presence of triethylamine due to deprotonation of the triazole and phenolate moieties. After complexation with copper, the obtained complex was successfully attached to an anti‐estradiol aptamer through thiol‐maleimide coupling, and the resulting labelled aptamer was immobilized on a carbon screen‐printed electrode by carbodiimide coupling. The electrochemical response of the resulting sensor was shown to decrease in the presence of estradiol, demonstrating that the developed complexes can be applied for the development of aptasensors.

A pyrene–calix[4]triazolium conjugate for fluorescence recognition of hydrogen sulfate

“…The synthesis starts with the production of tri-triazole 1 via the 1,3-dipolar cycloaddition of a known azide 2 18 and alkyne 3 19 in the presence of a catalytic amount of Cu salt. The N , O -isopropylidene, and tert -butoxycarbonyl (Boc) groups of 1 were removed using trifluoroacetic acid (TFA) to convert 1 to the ammonium salt, which was treated with diazo-transfer reagent 4 20 to obtain azide 5 . Using this substrate, esterification with acyl chloride 6 21 afforded pyrenyl-tritriazole 7 , a precursor for cyclization.…”

New Volatile Perfluorinated Amidine–Carboxylate Copper(II) Complexes as Promising Precursors in CVD and FEBID Methods

“…Nowadays, copper compounds are used, for example, to design hybrid organicinorganic materials [1][2][3], anticancer agents [4,5], and sensors [6,7]. Additionally, copper complexes are used as model compounds and tested as antimicrobial agents [8][9][10].…”

Consecutive 2-azidoallylation/click cycloaddition of active methylene for synthesis of functionalized hepta-1,6-dienes with a bis-1,2,3-triazole scaffold

“…6 The above considerable achievements greatly promoted the utility of 1,2,3-triazoles in a wide range of fields including medicinal chemistry. As an alternative family, the bis-1,2,3-bistriazole derivatives have attracted increasing attention, exhibiting practicability 7 in the fields of supramolecular chemistry, medicinal chemistry, polymer chemistry, etc . Traditionally, the bis-1,2,3-triazole heterocyclic motif could be obtained either by using diacetylenes with azides or by using diazides with acetylenes through the CuAAC reaction.…”