Synthesis of New Tetra Triazole Functionalized Calix[4]resorcinarene and Chemosensing of Copper Ions in Aqueous Medium

Abstract

A new tetra triazole functionalized calix[4]resorcinarene macrocycle (5) is synthesized and utilized for the detection of copper ions in the aqueous medium. The photophysical potential of compound (5) is examined by a range of cations (Ba2+, Ca2+, Co2+, Hg2+, K+, Mg2+, Mn2+, Na+, NH4 + and Pd2+). The triazole based calix[4]resorcinarene macrocycle (5) has interacted with Cu2+ ion in preference of other cations. A significant quenching has been observed after the addition of 15 μM Cu2+ ion solution, which produced 4.2 folds drift in the absorption intensity of compound (5). Tetra triazole functionalized calix[4]resorcinarene macrocycle showed high selectivity towards copper ion chemosensing without any interference in competitive studies. The pH studies of compound (5) with Cu2+ indicated the maximum chelation between 7- 7.5 pH. The compound (5) is capable to recognize Cu2+ at 1 μM detectable limit. Copper ion was detected in tap water with 15 μM concentration. Job’s plot showed 1:2 binding ratio between macrocycle (5) and Cu2+.

Copper(I)-Catalyzed Alkyne–Azide Cycloaddition (CuAAC) “Click” Reaction: A Powerful Tool for Functionalizing Polyhydroxylated Platforms

“…The macrocycle of calix[4]­resorcinarene based on triazole 68 interacts with the Cu 2+ ion in preference to other cations. This new tetratriazole compound 72 was synthesized from an aldehyde functionalized with an aliphatic chain 70 via click chemistry for a subsequent reaction with resorcinol 71 in an acid medium …”

“…This new tetratriazole compound 72 was synthesized from an aldehyde functionalized with an aliphatic chain 70 via click chemistry for a subsequent reaction with resorcinol 71 in an acid medium. 81 Biologically active molecules such as coumarin, 72 folic acid, 82 cyclodextrins, 76 and spiroindoline 3 have also been incorporated by means of click chemistry to these functionalized calixarene/resorcinarene-type platforms (Figure 7). These four derivatives were obtained under the same synthetic route of click chemistry, using Cu(I) generated in situ as a catalyst through the reaction of CuSO 4 •5H 2 O and sodium ascorbate, with rt temperature variation for 73, 74, and 76 assisted by MW for 75, all in a mixture of polar solvents.…”

“…This new tetratriazole compound 72 was synthesized from an aldehyde functionalized with an aliphatic chain 70 via click chemistry for a subsequent reaction with resorcinol 71 in an acid medium. 81 …”

Intramolecular Hydrogen Bond Driven Conformational Selectivity of Coumarin Derivatives of Resorcin[4]arene

“…Resorcin[4]arenes can be functionalised, especially at their upper rim, to provide selective structural, physical, and chemical properties [ 8 ]. Functionalised resorcin[4]arenes have been used in supramolecular host–guest (H–G) chemistry [ 9 ], nanoparticle synthesis [ 10 ], optical [ 11 ], chemosensors [ 12 ], and for separation applications [ 13 ]. Larger supramolecular systems with attractive molecular architecture, such as cavitands [ 14 ], carcaplexes [ 15 ], dimers [ 16 ], and hexamers, have also been constructed [ 17 ].…”