Meso-functionalization of calix[4]arene with 1,3,7-triazapyrene in the design of novel fluorophores with the dual target detection of Al³⁺ and Fe³⁺ cations

Abstract

Novel bifunctional fluorophores with the dual target detection of Al3+ and Fe3+ cations were synthesized in yields up to 70% via bridge-functionalization of calix[4]arenes with the 1,3,7-triazapyrene scaffold.

A summary of calixarene-based fluorescent sensors developed during the past five years

“…Additionally, cellular non-toxicity of 11 was evaluated by an MTT assay, permitting its applications to be extended to the biology field. Moseev et al reported mesofunctionalization of calix [4]arene 12 with 1,3,7-triazapyrene for the dual target detection of Al 3+ and Fe 3+ cations 40 (Fig. 6).…”

A Fluorescent Probe for Al3+ Based on Calix[4]arene Containing Salicylaldehyde‐Derived Schiff Base

“…In 2019, the Rao group prepared a calix[4]arene‐coupled cyclic compound by connecting nitrobenzimidazole (NBD) to the lower rim of calix[4]arene for recognizing trivalent metal ions (Cr 3+ , Fe 3+ , Al 3+ ) [8] . Most recently, the Chupakhin group designed a 1,3,7‐triazaperylene calix[4]arene for detecting Al 3+ and Fe 2+ [9] …”

“…[8] Most recently, the Chupakhin group designed a 1,3,7-triazaperylene calix [4]arene for detecting Al 3 + and Fe 2 + . [9] In the past decade, our group has developed a series of upper and lower-rim functionalized calix [4]arenes to achieve various organic catalysis and molecular recognition. [10] Notably, we have found that upper-rim functionalized calix [4]arenes have distinct advantages over the common lower-rim functionalized calixarenes in their ability to fully utilize the calix [4]arene cavity structure and cation ••• π interactions to enhance recognition abilities.…”

Mechanochemically Induced Cross Dehydrogenative Coupling Reactions under Ball Milling

“…The extensive development of transition‐metal‐free CH‐functionalization reactions started only in the decade of 1960–1970 and first review article was published in 1976 [10] . Now transition‐metal‐free C−H functionalization has become an obvious choice for the direct functionalization of (het)arenes, [11–16] including macrocycles [17–20] …”

“…[10] Now transition-metal-free CÀ H functionalization has become an obvious choice for the direct functionalization of (het)arenes, [11][12][13][14][15][16] including macrocycles. [17][18][19][20] The early and pioneering transition-metal-catalyzed CÀ H functionalization/activation reaction in…”