engleski

Benzimidazole-1, 2, 3-triazole derivatives and bis-(1, 2, 3-triazolyl-benzimidazolyl)benzenes: synthesis and chemosensing properties

Nitrogen-containing heterocycles are widely investigated structures in the field of biology, medicine and chemical sensors. Benzimidazole and its derivatives are one of the most important building blocks in the design of novel biologically active molecules due to their structural similarity with naturally occuring nucleotides. In addition, combination of π-bridging and electron accepting properties of benzimidazole unit together with its metal-ion chelating ability and pH sensitivity, validated benzimidazole derivatives as promising candidates in fluorescent cellular imaging and metal ion sensing. Introduction of different electron donating and/or electron withdrawing substituents in the benzimidazole core can significantlly affect the optical characteristics of the resulting molecule [1]. Click-derived triazoles play important roles in sensing mechanisms because of their π-conjugated character and coordinating ability. 1, 2, 3-triazole ring can act as a covalent linkage between benzimidazole and corresponding functional group or can directly participate in binding of the target analyte [2]. In this work we present the synthesis of novel benzimidazole-1, 2, 3-triazole conjugates and 1, 3- and 1, 4-bis(1, 2, 3-triazolyl-benzimidazolyl)benzenes as novel donor-π-acceptor systems using click-chemistry approach. The influence of aryl-substituted 1, 2, 3-triazole unit at position 2 of benzimidazole is studied. All compounds are examined as potential chemosensor molecules for pH and/or different metal cations using UV-vis absorption and fluorescence spectroscopy. Detailed spectroscopic titrations in solutions are performed and fluorescence intensity changes are discussed as continuation of our ongoing research [3]. This work was funded by the Croatian Science Foundation (project HRZZ-3386, iNFiNiTE–SENS).

benzimidazole ; 1, 2, 3-triazole ; synthesis, chemosensor

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