The methodology of Cu(I)-mediated 1,3-dipolar cycloaddition was first applied in the synthesis of photoactive 1,2,3-triazolylmodified vinylcarboranes of various architectures. As a result, a series of novel boron-enriched cluster compounds bearing a 1,2,3-triazol−vinyl− carborane conjugated system were synthesized in yields up to 92% and in mild reaction conditions. To reveal the "structure−luminescent properties" correlations attributed to the mutual influence of functional building blocks, the preliminary experiments on photophysical studies were carried out. The intramolecular charge transfer, as well as aggregation induced emission enhancement effects observed, could arouse a particular interest in these azaheterocyclic carboranes as challenging functional elements in the design of advanced materials for molecular electronics.
A convenient
transition-metal-free approach, based on nucleophilic
substitution of hydrogen (SN
H), for consecutive regioselective C–H
functionalization of 1,3,7-triazapyrene scaffolds with carboranyllithium
and phenyllithium is reported. The theoretical calculations disclosed
highlight key features in the regioselectivity and mechanism of the
investigated SN
H transformations. The novel 1,3,7-triazapyrene-based ortho-carboranes obtained have large potential in the field of molecular
electronics as organic luminophores, which are characterized by the
aggregation-induced emission and dual-emission effects.
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