1,3,7-Triazapyrene-Based ortho-Carborane Fluorophores: Convenient Synthesis, Theoretical Studies, and Aggregation-Induced Emission Properties

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...

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Bibliographic Details
Published in:Organometallics 2021-08, Vol.40 (16), p.2792-2807
Main Authors: Smyshliaeva, Lidia A, Varaksin, Mikhail V, Fomina, Ekaterina I, Medvedeva, Margarita V, Svalova, Tatiana S, Kozitsina, Alisa N, Demidov, Oleg P, Borovlev, Ivan V, Mensch, Carl, Mampuys, Pieter, Maes, Bert U. W, Charushin, Valery N, Chupakhin, Oleg N
Format: Article
Language:English
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Summary: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.
ISSN:0276-7333
1520-6041
DOI:10.1021/acs.organomet.1c00234