Triazolyl Conjugated (Oligo)Phenothiazines Building Blocks for Hybrid Materials-Synthesis and Electronic Properties.

Hilla Khelwati,Zhou Zhou,Adam W Franz,Werner R Thiel,Thomas J J Müller

doi:10.3390/molecules26102950

Hilla Khelwati, Zhou Zhou + Show 3 more

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https://doi.org/10.3390/molecules26102950

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Abstract

The Cu-catalyzed alkyne-azide 1,3-dipolar cycloaddition variant provides a highly efficient entry to conjugated triazolyl-substituted (oligo)phenothiazine organosilicon derivatives with luminescence and reversible redox characteristics. Furthermore, by in-situ co-condensation synthesis several representative mesoporous MCM-41 type silica hybrid materials with embedded (oligo)phenothiazines are prepared and characterized with respect to their structural and electronic properties. The hybrid materials also can be oxidized to covalently bound embedded radical cations, which are identified by their UV/Vis absorption signature and EPR signals.

Highlights

Blocks for Hybrid Materials—The mechanistic details of 1,3-dipolar cycloaddition were elucidated by Huisgen and his group almost six decades ago [1]
The precursor materials are all intensively luminescent by triazole substitution and reversible redox systems according to cyclic voltammetry
These favorable electronic properties can be directly included in the mesoporous hybrid materials as well

Summary

Introduction

The mechanistic details of 1,3-dipolar cycloaddition were elucidated by Huisgen and his group almost six decades ago [1]. Ever since, it has become a versatile reaction for the formation of five-membered heterocycles, even in complex natural pro-duct syntheses [2]. It has become a versatile reaction for the formation of five-membered heterocycles, even in complex natural pro-duct syntheses [2] It took almost 40 years for 1,3-dipolar cycloadditions, among other highly atom economical (cyclo)additions, to lead to the formulation of the “click chemistry” concept, coined by Sharpless and coauthors [3]. Mechanistic elucidation [8], catalyst design [9], and implementation into multicomponent methodologies [10] mark basic expansions of CuAAC over the years

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Conclusion