CuAAC click reactions for the design of multifunctional luminescent ruthenium complexes

Abstract

CuAAC (Cu(i) catalyzed azide-alkyne cycloaddition) click chemistry has emerged as a versatile tool in the development of photoactive ruthenium complexes with multilateral potential applicability. In this contribution we discuss possible synthetic approaches towards CuAAC reactions with ruthenium(ii) polypyridine complexes and their differences with respect to possible applications. We focus on two main application possibilities of the click-coupled ruthenium assemblies. New results within the development of ruthenium based photosensitizers for the field of renewable energy supply, i.e. DSSCs (dye-sensitized solar cells) and artificial photocatalysis for the production of hydrogen, or for anticancer photodynamic therapeutic applications are reviewed.

A novel process for copper protection in the simulated industrial cooling water based on click synthesis and self‐assembling method

“…Cu(I)‐catalyzed azide‐alkyne 1,3‐dipolar cycloaddition (CuAAC) reaction is a classical click chemistry reaction, it generates 1,4‐disubstituted 1,2,3‐triazoles between azides and terminal alkynes. Click synthesis reaction is featured as low reagent consumption, simple reaction condition, high yield, and exquisite selectivity, having been used in many fields such as bioscience, polymer preparation, membrane engineering, and material protection …”

One Scaffold, Many Possibilities – Copper(I)‐Catalyzed Azide–Alkyne Cycloadditions, Strain‐Promoted Azide–Alkyne Cycloadditions, and Maleimide–Thiol Coupling of Ruthenium(II) Polypyridyl Complexes

“…Biological applications are particularly limited by the choice of linkage given that bioorthogonal conditions have to be applied. Click chemistry approaches such as the copper(I)‐catalyzed azide–alkyne cycloaddition (CuAAC), strain‐promoted azide–alkyne cycloaddition (SPAAC), and maleimide–thiol coupling represent advantageous strategies to link sensitive (bio)molecules with functional units, for example, photosensitizers or other imaging agents, and the control of the coupling is dependent on the corresponding functionalities. For photodynamic therapy (PDT), one feasible approach is to couple selectivity‐mediating biomolecules to photosensitizers such as Ru II polypyridyl complexes .…”

“…Moreover, the choice of azide–alkyne cycloadditions provides the advantage that the reacting groups are not abundant in the body and, therefore, guarantees high selectivity and control. CuAAC is useful for the development of new drug systems as well as many other applications , . Even though CuAAC is a chemically very selective coupling method, the employment of cell‐toxic copper ions for CuAAC reactions requires extensive purification and limits the exploitation of the CuAAC for live cell studies and for reactions that must avoid possible copper‐ion coordination.…”

“…CuAAC is useful for the development of new drug systems as well as many other applications. [1,8] Even though CuAAC is a chemically very selective coupling method, the employment of cell-toxic copper ions for CuAAC reactions requires extensive purification and limits the exploitation of the CuAAC for live cell studies and for reactions that must avoid possible copper-ion coordination. The use of to one easy-to-synthesize scaffold, which has proven to be convenient for the application of metal chromophores.…”

Novos complexos polipiridínicos de rutênio: explorando a aplicação em DSSC\'s e as propriedades fotoquímicas

“…ISC=cruzamente intersistema; n.r.= desativação não radioativa. Adaptado de [106] A desativação do estado excitado pode ocorrer por processos radiativos como é o caso da fluorescência e da fosforescência. A fluorescência ocorre a partir do estado excitado que possui mesma multiplicidade de spin que o estado fundamental enquanto que a fosforescência ocorre a partir de um estado excitado de multiplicidade diferente daquela do estado fundamental [104].…”