Abstract
A synthesis of a series of mono-T8 and difunctionalized double-decker silsesquioxanes bearing substituted triazole ring(s) has been reported within this work. The catalytic protocol for their formation is based on the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) process. Diverse alkynes were in the scope of our interest—i.e., aryl, hetaryl, alkyl, silyl, or germyl—and the latter was shown to be the first example of terminal germane alkyne which is reactive in the applied process’ conditions. From the pallet of 15 compounds, three of them with pyridine-triazole and thiophenyl-triazole moiety attached to T8 or DDSQ core were verified in terms of their coordinating properties towards selected transition metals, i.e., Pd(II), Pt(II), and Rh(I). The studies resulted in the formation of four SQs based coordination compounds that were obtained in high yields up to 93% and their thorough spectroscopic characterization is presented. To our knowledge, this is the first example of the DDSQ-based molecular complex possessing bidentate pyridine-triazole ligand binding two Pd(II) ions.
Highlights
Polyhedral oligomeric silsesquioxanes (SQs) are a large family of compounds that feature diverse structures with Si-O-Si linkages and tetrahedral Si vertices—i.e., random, amorphous, ladder, and cage-like—and the architecture of the latter has attracted considerable scientific interest
There are some examples of CuAAC methodology applied for silsesquioxanes to introduce the triazole moiety(-ies) substituted at 1,4 positions with the SQs core and organic group
We report on the preparation of mono-T8 and difunctionalized double-decker silsesquioxanes with substituted triazole ring(s)
Summary
Polyhedral oligomeric silsesquioxanes (SQs) are a large family of compounds that feature diverse structures with Si-O-Si linkages and tetrahedral Si vertices—i.e., random, amorphous, ladder, and cage-like—and the architecture of the latter has attracted considerable scientific interest. This, in turn, influences the selection of a respective catalytic procedure for this purpose, e.g., hydrosilylation, cross-metathesis, O-silylation, Friedel-Crafts, silylative, Heck, Suzuki, or Sonogashira coupling reactions [2,7,8,9,10,11,12,13,14,15,16,17,18,19,20] Among these methods, the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) may be an alternative but the only route to yield substituted 1,4-triazole ring functionalities regioselectively [21,22,23]. The second part of the paper is focused on the application of selected SQs with hetaryl substituted triazole moieties as potential ligands in complexing reaction with transition metals (Pd, Rh, Pt), resulting in the formation of res3poef c1t5ive SQs-based coordination systems (Figure 1)
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