Issue 28, 2024

Host–guest chemistry of tridentate Lewis acids based on tribenzotriquinacene

Abstract

Flexible poly-Lewis acids (PLA) based on the tribenzotriquinacene (TBTQ) scaffold have been synthesised. Hydrosilylation of 4b,8b,12b-triallyltribenzotriquinacene and subsequent exchange of the chlorine substituents with weaker coordinating triflate groups afforded a novel triple silyl-functionalised PLA. By regioselective hydroboration of triallyl–TBTQ with various organoboranes, PLAs with different Lewis acidities were obtained. The synthesised PLAs were combined with neutral bases in host–guest experiments. DOSY NMR spectroscopy was performed to elucidate the complexation process in solution. These experiments revealed a highly dynamic interaction between the boron-functionalised PLA and triazine. However, the addition of one equivalent of tris(dimethylphosphino(methyl))phenylsilane led to the formation of a 1 : 1 adduct, which was confirmed by diffusion experiments.

Graphical abstract: Host–guest chemistry of tridentate Lewis acids based on tribenzotriquinacene

Supplementary files

Article information

Article type
Paper
Submitted
28 May 2024
Accepted
28 Jun 2024
First published
01 Jul 2024
This article is Open Access
Creative Commons BY license

Dalton Trans., 2024,53, 11970-11980

Host–guest chemistry of tridentate Lewis acids based on tribenzotriquinacene

M. Franke, T. Ens, A. Mix, B. Neumann, H. Stammler and N. W. Mitzel, Dalton Trans., 2024, 53, 11970 DOI: 10.1039/D4DT01558D

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