Publication date: 8th June 2021
Resorcin[4]arene-based multidentate phosphate ligands with superior binding affinity for nanocrystal surfaces
In nanocrystal chemistry the surface of the particles plays an important role in colloidal stability and solubility. Nanocrystals are often a combination of an inorganic core surrounded by a shell of organic ligands. It has been shown previously that phosphonate ligands have a higher binding affinity for nanocrystal surface than carboxylate ligands.
In this work,1 we designed and synthesized superior ligands with binding affinities that exceed the ones of phosphonic acids. We present two multidentate resorcin[4]arene scaffolds with phosphate binding groups. On the first scaffold, the phosphonates are placed directly onto the scaffold. On the second scaffold, the phosphonates and the scaffold are separated by a short alkyl chain, allowing for more flexibility. After an efficient three- or four-step synthesis, we evaluated their binding affinity by solution NMR. We show that these scaffolds bind in a tridentate fashion at low surface coverage. However, at higher coverage, muldidentate ligands are forced to bind with lower denticity, a results we explain with a simple lattice model. Furthermore, the newly synthesized ligands show a superior binding strength when compared to the carboxylic acids as well as mono-dentate phosphonic acids.
In conclusion, we have shown the advantages and limitations of our multidentate ligands. These ligands are superior to other (non-polymeric) ligands present in the literature and provide a basis for further development of a rich field of ligand chemistry.
DVDE acknowledges the NCCR Molecular Systems Engineering, Basel university and the Swiss National Science Foundation for financial support.
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