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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

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Published on: February 15, 2016

Stereochemical Alignment in Triphospha[3]ferrocenophanes.

Stefan Borucki¹, Zsolt Kelemen¹, Martin Maurer¹

¹Institut für Chemie und CINSaT, Universität Kassel, Heinrich Plett-Straße 40, 34132, Kassel, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|May 31, 2017

Summary

Researchers synthesized novel triphospha[3]ferrocenophanes, observing selective diastereomer formation. Their electronic properties, influenced by stereochemistry, were confirmed by calculations and cyclic voltammetry (CV) measurements.

Keywords:

ab initio calculations ferrocene heteronuclear NMR spectroscopy phosphorus triphosphanes

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Published on: August 12, 2019

Area of Science:

Organometallic Chemistry
Coordination Chemistry
Stereochemistry

Background:

Ferrocenophanes are organometallic compounds with unique structural and electronic properties.
Understanding the stereochemical control in ferrocenophane synthesis is crucial for developing new materials.
The electronic structure of ferrocenophanes, particularly the Highest Occupied Molecular Orbital (HOMO), dictates their reactivity and potential applications.

Purpose of the Study:

To synthesize and characterize a series of triphospha[3]ferrocenophanes with varying substituents.
To investigate the stereoselective formation of diastereomers in these ferrocenophane systems.
To elucidate the relationship between stereochemistry, electronic structure (HOMO localization), and conformation.

Main Methods:

Synthesis of triphospha[3]ferrocenophanes (Fe(C5H4-PtBu)2PX, X=H, F, Cl, Br, I, NEt2, tBu).
Characterization using heteronuclear NMR spectroscopy and X-ray crystallography.
Theoretical calculations to study stereogenic centers and frontier orbital sequences.
Cyclic voltammetry (CV) measurements to probe electronic properties.

Main Results:

Selective formation of one or two diastereomers was observed despite three stereogenic centers.
Theoretical calculations showed that central stereocenter inversion alters the HOMO sequence (iron vs. phosphorus centered).
Cyclic voltammetry results corroborated the theoretical electronic structure predictions.
The all-tert-butyl substituted ferrocenophane exhibited a chiral staggered conformation distinct from its phenyl analogue.

Conclusions:

Stereochemistry plays a critical role in controlling the diastereomeric outcome and electronic properties of triphospha[3]ferrocenophanes.
The observed conformational differences highlight the impact of substituent bulk on solid-state structures.
These findings provide insights into the structure-property relationships of organometallic cage compounds.