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Chirality at Nitrogen, Phosphorus, and Sulfur

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Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...

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The hemoglobin in the blood, the chlorophyll in green plants, vitamin B-12, and the catalyst used in the manufacture of polyethylene all contain coordination compounds. Ions of the metals, especially the transition metals, are likely to form complexes.
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Hydrolysis of a Ni-Schiff-Base Complex Using Conditions Suitable for Retention of Acid-labile Protecting Groups

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Schiff-base [4]helicene Zn(II) complexes as chiral emitters.

Mariia Savchuk¹, Steven Vertueux¹, Thomas Cauchy¹

¹Univ Angers, CNRS, MOLTECH-Anjou, SFR MATRIX, F-49000 Angers, France. nicolas.zigon@univ-angers.fr narcis.avarvari@univ-angers.fr.

Dalton Transactions (Cambridge, England : 2003)

|July 14, 2021

Summary

Researchers synthesized chiral zinc(II) complexes with [4]helicene moieties for circularly polarized luminescence (CPL) applications. These novel materials exhibit luminescence and optical activity, paving the way for advanced CPL molecular materials.

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Area of Science:

Coordination Chemistry
Materials Science
Photophysics

Background:

Chiral emissive transition metal complexes are crucial for circularly polarized luminescence (CPL) active molecular materials.
The controlled synthesis of enantiopure complexes is essential for developing advanced CPL applications.

Purpose of the Study:

To synthesize enantiopure and racemic Zn(II) complexes incorporating [4]helicene moieties for CPL studies.
To investigate the structural, luminescent, and optical properties of these novel complexes.

Main Methods:

Synthesis of chiral Zn(II) complexes (1, 2, 3) and an achiral analogue (4) using tetradentate salen ligands and [4]helicene units.
Single crystal X-ray diffraction for structural analysis of intermediates and complexes.
Photoluminescence spectroscopy (emission spectra, quantum yield, lifetime) and optical activity measurements (CD, CPL).
Density Functional Theory (DFT) calculations for property comparison.

Main Results:

Successful synthesis of enantiopure Zn(II) complexes (1, 2) and their racemic counterpart (3), along with achiral complex (4).
Structural characterization confirmed the tetradentate O,N,N,O coordination of salen ligands and the presence of [4]helicene moieties.
Complexes 1 and 4 exhibit visible luminescence (around 560 nm) with a quantum yield up to 15% and a luminescence lifetime of 5.5 ns.
Optical activity was assessed and correlated with DFT calculations.

Conclusions:

The synthesized chiral Zn(II) complexes are promising candidates for CPL active molecular materials.
The study demonstrates a viable synthetic route to chiral metal complexes with [4]helicene substituents for CPL applications.
Further investigation into structure-property relationships can optimize CPL performance.