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Fischer Projections

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Learning to draw Fischer projections of molecules and understanding their relevance plays a crucial role in the visual depiction of organic molecules. A Fischer projection is a two-dimensional projection on a planar surface to simplify the three-dimensional wedge–dash representation of molecules. This is especially helpful in the case of molecules with multiple chiral centers that can be difficult to draw. Here, all the bonds of interest are represented as horizontal or vertical lines.

Chirality

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Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
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¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons

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Folded Propeller Chiral Structures Exclusively Adaptive to Chloroform.

Jianjian Zhao¹, Aiyou Hao¹, Pengyao Xing¹

¹School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China.

|February 17, 2022

Summary

Chiral benzimidazole compounds can be controllably folded using hydrogen bonds. Chloroform uniquely inverts their propeller chirality, demonstrating solvent-mediated stereochemical control in chiral aryl compound synthesis.

Keywords:

adaptiveness chirality circularly polarized luminescence folded structure solvent

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Area of Science:

Organic Chemistry
Supramolecular Chemistry
Materials Science

Background:

Intramolecular folding is key for creating chiral aryl compounds used in chiroptical materials and catalysis.
The influence of solvents on controlling folded chirality, beyond simple polarity, remains unclear.

Purpose of the Study:

To develop a straightforward folding protocol for synthesizing chiral benzimidazole derivatives.
To investigate the role of solvents, particularly chloroform, in modulating the propeller chirality of these compounds.

Main Methods:

A folding strategy utilizing hydrogen bonds to construct a chiral benzimidazole skeleton with diamino acid arms.
Exploration of solvent effects on the folding and chirality of the synthesized compounds.
Utilizing heating and cooling cycles to induce reversible unfolding and folding.

Main Results:

A novel chiral benzimidazole skeleton with propeller chirality was successfully synthesized.
The handedness of the propeller chirality was tunable by the absolute chirality of the amino acid components.
Chloroform (CHCl3) was found to exclusively invert the propeller chirality among 32 tested solvents.
A thermomediated chiroptical switch was achieved through reversible folding/unfolding.

Conclusions:

Solvent participation, not just polarity, can actively alter the chirality and optical properties of small folded molecules.
Chloroform's unique interaction, acting as an invasive linker, rearranges molecular packing to invert chirality.
This work provides a facile method for fabricating adaptive chiral aryl compounds.