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Structure of Conjugated Dienes

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Functionalized Hydrocarbon Belts: Synthesis, Structure and Properties.

Yi Peng¹, Shuo Tong¹, Yang Zhang¹

¹MOE Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology, Department of Chemistry, Tsinghua University, Beijing, 100084, China.

Angewandte Chemie (International Ed. in English)

|April 23, 2023

Summary

This summary is machine-generated.

Researchers synthesized novel zigzag hydrocarbon belts containing eight-membered rings. These belts show promise as selective cesium ion hosts and emit circularly polarized luminescence (CPL).

Keywords:

Cesium Circularly Polarized Luminescence Hydrocarbon Belt Resorcin[4]Arene Zigzag

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Area of Science:

Organic Chemistry
Supramolecular Chemistry
Materials Science

Background:

Hydrocarbon belts are of significant interest due to their unique structures and properties.
Synthesis of belt molecules with non-hexagonal rings remains challenging.

Purpose of the Study:

To report the construction of novel zigzag-type hydrocarbon belts containing functionalized eight-membered rings.
To explore the host-guest properties and chiroptical behavior of these new belt molecules.

Main Methods:

Utilized fourfold intramolecular acylation reactions of resorcin[4]arene-derived intermediates.
Performed stereoselective ketone reduction and nucleophilic addition reactions.
Investigated complexation with cesium ions and measured binding constants.
Analyzed circularly polarized luminescence (CPL) of enantiopure belts.

Main Results:

Successfully synthesized C4-symmetric tetrabenzobelt[4]arene[4]cyclooctatrienones with functionalized eight-membered rings.
Developed tetrahydroxylated belts and their methyl ethers capable of forming selective complexes with cesium ions.
Achieved high binding constants for cesium ion complexation, up to (1.71±0.33)×10^11 M^-2.
Demonstrated that enantiopure belts can emit CPL with |g_lum| around 0.01.

Conclusions:

Introduced unprecedented zigzag hydrocarbon belts featuring non-hexagonal rings.
Established the utility of these belts as potent and selective hosts for cesium ions.
Showcased the potential of these chiral belts in chiroptical applications through CPL emission.