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Optically Active Cyclic Oligomers Based on Planar Chiral [2.2]Paracyclophane.

Kentaro Tanaka¹, Ryo Inoue¹, Yasuhiro Morisaki¹

¹Department of Applied Chemistry for Environment, School of Biological and Environmental Sciences, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo, 669-1337, Japan.

Chemistry, an Asian Journal

|November 30, 2021

Summary

Optically active cyclic molecules were synthesized using chiral building blocks. The cyclic trimers and tetramers showed strong circularly polarized luminescence (CPL), indicating potential for advanced optical applications.

Keywords:

[2.2]paracyclophane circular dichroism circularly polarized luminescence cyclic oligomer planar chirality

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Area of Science:

Supramolecular Chemistry
Organic Chemistry
Materials Science

Background:

Chiral molecules are crucial for various applications, including asymmetric synthesis and optical devices.
Paracyclophanes offer a unique scaffold for constructing complex chiral architectures.
Understanding structure-property relationships in chiral systems is essential for designing new functional materials.

Purpose of the Study:

To synthesize optically active cyclic oligomers of p-arylene-ethynylenes.
To investigate the chiroptical properties, including Cotton effects and circularly polarized luminescence (CPL).
To explore the potential of these molecules in chiroptical applications.

Main Methods:

Synthesis of enantiopure 4,7,12,15-tetrasubstituted [2.2]paracyclophane as a chiral building block.
Preparation of cyclic dimer, trimer, and tetramer structures.
Spectroscopic analysis including UV-Vis absorption and emission spectroscopy.
Circular dichroism (CD) and CPL measurements.
Time-dependent density functional theory (TD-DFT) calculations.

Main Results:

Successful synthesis of optically active cyclic p-arylene-ethynylene oligomers.
Observation of distinct Cotton effects in absorption spectra with mirror-image relationships for enantiomers.
CPL emission observed for cyclic trimers and tetramers, with signs correlating to Cotton effects.
Molecular orbitals localized in p-arylene-ethynylene units in excited states.
High dissymmetry factors (around 10^-3) for CPL in trimers and tetramers.
TD-DFT calculations accurately reproduced the observed optical and chiroptical properties.

Conclusions:

Enantiopure paracyclophanes serve as effective chiral building blocks for optically active cyclic oligomers.
Cyclic trimers and tetramers exhibit intense and efficient CPL, suggesting their utility in chiral optoelectronics.
The study provides fundamental insights into the relationship between molecular structure and chiroptical behavior in these systems.