AI Article Synopsis
- The study presents a method to manipulate axial chirality in perylene diimide-based twistacenes using chiral substituents on the imide position.
- It demonstrates that these substituents influence the helicity of flexible [4]helicene subunits through various analytical techniques, indicating the effectiveness of the remote chirality.
- Additionally, both the type of chiral substituent and the solvent significantly affect the strength and direction of circular dichroism (CD) signals, with DFT calculations highlighting steric interactions as a key factor in inducing preferred helicity.
Article Abstract
We report a reliable way to manipulate the dynamic, axial chirality in perylene diimide (PDI)-based twistacenes. Specifically, we reveal how chiral substituents on the imide position induce the helicity in a series of PDI-based twistacenes. We demonstrate that this remote chirality is able to control the helicity of flexible [4]helicene subunits by UV-vis, CD spectroscopy, X-ray crystallography, and TDDFT calculations. Furthermore, we have discovered that both the chiral substituent and the solvent each has a strong impact on the sign and intensity of the CD signals, highlighting the control of the dynamic helicity in this flexible system. DFT calculations suggest that the steric interaction of the chiral substituents is the important factor in how well a particular group is at inducing a preferred helicity.
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| http://dx.doi.org/10.1021/jacs.2c08323 | DOI Listing |
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