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Switching of inherent chirality driven by self-assembly
Hanna Jędrzejewska1, Marcin Kwit, Agnieszka Szumna
1Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland. agnieszka.szumna@icho.edu.pl.
Chemical Communications (Cambridge, England)
|August 4, 2015
Summary
Chirality in iminoresorcin[4]arenes can be dynamically controlled. Non-covalent interactions with achiral molecules switch this dynamic chirality, confirmed by electronic circular dichroism (ECD) and computational analysis.
Area of Science:
- Supramolecular Chemistry
- Organic Chemistry
- Spectroscopy
Background:
- Imino-based macrocycles, such as iminoresorcin[4]arenes, exhibit complex dynamic behaviors.
- Chirality in molecular systems is crucial for various applications, including asymmetric synthesis and molecular recognition.
- Keto-enol tautomerization is a fundamental process influencing molecular structure and properties.
Purpose of the Study:
- To investigate the dynamic chirality of iminoresorcin[4]arenes.
- To explore the influence of non-covalent interactions on this dynamic chirality.
- To demonstrate the switchable nature of chirality in these systems.
Main Methods:
- Synthesis and characterization of iminoresorcin[4]arenes.
- Experimental electronic circular dichroism (ECD) spectroscopy.
- Theoretical calculations using time-dependent density functional theory (TD-DFT).
Main Results:
- The dynamic chirality of iminoresorcin[4]arenes arises from regioselective and diastereoselective keto-enol tautomerization.
- This dynamic chirality was successfully switched upon interaction with achiral molecules.
- Experimental ECD spectra correlated well with TD-DFT calculations, confirming the observed phenomena.
Conclusions:
- Dynamic chirality in iminoresorcin[4]arenes can be modulated through external stimuli.
- Non-covalent interactions provide an effective strategy for controlling molecular chirality.
- This work offers insights into the design of switchable chiral systems.
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