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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
Template-directed synthesis employing reversible imine bond formation
Cari D Meyer1, C Steven Joiner, J Fraser Stoddart
1Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095, USA.
Chemical Society Reviews
|January 25, 2008
Summary
Dynamic covalent chemistry (DCC) utilizes reversible imine bonds for template-directed synthesis. This approach allows for error correction during molecular assembly, enabling the creation of complex compounds like catenanes and rotaxanes from simple precursors.
Area of Science:
- Organic Chemistry
- Supramolecular Chemistry
- Materials Science
Background:
- Imine bonds form via reversible condensation of amines and aldehydes.
- Template-directed synthesis uses noncovalent interactions for molecular preorganization.
- Dynamic covalent chemistry (DCC) introduces reversibility into covalent bond formation.
Purpose of the Study:
- To review the application of imine bonds as dynamic covalent bonds.
- To explore their role in template-directed synthesis of molecular compounds.
- To highlight the advantages of DCC in creating complex molecular architectures.
Main Methods:
- Utilizing reversible imine bond formation for self-assembly.
- Employing template-directed synthesis strategies.
- Leveraging DCC for error correction and thermodynamic product selection.
Main Results:
- DCC enables 'proofreading' of covalent bonds, favoring thermodynamic products.
- Complex mechanically interlocked compounds (catenanes, rotaxanes, etc.) can be synthesized.
- Molecular self-assembly is optimized through preprogrammed molecular recognition events.
Conclusions:
- The combination of template-directed synthesis and DCC simplifies the construction of complex molecules.
- This paradigm facilitates the creation of mechanically interlocked compounds from simple building blocks.
- DCC offers a powerful strategy for achieving high fidelity in molecular self-assembly.
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