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Two- and Three-Tiered Stacked Architectures by Covalent Assembly
Fengfeng Ren1, Kody J Day1, C Scott Hartley2
1Department of Chemistry & Biochemistry, Miami University, Oxford, OH, 45056, USA.
Angewandte Chemie (International Ed. in English)
|June 15, 2016
Summary
Researchers created covalent stacks using discotic cores and reactive arms. The assembly process, while yielding products, revealed challenges in creating rigid, 3D structures, with racemization depending on structural tiers.
Area of Science:
- Supramolecular Chemistry
- Organic Synthesis
- Materials Science
Background:
- Discotic molecules offer a unique platform for self-assembly into columnar structures.
- Controlled covalent assembly is crucial for designing complex, rigid three-dimensional architectures.
- Understanding conformational dynamics in multi-tiered systems is key to predicting material properties.
Purpose of the Study:
- To synthesize two- and three-tiered covalent stacks from simple discotic cores.
- To investigate the challenges and efficiency of thermodynamically controlled assembly for rigid 3D structures.
- To study the relationship between structural tier number and racemization rates.
Main Methods:
- Functionalization of simple discotic cores with reactive arms.
- Covalent assembly via imine formation to create stacked architectures.
- Analysis of assembly products, including misassembled byproducts.
- Determination of racemization rates as a function of structural tiers.
Main Results:
- Successful synthesis of two- and three-tiered covalent stacks in good yields.
- Observation of competing misassembled byproducts, indicating challenges in controlling assembly.
- Demonstration of a strong dependence of racemization rate on the number of tiers in the structures.
- Structural characterization reveals a central arene stack surrounded by a triple helix of arms.
Conclusions:
- The study demonstrates a viable route to multi-tiered covalent stacks, albeit with assembly challenges.
- The findings highlight the cooperative conformational coupling in these multi-tiered structures.
- The racemization rate serves as a sensitive probe for conformational dynamics in complex supramolecular systems.
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