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DOI: 10.1055/a-1389-9498
Main Group Supramolecular Chemistry Led to Surprising New Directions in the Self-Assembly of Organic Macrocycles, Cages, and Cyclophanes
This work was supported by the US National Science Foundation (NSF) (Grant nos. CHE-1609926 and CHE-2003928), and the NSF Graduate Research Fellowship Program (Grant No. 1309047) (to T.A.S.). We additionally thank the NSF for support in the form of an instrumentation grant (Grant No. CHE-1625529). This account is also based upon work supported by the Bradshaw and Holzapfel Research Professorship in Transformational Science and Mathematics to D.W.J.
Abstract
Cyclophanes are an admirable class of macrocyclic and cage compounds that often display unusual properties due to their high strain and unusual conformations. However, the exploration of new, complex cyclophanes has been encumbered by syntheses that can be low yielding, require harsh reaction conditions, and arduous purification steps. Herein, we discuss our work using metalloid-directed self-assembly and dynamic covalent chemistry to form cryptands. These were then subjected to mild conditions to produce discrete disulfide, thioether and hydrocarbon macrocycles in high yields. ‘Design of Experiments’ was then used to selectively synthesize targeted macrocycles from complex mixtures.
1 Introduction
2 Cryptands to Cyclophanes
3 Functionalizable Macrocycles
4 ‘Design of Experiments’ Targeted Synthesis
5 Conclusions and Outlook
Key words
supramolecular chemistry - cyclophanes - design of experiments - dynamic covalent chemistry - self-assembly - macrocyclesPublication History
Received: 15 January 2021
Accepted after revision: 12 February 2021
Accepted Manuscript online:
12 February 2021
Article published online:
01 March 2021
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