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Issue 23, 2020
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One-pot synthesis of porphyrin-based [5]rotaxanes

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A one-pot reaction is used to make a series of [5]rotaxanes. The protocol involves simultaneous threading-followed-by-stoppering to trap a macrocycle (dibenzo[24]crown-8, DB24C8) on an axle to form a mechanically interlocked molecule (MIM) – in this case a rotaxane – and the condensation of an aldehyde with a pyrrole to form a porphyrin precursor. For each [5]rotaxane, a different combination of recognition site and stoppering group was used; the protonation state of the [5]rotaxane can be used to generate different co-conformational states for each [5]rotaxane making these systems potential multi-state switches for further study in solution or the solid-state.

Graphical abstract: One-pot synthesis of porphyrin-based [5]rotaxanes

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Supplementary files

Article information

30 Apr 2020
26 May 2020
First published
27 May 2020

Org. Biomol. Chem., 2020,18, 4395-4400
Article type

One-pot synthesis of porphyrin-based [5]rotaxanes

P. Martinez-Bulit, B. H. Wilson and S. J. Loeb, Org. Biomol. Chem., 2020, 18, 4395
DOI: 10.1039/D0OB00906G

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