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Macrocyclic [2]catenane structures: influence of (aryl) substitution on the self templation of ligands in macrocyclic synthesis
The synthesis of four 2,6-bis(1,2,3-triazol-4-yl)pyridine ( btp ) olefin based ligands 3 , 4 , 11 and 12 is described and their attempted use to form mechanically interlocked molecules using ring closing metatheses (RCM) reactions. The btp ligands were modified in two ways, in 3 and 4 the aryl subst...
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| Published in: | Organic & biomolecular chemistry 2021-12, Vol.19 (46), p.1189-12 |
|---|---|
| Main Authors: | , , , |
| Format: | Article |
| Language: | |
| Online Access: | Get full text |
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| Summary: | The synthesis of four 2,6-bis(1,2,3-triazol-4-yl)pyridine (
btp
) olefin based ligands
3
,
4
,
11
and
12
is described and their attempted use to form mechanically interlocked molecules using ring closing metatheses (RCM) reactions. The
btp
ligands were modified in two ways, in
3
and
4
the aryl substitution pattern was changed from 4
th
position to 3
rd
position and in the case of
11
and
12
, the arms were replaced with aliphatic chains. Our study demonstrates that for all four ligands, the RCM reactions only result in the formation of macrocyclic structures, which in three of the cases, were structurally characterised in both solution (using NMR and HRMS) and in the solid-state using X-ray crystallography. NMR studies were also carried out to investigate if these ligands could preorganise in solution
via
hydrogen bonding interactions. This study provides a handle of how such precursor substitution can be used to direct the formation of macrocycles or mechanically interlocked structures.
The synthesis of four 2,6-bis(1,2,3-triazol-4-yl)pyridine(
btp
) olefin based ligands
3
,
4
,
11
and
12
is described and their formation of macrocyclic products using ring closing metatheses (RCM) reactions rather than mechanically interlocked molecules. |
|---|---|
| ISSN: | 1477-0520 1477-0539 |
| DOI: | 10.1039/d1ob02032c |