Abstract
Three bis-p-phenylene-34-crown-10 (BPP34C10) derivatives bearing ester groups on one or both of their two aromatic rings have been synthesized. These ester-substituted macrocyclic polyethers bind the paraquat dication in solution more strongly than BPP34C10. In contrast, however, acyclic analogs of these macrocyclic polyethers form much weaker complexes with cyclobis(paraquat-p-phenylene) (CBPQT4+). Likewise, catenane formation is diminished, in parallel with the number and disposition of the ester substituents on the hydroquinone rings of the macrocyclic polyethers. These observations suggest that complex and catenane formation are controlled by opposing recognition features, according to whether the ester-substituted hydroquinone rings assume either a guest or host role in 1:1 complexes with bipyridinium-based species, or lie inside or alongside the CBPQT4+ component in the[2]catenanes. Steric and electronic factors associated with the ester substituents probably account for the opposing trends in the inter-component recognition behavior.
| Original language | English |
|---|---|
| Pages (from-to) | 3799-3808 |
| Number of pages | 10 |
| Journal | Tetrahedron |
| Volume | 57 |
| Issue number | 17 |
| DOIs | |
| Publication status | Published - 2001 Apr 23 |
| Externally published | Yes |
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Keywords
- Aromatic interactions
- Catenanes
- Crystal structures
- Molecular recognition
- Template-directed synthesis
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
The balance between electronic and steric effects in the template-directed syntheses of [2]catenanes. / Pérez-Alvarez, Marta; Raymo, Françisco M.; Rowan, Stuart J.; Schiraldi, David; Stoddart, J. Fraser; Wang, Zhen He; White, Andrew J P; Williams, David J.
In: Tetrahedron, Vol. 57, No. 17, 23.04.2001, p. 3799-3808.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - The balance between electronic and steric effects in the template-directed syntheses of [2]catenanes
AU - Pérez-Alvarez, Marta
AU - Raymo, Françisco M.
AU - Rowan, Stuart J.
AU - Schiraldi, David
AU - Stoddart, J. Fraser
AU - Wang, Zhen He
AU - White, Andrew J P
AU - Williams, David J.
PY - 2001/4/23
Y1 - 2001/4/23
N2 - Three bis-p-phenylene-34-crown-10 (BPP34C10) derivatives bearing ester groups on one or both of their two aromatic rings have been synthesized. These ester-substituted macrocyclic polyethers bind the paraquat dication in solution more strongly than BPP34C10. In contrast, however, acyclic analogs of these macrocyclic polyethers form much weaker complexes with cyclobis(paraquat-p-phenylene) (CBPQT4+). Likewise, catenane formation is diminished, in parallel with the number and disposition of the ester substituents on the hydroquinone rings of the macrocyclic polyethers. These observations suggest that complex and catenane formation are controlled by opposing recognition features, according to whether the ester-substituted hydroquinone rings assume either a guest or host role in 1:1 complexes with bipyridinium-based species, or lie inside or alongside the CBPQT4+ component in the[2]catenanes. Steric and electronic factors associated with the ester substituents probably account for the opposing trends in the inter-component recognition behavior.
AB - Three bis-p-phenylene-34-crown-10 (BPP34C10) derivatives bearing ester groups on one or both of their two aromatic rings have been synthesized. These ester-substituted macrocyclic polyethers bind the paraquat dication in solution more strongly than BPP34C10. In contrast, however, acyclic analogs of these macrocyclic polyethers form much weaker complexes with cyclobis(paraquat-p-phenylene) (CBPQT4+). Likewise, catenane formation is diminished, in parallel with the number and disposition of the ester substituents on the hydroquinone rings of the macrocyclic polyethers. These observations suggest that complex and catenane formation are controlled by opposing recognition features, according to whether the ester-substituted hydroquinone rings assume either a guest or host role in 1:1 complexes with bipyridinium-based species, or lie inside or alongside the CBPQT4+ component in the[2]catenanes. Steric and electronic factors associated with the ester substituents probably account for the opposing trends in the inter-component recognition behavior.
KW - Aromatic interactions
KW - Catenanes
KW - Crystal structures
KW - Molecular recognition
KW - Template-directed synthesis
UR - http://www.scopus.com/inward/record.url?scp=0035938273&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0035938273&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(01)00257-5
DO - 10.1016/S0040-4020(01)00257-5
M3 - Article
AN - SCOPUS:0035938273
VL - 57
SP - 3799
EP - 3808
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 17
ER -