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Synthesis and properties of bis-porphyrin molecular tweezers: effects of spacer flexibility on binding and supramolecular chirogenesis

Synthesis and properties of bis-porphyrin molecular tweezers: effects of spacer flexibility on binding and supramolecular chirogenesis
Synthesis and properties of bis-porphyrin molecular tweezers: effects of spacer flexibility on binding and supramolecular chirogenesis
Ditopic binding of various dinitrogen compounds to three bisporphyrin molecular tweezers with spacers of varying conformational rigidity, incorporating the planar enediyne (1), the helical stiff stilbene (2), or the semi-rigid glycoluril motif fused to the porphyrins (3), are compared. Binding constants Ka = 104–106 M?1 reveal subtle differences between these tweezers, that are discussed in terms of porphyrin dislocation modes. Exciton coupled circular dichroism (ECCD) of complexes with chiral dinitrogen guests provides experimental evidence for the conformational properties of the tweezers. The results are further supported and rationalized by conformational analysis.
bisporphyrin tweezers, metalloporphyrins, porphyrinoids, host-guest chemistry, supramolecular chemistry, chirogenesis, chirality transfer, exciton coupled circular dichroism, conformational analysisdichroism, conformational analysis
1-24
Blom, Magnus
7d13b39b-c30b-4f0e-916f-98fb89cadbd6
Norrehed, Sara
f3df8490-6239-405c-90b9-b006449d03bb
Andersson, Claes-Henrik
350659b3-b4c7-4691-870d-ff23cb7448f0
Huang, Hao
4f499349-1420-4d62-9a03-29e7de60e00b
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Bergquist, Jonas
2532f2e4-2298-407b-8dcb-849d8cf8c2aa
Grennberg, Helena
df1a6f54-37f2-4c7b-93cb-11447c50d753
Gogoll, Adolf
1769b3c3-6b75-496a-ac4b-89041c2d5126
Blom, Magnus
7d13b39b-c30b-4f0e-916f-98fb89cadbd6
Norrehed, Sara
f3df8490-6239-405c-90b9-b006449d03bb
Andersson, Claes-Henrik
350659b3-b4c7-4691-870d-ff23cb7448f0
Huang, Hao
4f499349-1420-4d62-9a03-29e7de60e00b
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Bergquist, Jonas
2532f2e4-2298-407b-8dcb-849d8cf8c2aa
Grennberg, Helena
df1a6f54-37f2-4c7b-93cb-11447c50d753
Gogoll, Adolf
1769b3c3-6b75-496a-ac4b-89041c2d5126

Blom, Magnus, Norrehed, Sara, Andersson, Claes-Henrik, Huang, Hao, Light, Mark, Bergquist, Jonas, Grennberg, Helena and Gogoll, Adolf (2015) Synthesis and properties of bis-porphyrin molecular tweezers: effects of spacer flexibility on binding and supramolecular chirogenesis. Molecules, 21 (1), 1-24. (doi:10.3390/molecules21010016).

Record type: Article

Abstract

Ditopic binding of various dinitrogen compounds to three bisporphyrin molecular tweezers with spacers of varying conformational rigidity, incorporating the planar enediyne (1), the helical stiff stilbene (2), or the semi-rigid glycoluril motif fused to the porphyrins (3), are compared. Binding constants Ka = 104–106 M?1 reveal subtle differences between these tweezers, that are discussed in terms of porphyrin dislocation modes. Exciton coupled circular dichroism (ECCD) of complexes with chiral dinitrogen guests provides experimental evidence for the conformational properties of the tweezers. The results are further supported and rationalized by conformational analysis.

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More information

Accepted/In Press date: 7 December 2015
Published date: 23 December 2015
Keywords: bisporphyrin tweezers, metalloporphyrins, porphyrinoids, host-guest chemistry, supramolecular chemistry, chirogenesis, chirality transfer, exciton coupled circular dichroism, conformational analysisdichroism, conformational analysis
Organisations: Chemistry, Faculty of Natural and Environmental Sciences

Identifiers

Local EPrints ID: 392637
URI: https://eprints.soton.ac.uk/id/eprint/392637
PURE UUID: a73a716c-22dc-477f-9b94-b8d8e6728c20
ORCID for Mark Light: ORCID iD orcid.org/0000-0002-0585-0843

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Date deposited: 15 Apr 2016 08:00
Last modified: 15 Aug 2019 00:50

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