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Atropisomeric Chiral Probes to Study the Supramolecular Organization in Porphyrin Self‐Assemblies
Author(s) -
ChappazGillot Cyril,
Canard Gabriel,
Andreoli Federico,
Vanthuyne Nicolas,
Giorgi Michel,
Naubron JeanValère,
Monnier Valérie,
Rosas Roselyne,
Roussel Christian,
Balaban Teodor Silviu
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200985
Subject(s) - chemistry , atropisomer , porphyrin , supramolecular chemistry , circular dichroism , self assembly , crystallography , metal , ligand (biochemistry) , photochemistry , stereochemistry , organic chemistry , crystal structure , biochemistry , receptor
Abstract A noncatalysed nucleophilic aromatic substitution was used to prepare the (bacterio)chlorophyll mimics 2 ‐Zn, 3 ‐Zn, 4 ‐Zn and 5 ‐Zn. The localisation of the two recognition groups on the same side of the porphyrin macrocycles in 2 ‐Zn, 4 ‐Zn and 5 ‐Zn produces, through metal–ligand interactions, oligomers that display both H‐ and J‐type aggregates. These supramolecular architectures were confirmed by the introduction of optically pure atropisomers in 5 ‐Zn, which produces chiral aggregates. The UV/Vis and electronic circular dichroism spectra of all aggregates are used to propose an excitonic splitting mode that would correspond to this dual type of chromophoric self‐assembly.