Atropisomeric Chiral Probes to Study the Supramolecular Organization in Porphyrin Self-Assemblies

作者：Chappaz Gillot Cyril; Canard Gabriel^*; Andreoli Federico; Vanthuyne Nicolas; Giorgi Michel; Naubron Jean Valere; Monnier Valerie; Rosas Roselyne; Roussel Christian; Balaban Teodor Silviu

来源：European Journal of Organic Chemistry, 2012, (33): 6526-6536.

DOI：10.1002/ejoc.201200985

• Porphyrinoids
• Self-assembly
• Chirality
• Circular dichroism
• Aggregation

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 metalligand 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.

• 出版日期2012-11