Multi-chiro-informative System Created by a Porphyrin-functionalized Chiral Molecular Assembly

Abstract

We introduce multi-chiroptically active organic systems that exhibit circular dichroism, fluorescence and circularly polarized luminescence through chiral molecular orientation of a non-chiral porphyrin moiety. The spectra of these unique systems are distinctly sensitive to external conditions, including an enantiomeric factor.

Chiroptical Polymer Functionalized by Chiral Nanofibrillar Network

“…In cyclohexane, a very large CD intensity is observed near the absorption band of porphyrin, but since there is no asymmetric carbon or chirality at the porphyrin site, the expression of the large CD signal is attributed to chiral orientation among the porphyrin moieties in cyclohexane gel. The addition of an imidazole derivative to this G-Por gel remarkably changes the CD pattern, but such a change does not occur with the addition of pyridine at the same concentration, [87] which is attributed to the different coordination abilities of the guest molecules.…”

“…Examples of CD responsibilities in G-Py + (a), [4,81] G-por (b), [87] and G-T P y (c) [67] assemblies by external factors. [4,81,87]…”

Enantioselective Self-Assembled Nanofibrillar Network with Glutamide-Based Organogelator

“…The first examples of chiral separation using organogels were reported as enantioselective transport phenomena of amino acid derivatives from gels to aqueous phases [ 10 ]. Since then, most of the remarkable enantioselectivities obtained using chiral organogels have been realized by the introduction of special supramolecular or multi-functional groups, such as a porphyrin [ 11 , 12 ], a pyridylpyrazole [ 13 ], and a quinolinol [ 14 ] into a molecule. In this study, we aimed to induce enantioselectivity through amplification of chirality using simple functional groups in a manner that does not rely on a supramolecular functional group.…”