Chirality Transfer, Memory and Sensing Activated by a Supramolecular Chiral Auxiliary Approach in Nanostructured, Tautomerically Prochiral Triptycene-Fused Benzimidazoles

Year: 2026

Authors: Preda G., Mobili R., Longhi G., Meli M., Colombo G., Amendola V., Pasini D.

Autors Affiliation: Univ Pavia, Dept Chem, I-27100 Pavia, Italy; Univ Pavia, INSTM Res Unit, I-27100 Pavia, Italy; Univ Brescia, Dipartimento Med Mol & Traslazionale, I-25123 Brescia, Italy; CSMT, Res Unit Brescia, INO CNR, I-25123 Brescia, Italy; Ist Sci & Tecnol Chim Giulio Natta SCITEC CNR, I-20131 Milan, Italy.

Abstract: We report the synthesis and characterization of stimuli responsive, adaptive organic chiral nanoparticles assembled using a stereochemically fluid, triptycene-fused benzimidazole, which is chiroptically activated by the noncovalent interaction with enantiopure tartaric acid, acting as a supramolecular chiral auxiliary. Under appropriate experimental conditions, the formation of chiral supramolecular aggregates exhibits remarkable chiroptical properties (electronic circular dichroism, ECD, and circularly polarized luminescence, CPL) with the possibility of addressing their controlled manipulation, reversion between the states, and chirality memory properties. Furthermore, the nanostructured system is capable of selective sensing of the Cu2+ ion through the modulation of its chiroptical properties. In this manner, we provide an unprecedented way to introduce chirality onto the triptycene skeleton to assemble well-defined chiral nanoparticles with dimensions of several hundred nanometers and to reversibly store chiral information and activate chiroptical sensing properties.

Journal/Review: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

More Information: We thank Sergio Abbate (University of Brescia) for the useful discussion, Giuseppe Mazzeo (University of Brescia) for help with the CPL analysis, and Prof. Yuri Antonio Diaz Fernandez (University of Pavia) for help with DLS measurements. We acknowledge the CINECA award under the ISCRA initiative for the availability of high-performance computing resources and support.
KeyWords: Derivatives; Films
DOI: 10.1021/jacs.6c03689