Extended enantiopure ortho -phenylene ethylene (o -OPE)-based helical systems as scaffolds for supramolecular architectures: A study of chiroptical response and its connection to the CISS effect

Ana M. Ortuño, Pablo Reiné, Sandra Resa, Luis Álvarez De Cienfuegos, Victor Blanco, José Manuel Paredes, Antonio J. Mota, Giuseppe Mazzeo, Sergio Abbate, Jesus M. Ugalde, Vladimiro Mujica, Giovanna Longhi, Delia Miguel, Juan Manuel Cuerva

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

A novel synthetic strategy based on a bifunctional stapled chiral nucleus from which segments of different lengths can be added to both ends of o-phenylene ethynylenes (o-OPEs) has been developed to obtain a new type of foldamer and a novel chiral Pd2L2 metallacycle. For the first time, an enantiopure fully conjugated helical foldamer having 14 phenyl rings and 13 alkynes is reported. The folded structure has four complete loops and is able to host three Ag(i) cations in their cavity with high binding constants. The complete photophysical and chiroptical (ECD, CPL and VCD) characterization of these foldamers has shown that these molecules show intense chiroptical responses with dissymmetry ratios in the range of 10-2. Theoretical modeling of these systems reveals the origin of these remarkable responses and points out a potential connection with the chiral induced spin selectivity (CISS) effect. The magnetic dipole moment is proposed as a key physical variable connecting the chiroptical properties and CISS-based spin filtering properties observed in chiral compounds.

Original languageEnglish (US)
Pages (from-to)5071-5086
Number of pages16
JournalOrganic Chemistry Frontiers
Volume8
Issue number18
DOIs
StatePublished - Sep 21 2021

ASJC Scopus subject areas

  • Organic Chemistry

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