Tetrathiafulvalene-[2.2]paracyclophanes: Synthesis, crystal structures, and chiroptical properties

Cécile Mézière; Magali Allain; Cristina Oliveras-Gonzalez; Thomas Cauchy; Nicolas Vanthuyne; Laura G Sarbu; Lucian M Birsa; Flavia Pop; Narcis Avarvari

doi:10.1002/chir.22831

Tetrathiafulvalene-[2.2]paracyclophanes: Synthesis, crystal structures, and chiroptical properties

Chirality. 2018 May;30(5):568-575. doi: 10.1002/chir.22831. Epub 2018 Feb 9.

Authors

Cécile Mézière¹, Magali Allain¹, Cristina Oliveras-Gonzalez¹, Thomas Cauchy¹, Nicolas Vanthuyne², Laura G Sarbu³, Lucian M Birsa³, Flavia Pop¹, Narcis Avarvari¹

Affiliations

¹ Laboratoire MOLTECH-Anjou, UMR 6200, Université d'Angers, Angers, France.
² Aix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, France.
³ Department of Chemistry, "Al. I. Cuza" University of Iasi, Iasi, Romania.

PMID: 29424942
DOI: 10.1002/chir.22831

Abstract

Two racemic tetrathiafulvalene-[2.2]paracyclophane electron donors EDT-TTF-[2.2]paracyclophane 1 and (COOMe)₂ -TTF-[2.2]paracyclophane 2 have been synthesized via the phosphite mediated cross coupling strategy. Chiral HPLC allowed the optical resolution of the (R_P ) and (S_P ) enantiomers for both compounds. Solid-state structures of (R_P )-1 and (rac)-2 have been determined by single crystal X-ray analysis. Intermolecular π-π and S•••S interactions are disclosed in the packing. Single crystal X-ray analysis of (R_P )-1 combined with experimental and theoretical circular dichroism spectra allowed the assignment of the absolute configuration of the enantiomers of 1 and 2.

Keywords: [2.2]paracyclophane; chiral donors; circular dichroism; crystalline structures; enantiomer resolution; tetrathiafulvalene.

Publication types

Research Support, Non-U.S. Gov't