biostudies-literatureDas PUniversity of FloridaNIH Office of the DirectorNIH HHSNational Science Foundation764-776https://www.ebi.ac.uk/biostudies/studies/S-EPMC12581192biostudies-literatureUnknown13(3)(Chir)optical molecular photoswitches have garnered significant attention for their applications in asymmetric synthesis, supramolecular chemistry, and the materials sciences. The planar chirality and associated photophysical and chiroptical properties of [2.2]paracyclophane ([2.2]pCp) derivatives have been long appreciated. Even so, chiral photoswitches incorporating the [2.2]pCp framework remain largely unexplored. Dicyanorhodanine (RCN), conjugated with oligothiophenes and pyrroles, has been recently shown as a highly competent photoisomerizable scaffold. The current work introduces a novel photoswitch system combining an electron-rich [2.2]pCp moiety with an electron-deficient RCN unit, as a planar chiral "push-pull" architecture. Single crystal X-ray study reveals the <i>Z</i> configuOrganic chemistry frontiers : an international journal of organic chemistry[2.2]Paracyclophane-dicyanorhodanine conjugates as planar chiral molecular photoswitches.PMC12581192CHE-1828064S10 OD030250S10 OD021758S10 OD021758-01A1CHE-2203754S10 OD030250-01A1Dobrzycki LStearns CDCastellano RKDas PGhiviriga Ifalse[2.2]Paracyclophane-dicyanorhodanine conjugates as planar chiral molecular photoswitches.(Chir)optical molecular photoswitches have garnered significant attention for their applications in asymmetric synthesis, supramolecular chemistry, and the materials sciences. The planar chirality and associated photophysical and chiroptical properties of [2.2]paracyclophane ([2.2]pCp) derivatives have been long appreciated. Even so, chiral photoswitches incorporating the [2.2]pCp framework remain largely unexplored. Dicyanorhodanine (RCN), conjugated with oligothiophenes and pyrroles, has been recently shown as a highly competent photoisomerizable scaffold. The current work introduces a novel photoswitch system combining an electron-rich [2.2]pCp moiety with an electron-deficient RCN unit, as a planar chiral "push-pull" architecture. Single crystal X-ray study reveals the <i>Z</i> configu2026-01-01T00:00:00Z2026 Feb2026-07-14T21:03:26.524Z2026-06-25T03:08:05.751ZS-EPMC125811924118967210.1039/d5qo01401h