Structural identification of a novel axially chiral binaphthyl fluorene based salen ligand in solution using electronic circular dichroism: a theoretical-experimental analysis

The Journal of Physical Chemistry. a
Carlos DíazFlorencio E Hernández

Abstract

A novel axially chiral binaphthyl fluorene based salen ligand, AFX-155 [2,2'-(1E,1'E)-(R)-1,1'-binaphthyl-2,2'-diylbis(azan-1-yl-1-ylidene)bis(methan-1-yl-1-ylidene)bis(4-((7-(diphenylamino)-9,9-dihexyl-9H-fluoren-2-l)ethynyl)phenol)], with potential applications in homogeneous catalysis, biophotonics, and sensing was synthesized. A full comparative theoretical-experimental analysis of the UV-vis and electronic circular dichroism (ECD) spectra of the 10 primary isomers, comprising stereoisomers and optical isomers, revealed the presence of the unique structure in tetrahydrofuran (THF) solution, the trans-R-intra//trans-R-extra. A proposed route of attack of the (R)-(+)-2,2'-diamino-1,1'-binapthalene onto a salicaldehyde 5-(2-(2-(diphenylamino)-9,9-dihexyl-9H-fluoren-7-yl)ethynyl)-2-hydroxybenzaldehyde followed by a consecutive attack of the resulting species onto another salicaldehyde, both via Burgi:Dunitz trajectory, validates the unambiguous formation of the established isomer. Steric hindrances seem to be the determinant factor that defines the 3D structural conformation of this particular stereoisomer of AFX-155 with triple axial chirality. The determination of every optimal structure and the dominant conformers of AFX-155...Continue Reading

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