Redox Switches with Chiroptical Signal Expression Based on Binaphthyl Boron Dipyrromethene Conjugates

Abstract

A chiroptical redox switch, the binaphthyl boron dipyrromethene conjugate (R)‐1, is presented. The circular dichroism (CD) couplet of this compound at 501 nm disappears on reduction to the bisradical dianion and is completely restored on reoxidation. The CD effects of (R)‐1 can be explained by quantum‐chemical calculations.

Recent advances towards azobenzene-based light-driven real-time information-transmitting materials

“…Many diverse organic molecules have been investigated for molecular switching applications. Based on these, monomolecular photochromic [2–4], fluorescence [5–6], chirality [7–9], redox [10] and acid–base [11–13] switches have been successfully reported during the past few decades. The interconversion between the different states of the molecular switch can be performed by a great variety of environmental stimuli, which can be classified into three main groups: light energy, electrical energy and chemical energy (pH, solvent, the presence of a determined metal or ligand, etc.).…”

Electroactive Molecules and Supramolecules for Information Processing and Storage

“…The initial CD spectrum is restored completely after reoxidation; thus, the CD signal intensity at 501 nm for R-56 can be switched on and off electrochemically. 59 Dihydro [5]helicenes 57, which contain two electron-donating spiro rings, can undergo reversible CÀC bond breaking to generate dications 57 2 þ . These transformations are accompanied by remarkable absorption spectral changes.…”

An optically transparent thin-layer electrochemical cell for the study of vibrational circular dichroism of chiral redox-active molecules

“…1 Chiral molecules that exhibit distinct chiroptical signatures upon electrochemical generation of radical ions in solution are generally investigated with electronic circular dichroism (ECD) spectroscopy. [2][3][4] The high ECD signal intensities generally observed for organic or inorganic compounds make circular dichroism (CD) spectroelectrochemistry a suitable tool to determine chiroptical and stereochemical properties of natural and synthetic optically active compounds. In situ ECD spectra of electrochemically generated target species have appeared in several reports on chiroptical activity of redoxactive molecular systems in the UV-Vis spectral region.…”

“…In situ ECD spectra of electrochemically generated target species have appeared in several reports on chiroptical activity of redoxactive molecular systems in the UV-Vis spectral region. [2][3][4] However, such studies are limited to species featuring an optically active chromophore.…”