A Redox-Controlled Molecular Switch Based on the Reversible C−C Bond Formation in Octamethoxytetraphenylene

Synthesis and Characterization of Novel Chiral Conjugated Materials

“…The cyclic voltammetric data were consistent with the reversible CC bond formation. Dication 75 2+ .2SbCl 6 -was isolated and its hexacyclic structure was unequivocally determined by X-ray crystallography (Figure 15.28) [113].…”

“…Oxidation of 56 to dication gives irreversible cyclic voltammetry, which was qualitatively similar to that found by Kochi and coworkers for the achiral tetraarylene 75 [113]. The cyclic voltammetric data were consistent with the reversible CC bond formation.…”

Insights into the radical-radical and radical-substrate dimerization processes for substituted phenylmethylenepyrans

“…Different types of organic dimers can be found according to the mode of interaction between monomeric units, upon redox activation. Most of studies have been focused on organic dimers generated by the formation of σ-σ carbon-carbon bond [9][10][11]. Also, π-π dimers have been more recently developed with supramolecular organic systems [12][13][14][15].…”

“…Electronic structure M A N U S C R I P T A C C E P T E D ACCEPTED MANUSCRIPT 2 calculations show that the spin population in the radical cation and the strength of the σ-σ C-C bond in the dimer strongly depend on the nature of R. In addition, low-temperature electrochemical voltammetry (175 K), and room-temperature high scan rate cyclic voltammetry have been used to unravel the kinetics of the C-C bond formation. Keywords : radical dimerization ; methylenepyran ; low-temperature voltammetry ; C-C bond making ; ab initio calculations.applications in the domain of redox switches and electrochromic devices for systems displaying optical properties in the UV-Visible spectroscopic domain [9,11,[16][17][18][19][20]. Among them, methylenepyrans (MPs) are organic molecules which have been fully exploited as dyes for photovoltaic cells [21], but also as component parts of push-pull compounds for non-linear optic (NLO) applications and luminescent devices [22][23][24].…”

“…applications in the domain of redox switches and electrochromic devices for systems displaying optical properties in the UV-Visible spectroscopic domain [9,11,[16][17][18][19][20]. Among them, methylenepyrans (MPs) are organic molecules which have been fully exploited as dyes for photovoltaic cells [21], but also as component parts of push-pull compounds for non-linear optic (NLO) applications and luminescent devices [22][23][24].…”