Reversible dimerization of the anion radicals of some dicyanonaphthalenes

Dicyano- and tetracyanopentacene: foundation of an intriguing new class of easy-to-synthesize organic semiconductors

“…This stabilization of 0.23 eV may be attributed to a reversible dimerization of the radical anions, which has been reported for several smaller cyanated acenes. 19 , 20 In contrast to our experiments, these measurements were carried out in solution, and a significantly larger stabilization of about 0.6 to 0.8 eV has been observed. The reversible bleaching of the otherwise deeply blue TCP thin-film, which was observed upon reduction (Fig.…”

Reversible Redox Switching of Chromophoric Phenylmethylenepyrans by Carbon–Carbon Bond Making/Breaking

“…Supramolecular approaches involving large amplitude motion of their inner components, such as observed in mechanically interlocked molecular (MIM) switches, have been widely developed over the past years, leading to a wide range of functionalized systems including coordination metal complexes and purely organic systems. − Alternatively, organic chromophores displaying low-amplitude motion have also drawn interest when fast switching time is requested. Devices based on the photoactivated switching between two isomers, such as azobenzenes, have been well developed over the past years. , Redox-triggered switches displaying reversible π- or σ-dimerization from electrochemically or photochemically generated radical anions or cations have also drawn interest. − In particular, intermolecular σ C–C dimerization of radical cations of conjugated aromatic systems, such as stilbene, triarylamines, , pyridine, cyanins, dialkoxyanthracene, spiropyran, , tripyrrolinidobenzene, bis­(benzodithiolyl)­bithienyl, and dithiafulvene − were reported. It is noteworthy that recent investigations have focused on the immobilization of this family of redox switches on solid surfaces for the development of smart multiple responsive materials. ,− …”

Integral equation-based simulation of transient experiments for an EC2 mechanism: Beyond the steady state simplification

“…For species B, we employed two approximate approaches valid in the limit of large κ, as already mentioned in the introduction. Approach 1 utilized the steady state relationship (6), which for (11) (with m = 2) and ( 22) yields c B (0, t) = 3 2κ…”

“…However, it is of considerable interest to organic electrochemistry, since dimerization often accompanies free radical formation [6]. Examples of studies where this mechanism (and its somewhat more general variant involving a reversible dimerization) was identified, are in [7][8][9][10][11][12][13]. This list of references is not intended to form an exhaustive review.…”

“…Integral equation-based simulation of transient experiments for an EC2 mechanismApproach 2 utilized the concentration-flux relationship (7) that for(11) (with m = 2) and (22) yields ∂c B (0,…”