Organic redox polymers are attractive electrode materials for more sustainable rechargeable batteries. To obtain full-organic cells with high operating voltages, low potentials (<2 V versus Li|Li+) required the negative electrode. Dibenzo[a,e]cyclooctatetraene (DBCOT) is a promising redox-active group in this respect, since it can be reversibly reduced two-electron process at below 1 Li|Li+. Up...

An exhaustive and systematic study of the structural and electronic properties of cyclooctatetraene (COT) upon substitution of hydrogen atoms by fluoro and cyano groups has been carried out in order to analyse the influence of both substituents on the aromaticity. We found that C-C distances decrease with fluoro substitution while in cyano derivatives the opposite happens. All the compounds ret...

A detailed investigation has been made into the antiaromaticity and chemical reactivity of a planar cyclooctatetraene (COT) molecule fully annelated with bicyclo[2.1.1]hexane units 2. In spite of its planar 8pi-electronic structure, theoretical calculations have indicated that the antiaromaticity of COT 2 is considerably decreased in comparison with a planar COT 16 with D 4h symmetry. This beha...

Bright, photostable and non-toxic fluorescent contrast agents are critical for biological imaging. ‘Self-healing’ dyes, in which triplet states intramolecularly quenched, enable fluorescence imaging by increasing fluorophore brightness longevity, while simultaneously reducing the generation of reactive oxygen species that promote phototoxicity. Here, we systematically examine self-healing mecha...

The Baird-aromaticity of BN/CC cyclooctatetraene isosteres (azaboracyclooctatetraenes) in their lowest triplet states (T1) has been explored through computations various aromaticity indices that describe the different aspects (magnetic, electronic, energetic and geometric). While (COT) is aromatic its T1 state following Baird's 4n rule, we now reveal degrees vary with aspect considered. thermod...

The electroreduction of COT in liquid ammonia at -38° and -65°C was investigated by cyclic voltammetric and controlled potential coulometric techniques. The results are interpreted by a two-step two-electron transfer reaction with strong ion-pairing of the COT dianion. Values for the heterogeneous electron transfer rate constants and the equilibrium constant of the disproportionation of the rad...