С-ОН bond cleavage initiated by electron transfer: electroreduction of 9-fluorenol

Supramolecular D⋯A-layered structures based on germanium complexes with 2,3-dihydroxynaphthalene and N,N′-bidentate ligands

“…As an example of a similar structural motif that reversibly attaches two electrons, we can mention the fluorenone. 29 …”

“…As an example of a similar structural motif that reversibly attaches two electrons, we can mention the uorenone. 29 The results obtained can be compared with the electroreduction of chlorogermanes in the presence of 2,2 0 -bipyridine, 10 where the potential shi for various objects was also about 1 V. Comparable values of potential shis are observed in case of nicotinamide and isoniazid and their complexes with 3,5-di-tert-butyl germanium catecholate. 30 In case of nicotinic acid 30 and 3-and 4-cyanopyridines, the potential shi is 0.4-0.6 V. 31 At the same time, in all cases, complete chemical reversibility of electroreduction is not observed.…”

Upconversion of Reductants

“…The two useful design strategies for dissociative reductive upconversions often include starting with a high‐energy labile bond and forming a stable coproduct. The search for suitable labile bonds is facilitated by the fact that dissociative electron‐transfer reactions have been studied in sufficient detail and—apart from the above examples with the cleavage of N−O, N−S, or O−O bonds—have also been reported for S−S, C−S, C−O, and C−C bonds . Both molecular nitrogen and carbon dioxide are viable choices as a possible stable coproduct.…”

Reversible Hydrogen Releasing and Fixing with Poly(Vinylfluorenol) through a Mild Ir‐Catalyzed Dehydrogenation and Electrochemical Hydrogenation

“…The reactivity of both the hydroxyl group and the hydrogen atom at the 9‐position of fluorene are enhanced due to the presence of the cyclopentane moieties of fluorenol, and among other applications, these compounds have been studied as especially biomarkers and fluorescent dyes . The aromaticity of the fluorene skeleton also makes the fluorenol derivative relatively highly acidic; the acid dissociation constants of the hydroxyl group and of the hydrogen atom at the 9‐position were reported to be 10.3 and 8.9, respectively, which are much larger than those of aliphatic alcohols and comparable to those of phenols . Polymers containing the 9‐substituted fluorene derivative unit have been synthesized as dyes and fluorescent materials for applications in organic solar cells and sensors, and these polymers are often substituted with bulky alkyl groups.…”