Synthesis, Self‐Assembling and Redox Properties of 2‐[(ω‐Sulfanylalkyl)amino]‐1,4‐naphthoquinones.

Abstract

Sulfur compounds Q 0980 Synthesis, Self-Assembling and Redox Properties of 2-[(ω-Sulfanylalkyl)amino]-1,4-naphthoquinones. -(KAZEMEKAITE, M.; RAILAITE, V.; BULOVAS, A.; TALAIKYTE, Z.; NIAURA, G.; RAZUMAS, V.; BUTKUS*, E.; Collect. Czech.

Electron transfer of quinone self-assembled monolayers on a gold electrode

“…The electron transfer depending on the distance has been also studied by using SAMs bound to redox moieties such as hydroquinone [15], naphthoquinone (NQ) [2][3][4] and azobenzene [16]. In the SAMs including quinone derivatives, proton transfer is essentially involved in the electron transfer process in aqueous solution.…”

“…The electron transfer for SAM of various compounds with redox moieties on a gold electrode has been studied so that the rate constant is found to increase with decreasing the distance between the redox group and the electrode according to the Marcus theory [2][3][4][5][6][7][8][9][10][11][12][13].…”

“…The SAMs on a gold electrode by using alkylthiols and dialkyldisulfides of various alkyl chain lengths were very useful for controlling the distance between the quinone moiety and the electrode surface. It is interesting to note that the effects of the quinone structure and the distance on the electron-transfer rate between the quinone and electrode can be easily examined by using SAM of quinone derivative on a gold electrode [2][3][4].…”

“…In the biological process, quinone pigments play a key role in the electron and proton transfers [1]. Recently, electron transfer in a self-assembled monolayer (SAM) of quinone derivative on a gold electrode has been reported to clarify the electron transfer on the surface of the electrode [2][3][4]. The SAMs on a gold electrode by using alkylthiols and dialkyldisulfides of various alkyl chain lengths were very useful for controlling the distance between the quinone moiety and the electrode surface.…”

Lipophilic 1,4-naphthoquinone derivatives: synthesis and redox properties in solution and entrapped in the aqueous cubic liquid-crystalline phase of monoolein

“…The redox activity of physiological molecules like ubiquinone-10 (UQ 10 ) or plastoquinone-9 (PQ 9 ), solubilized in hydroxylic solutions, has been examined (Okamura and Feher, 1992). Various self-assembly methods were used to incorporate ubiquinones or plastoquinones at the interface between water and modified electrodes, either by means of direct adsorption at the electrode surface (Gordillo and Schiffrin, 1994) or by incorporation into alkanethiol monolayer (Takehara et al, 1991) it has been shown that newly synthesized 1,4-naphthoquinones linked via nitrogen atom through the short chain to the terminal sulfanyl group form self-assembled monolayers on gold electrode (Kažemėkaitė et al, 2006). Numerous model membrane systems have been developed for the studying the physicochemical behavior of quinone molecules inside a bilayer (Gennis, 1989).…”