Electrochemistry of the 9‐phenyl‐10‐methyl‐acridan/acridinium redox system; a high‐potential NADH/NAD<sup>+</sup> analogue

Koper, N. W.; Jonker, Stephan A.; Verhoeven, J. W.; Dijk, C. van

doi:10.1002/recl.19851041106

Cited by 41 publications

(44 citation statements)

References 48 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This spectrum can readily be attributed to the 1 CT state of 9. Its fast rise is in agreement with the virtually complete quenching of the acridinium fluorescence, and the spectrum displays features characteristic for both the neutral acridinyl radical [51] and the naphthalene radical cation, [52] as indicated in Figure 10. It is important to note that in addition to these features the spectrum contains an extra and rather strong absorption around 560 nm which must be the result of interaction between the two constituent moieties.…”

Section: Long-lived Charge Separation In a Compact Zinc Chlorin-c 60 mentioning

confidence: 83%

Long‐Lived Charge‐Transfer States in Compact Donor–Acceptor Dyads

et al. 2005

View full text Add to dashboard Cite

Photoinduced electron transfer is a widely applied method to convert photon energy into a useful (electro)chemical potential, both in nature and in artificial devices. There is a continuing effort to develop molecular systems in which the charge-transfer state, populated by photoinduced electron transfer, survives sufficiently long to tap the energy stored in it. In general this has been found to require the construction of rather complex molecular systems, but more recently a few approaches have been reported that allow the use of much more simple and relatively small electron donor-acceptor dyads for this purpose. The most successful examples of such systems seem to be those that apply "electron spin control" to slow down the spontaneous decay of the charge-transfer state, and these are reviewed in this minireview, with a discussion of the underlying principles and a critical evaluation of some of the claims made with regard to using a pronounced "inverted-region effect" as an alternative method to prolong the lifetime of charge-transfer states.

show abstract

Section: Long-lived Charge Separation In a Compact Zinc Chlorin-c 60 mentioning

confidence: 83%

Long‐Lived Charge‐Transfer States in Compact Donor–Acceptor Dyads

et al. 2005

View full text Add to dashboard Cite

show abstract

“…In contrast to the immediate formation of the rhenium adduct from N-methylacridinium, the corresponding 9-phenyl-N-methylacridinium cation yielded only the dimeric Re 2 (CO) 10 and the persistent 9-phenyl-N-methylacridanyl radical, 36 in quantitative yield, according to the equation…”

Section: Addition and Electron-transfer Reactions Of Re(co)mentioning

confidence: 99%

“…Since the acridanyl radical and Re 2 (CO) 10 were the unambiguous products of one-electron oxidation and reduction of the cation 36 and anion, 14 respectively, the transformation in equation (3) was designated as electron transfer. .…”

Section: Addition and Electron-transfer Reactions Of Re(co)mentioning

confidence: 99%

Nucleophilic addition versus electron transfer in carbonylmetallate salts. Donor-acceptor interactions in the precursor ion pairs

Bockman¹,

Kochi²

1997

J. Phys. Org. Chem.

View full text Add to dashboard Cite

The isostructural pentacarbonylmetallate anions M(CO)ϪϪ 5 ] is identified as the critical precursor for both electron transfer and nucleophilic coupling. Based on these observations, it is proposed that the rates and mechanisms of these interionic reactions are controlled by donor-acceptor bonding in the transition states, which in turn is directly related to the charge-transfer interactions extant in the ion-pair intermediate. ©

show abstract

“…3 can be assigned to the proton (about 0 V) and AcrH + (-0.5 V [9]), respectively, which is formed upon the two electron oxidation of AcrH 2 .…”

Section: Electrochemical Oxidation Of Aryl Cycloheptatrienesmentioning

confidence: 99%

Electrochemical oxidation of aryl cycloheptatrienes

Grubert¹,

Jacobi²,

Abraham³

1999

J. prakt. Chem.

View full text Add to dashboard Cite

The electrochemical oxidation of hydrocarbons proceeds via the radical cation the carbon-hydrogen bonds of which are considerably acid. Generally, the deprotonation of such radical cations plays an important role [1]. In contrast to the cycloheptatriene/tropylium couple [2], redox systems, which can serve as heterocyclic coenzyme analogues such as the acridan/acridinium couple and dihydropyridine/pyridinium systems were intensively studied [3]. The electrochemical generation of aryltropylium ions from arylcycloheptatrienes is of special interest because various molecular properties such as shape, colour and electron acceptor strength differ strongly from those of tropylium cations. Accordingly, the properties of macrocycles [4] and supramolecular systems such as rotaxanes and catenanes containing cycloheptatriene building blocks [5] are expected to undergo significant changes in response to the loss of electrons.As part of our research program concerning the photochemical generation of tropylium cations [6] the electrochemical oxidation was carried out to learn about the behaviour of radical cations produced in the absence of any electron acceptor. For this purpose experiments with cycloheptatrienes 1, 2 and 3 containing aryl substituents of different donor strength and 1,3,5-cycloheptatriene 1a and the methoxy substituted derivative 1b were performed. The compounds 1f -1i were only used to evaluate the influence of the substituents on the oxidation peak potentials (see Fig. 1).Compounds 1d -3d differ from the other cycloheptatrienes studied in their basic properties. This may be meaningful regarding the deprotonation of the related radical cations. Keywords: Electrochemistry, Cyclic Voltammetry, Oxidation, Cycloheptatrienes, Tropylium salts Abstract. The electrochemical oxidation of various substituted aryl cycloheptatrienes and cyclohepta-1,3,5-triene, the parent compound, in acetonitrile is investigated with the aid of cyclic voltammetry (CV), experiments at the rotating ring disk electrode (RRDE) and controlled potential electrolysis. Electrochemical Oxidation of Aryl

show abstract

Electrochemistry of the 9‐phenyl‐10‐methyl‐acridan/acridinium redox system; a high‐potential NADH/NAD⁺ analogue

Cited by 41 publications

References 48 publications

Long‐Lived Charge‐Transfer States in Compact Donor–Acceptor Dyads

Long‐Lived Charge‐Transfer States in Compact Donor–Acceptor Dyads

Nucleophilic addition versus electron transfer in carbonylmetallate salts. Donor-acceptor interactions in the precursor ion pairs

Electrochemical oxidation of aryl cycloheptatrienes

Contact Info

Product

Resources

About

Electrochemistry of the 9‐phenyl‐10‐methyl‐acridan/acridinium redox system; a high‐potential NADH/NAD+ analogue

Cited by 41 publications

References 48 publications

Long‐Lived Charge‐Transfer States in Compact Donor–Acceptor Dyads

Long‐Lived Charge‐Transfer States in Compact Donor–Acceptor Dyads

Nucleophilic addition versus electron transfer in carbonylmetallate salts. Donor-acceptor interactions in the precursor ion pairs

Electrochemical oxidation of aryl cycloheptatrienes

Contact Info

Product

Resources

About

Electrochemistry of the 9‐phenyl‐10‐methyl‐acridan/acridinium redox system; a high‐potential NADH/NAD⁺ analogue