Radikalanionensalze von Naphthalintetracarbonsäure‐Derivaten – eine neue Klasse elektrisch leitfähiger Verbindungen

Heywang, Gerhard; Born, Liborius; Fitzky, H. G.; Hassel, Tillmann; Hocker, J.; Müller, H.; Pittel, B.; Roth, S.

doi:10.1002/ange.19891010409

Cited by 8 publications

(4 citation statements)

References 7 publications

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“…Although the first wave is perfectly reversible (in the sense that the peak separation for the reductions is exactly 60 mV), the second reduction is slightly less reversible (peak separation 120 mV). Apparent E ° values in Table were taken as the center of the anodic and cathodic peak potentials and are consistent with those reported for other aromatic imides 12b. Compounds 4 , with quaternary ammonium groups, had reduction potentials at slightly more positive potentials, −0.40 and −0.85 V, but both reduction processes were strongly irreversible, with dependence on the sweeping rate (peak separation >180 and 300 mV at 200 mV/s).…”

Section: Resultssupporting

confidence: 77%

“…The reduction of 4 in 1:1 CH 3 CN/H 2 O bleached the reactant absorbance (360 and 378 nm), generating a new species with maximum absorbance centered at 458 nm (Figure a). Such a transient was assigned to the radical anion of the diimide 4 ( 4 • - ) on the basis of (i) its rapid quenching in the presence of O 2 , (ii) the spectroscopic similarity to NDI radical anions, bearing cationic substituents to the imide nitrogen atom [such as −(CH 2 ) n NMe 3 + (λ max 449 nm)],12b generated by electrochemical reduction and by intramolecular photoinduced single electron transfer . The radical anion 4 • - decays with a first-order kinetic ( k 1 = 8.1 × 10 -4 s -1 , r 2 = 0.99), in the absence of O 2 , to generate another species with absorbance centered at 412, 542, and 590 nm (Figure b).…”

Section: Resultsmentioning

confidence: 99%

“…The latter moiety may act simultaneously as the molecular recognition structural element and substituent on a QMP, with electron donor/acceptor properties tunable by reduction (owing its redox properties) and upon base catalysis (due to its acidity). In fact, it is well-known that naphthalene diimide derivatives can be easily reduced to a radical anion by electrochemical means 3 Synthesis of 4 …”

Section: Introductionmentioning

confidence: 99%

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Novel Naphthalene Diimides as Activatable Precursors of Bisalkylating Agents, by Reduction and Base Catalysis

et al. 2007

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Mild activation of water-soluble naphthalene diimides (NDIs) as bisalkylating agents has been achieved by base catalysis and by chemical and electrochemical reductions. NDI activation by a single electron reduction represents a novelty in the field of activatable electrophiles. Under mild reduction, induced by S2O4(2-) in aqueous solution, the resulting NDI radical anion (NDI*-) undergoes a monomolecular fragmentation to yield a new transient species, where the NDI radical anion is tethered to a quinone methide moiety. The latter still retains electrophilic properties, reacting with amines, thiols, and ethyl vinyl ether. Owing to the NDI recognition properties, these results represent the first step toward selective and bioactivatable cross-linking agents.

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Section: Resultssupporting

confidence: 77%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Novel Naphthalene Diimides as Activatable Precursors of Bisalkylating Agents, by Reduction and Base Catalysis

et al. 2007

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“…The effect of Nsubstitution is perhaps greater than might be expected since the MO descriptions of aromatic imides have a node at nitrogen, [12] implying that N-substituents should perhaps only weakly affect the LUMO energy, a parameter directly related to the first reduction potential of the substrate. [11] However, it is clear from the values in Table 1 that the inductive effects of the substituents play an important role in determining the values of the redox potentials for both pyromellitic and naphthalene diimide derivatives.…”

Section: Electrochemistrymentioning

confidence: 97%

Photophysical and Electrochemical Characterisation of the Interactions between Components in Neutral π-Associated [2]Catenanes

et al. 2000

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The electrochemical and photophysical properties of a variety of neutral pi-associated [2]catenanes have been explored by using cyclic voltammetry, absorption and luminescence spectrophotometry and the measurement of exited-state lifetimes. Several trends that could be correlated with interactions between the mechanically linked components of the structures were revealed from comparative study of catenane precursors, model compounds and the [2]catenanes themselves. Throughout, emphasis is placed on pair-wise comparisons between systems which differ in a single structural feature. Substitution in a catenane of a pyromellitic diimide unit by a naphthalene diimide yields more readily reduced derivatives, whose absorption spectra reveal charge transfer within the catenane to be a lower energy process of reduced intensity. Conversion of the butadiyne links within the diimide macrocycle of the catenanes to saturated chains results in an increase in both the energy and intensity of their charge-transfer bands; electrochemically these derivatives are all harder to reduce than the parent systems. Replacement of one of the electron-donating components of the catenanes with a less effective aromatic donor bearing a carboxy group also decreases the energy and intensity of the charge-transfer feature and is accompanied by a slightly more ready reduction. A sequence of reduction and translational events is proposed to explain the intriguing electrochemical behaviour of a catenane that contains one pyromellitic and one naphthalene diimide. For some systems the photophysical and electrochemical techniques, whilst exploring distinct physical phenomena, are shown to be in good agreement by comparison of shifts of electrochemical reduction waves with those of charge-transfer absorption features.

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Naphthalimide Dyes and Pigments

Haremsa¹

2000

Ullmann's Encyclopedia of Industrial Chemistry

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The article contains sections titled: 1. Introduction 2. Alkoxynaphthalimides 3. 4‐Aminonaphthalimides 4. 1′,8′‐Naphthoylenebenzimidazoles 5. Imides of Naphthalene‐1,4,5,8‐tetracarboxylic Dianhydride 6. 1′,8′‐Naphthoylenebenzimidazole Peridicarboximides 7. Bis‐benzimidazole Derivatives of Naphthalene‐1,4,5,8‐tetracarboxylic acid 8. 1′,8′‐Naphthoylenepyrazoles 9. Benzo[ k,l ‐]xanthene‐ and Benzo[ k,l ‐]thioxanthene‐3,4‐ dicarboximides 10. Azo‐ and Azomethinenaphthalimides 11. Perylene‐3,4,9,10‐tetracarboxydiimides

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Radikalanionensalze von Naphthalintetracarbonsäure‐Derivaten – eine neue Klasse elektrisch leitfähiger Verbindungen

Cited by 8 publications

References 7 publications

Novel Naphthalene Diimides as Activatable Precursors of Bisalkylating Agents, by Reduction and Base Catalysis

Novel Naphthalene Diimides as Activatable Precursors of Bisalkylating Agents, by Reduction and Base Catalysis

Photophysical and Electrochemical Characterisation of the Interactions between Components in Neutral π-Associated [2]Catenanes

Naphthalimide Dyes and Pigments

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