ISSN:
1434-193X
Keywords:
Cyclic voltammetry
;
Donor-acceptor systems
;
EPR spectroscopy
;
Fullerenes
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The synthesis of new C60-acceptor and C60-donor dyads 6-8 by facile and irreversible [4+2]cycloadditions of anthraquinone- and anthraquinodimethane-based dienes with C60, as well as by direct oxidative amination of C60 with N, N′-dimethyl-o-phenylenediamine is described. The complete electrochemical characterization and ESR-spectroscopic data of the C60-acceptor dyads allows an unambiguous assignment of the location of each reduction step to one or other of the electroactive groups. The locations of the first oxidation and reduction events in all type A and -B systems investigated in this study correspond to the PM3-calculated HOMOs of the neutral species or the SOMOs of the singly reduced species. Whereas the anthraquinone moiety in 6 is a weaker acceptor than C60, the introduction of the more electron-withdrawing cyanoimino groups at the 9,10-positions of the anthracene unit in the dyad 7 causes the first reduction to take place on the addend. This experimental and computational study has shown that both the C60-acceptor dyad 7 and the C60-donor dyad 8 are suitable precursors for the synthesis of the proposed type-D triads, which contain both a donor and an acceptor building block attached to the fullerene core in a stereochemically defined arrangement.
Type of Medium:
Electronic Resource
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