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Synthesis and Electrochemical Properties of New C 60 ‐Acceptor and ‐Donor Dyads
Author(s) -
Diekers Michael,
Hirsch Andreas,
Pyo Soomi,
Rivera José,
Echegoyen Luis
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199806)1998:6<1111::aid-ejoc1111>3.0.co;2-b
Subject(s) - chemistry , electrochemistry , acceptor , fullerene , photochemistry , combinatorial chemistry , organic chemistry , electrode , physics , condensed matter physics
The synthesis of new C 60 ‐acceptor and C 60 ‐donor dyads 6−8 by facile and irreversible [4+2]cycloadditions of anthraquinone‐ and anthraquinodimethane‐based dienes with C 60 , as well as by direct oxidative amination of C 60 with N, N′ ‐dimethyl‐ o ‐phenylenediamine is described. The complete electrochemical characterization and ESR‐spectroscopic data of the C 60 ‐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 C 60 , 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 C 60 ‐acceptor dyad 7 and the C 60 ‐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.