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Electron Donor-Acceptor Compounds, XXXVIII. Electron Donor-Acceptor Metacyclophanes: Synthesis, Structure, and Charge-Transfer Spectra
Staab, Heinz A.,Schanne, Lothar,Krieger, Claus,Taglieber, Volker
, p. 1204 - 1229 (2007/10/02)
Donor-acceptor metacyclophanes 1-4 as well as 24 were synthesized via the correspondingly substituted 2,11-dithiametacyclophanes 8, 13, and 25 and their disulfone derivatives.The anti-compound 1 and the syn-isomer 2 were isolated and characterized.The attempt of the analogous synthesis of 5/6 via 21 and 22 failed since with loss of the intraanular substituents and by transanular C-C formation the tetrahydropyrene derivative 23 was formed.For spectroscopic comparison 27 was prepared via 28.- X-Ray structure analyses of 21, 24, and 25 were performed.The molecular structures of these compounds are discussed under the aspects of sterical strain and donor-acceptor overlap.The structure analyses confirm the assignment to the syn- and anti-series as derived from 1H NMR.- Absorption spectra of 1, 2, 3, and 24 were measured; especially the surprising absorption behaviour of the isomers 1 and 2 with very different donor-acceptor overlap was of interest.Determination of the solvent dependence of fluorescence made sure that the absorptions dealt with are indeed charge-transfer transitions.
