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Intramolecular electron transfer between terminal 1,4-dimethoxybenzene units in radical cations with a [2.2](1,4)naphthalenophane, [2.2](1,4)anthracenophane, and pentacene skeleton

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Wartini,  Alexander R.
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Staab,  Heinz A.
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Neugebauer,  Franz A.
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Citation

Wartini, A. R., Staab, H. A., & Neugebauer, F. A. (1998). Intramolecular electron transfer between terminal 1,4-dimethoxybenzene units in radical cations with a [2.2](1,4)naphthalenophane, [2.2](1,4)anthracenophane, and pentacene skeleton. European Journal of Organic Chemistry, 1998(6), 1161-1170. doi:10.1002/(SICI)1099-0690(199806)1998:6<1171:AID-EJOC1171>3.0.CO;2-#.


Cite as: http://hdl.handle.net/11858/00-001M-0000-002B-243E-4
Abstract
Various radical cations, in which two terminal 1,4-dimethoxybenzene units are anellated to [2.2]paracyclophane (2b•+, 3b•+), [2.2](1,4)naphthalenophane (4d•+), and anthracene bridges (5•+), have been studied by ESR and ENDOR spectroscopy. In the syn- and anti-naphthalenophane radical cations 2b•+ and 3b•+ the delocalization of the unpaired electron over both π-moieties and the distinct difference between the first and second oxidation potentials, ΔE = E20 – E10, are evidence for a substantial intramolecular electronic interaction between the two electrophores. Extension of the bridge in 4d•+ and 5 by benzo anellation results in a localized radical cation. Strong intramolecular electronic interaction between the two electrophores is found in the 1,4,8,11-tetramethoxy-pentacene radical cation (5•+). The syntheses of 4d are described.