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[3.3]Isoalloxazinophanes and arene-bridged bis(isoalloxazines): syntheses, characterizations and properties related to intramolecular interactions

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

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Kirsch,  Peer
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Zipplies,  Matthias F.
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Weinges,  Alexa
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Krieger,  Claus
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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http://onlinelibrary.wiley.com/doi/10.1002/cber.19941270917/epdf
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https://dx.doi.org/10.1002/cber.19941270917
(Any fulltext)

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Citation

Staab, H. A., Kirsch, P., Zipplies, M. F., Weinges, A., & Krieger, C. (1994). [3.3]Isoalloxazinophanes and arene-bridged bis(isoalloxazines): syntheses, characterizations and properties related to intramolecular interactions. Chemische Berichte, 127(9), 1653-1665. doi:10.1002/cber.19941270917.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0019-A8CE-F
Abstract
In order to study the orientation and distance dependence of π … π interactions between flavins in various redox states, two approaches to bis(isoalloxazine) model compounds are presented: The [3.3]isoalloxazinophanes 2 and 4 and the rigid single-bridged 1,8-naphthalene- and 1,8-anthracene-linked bis(isoalloxazine) systems 6, 8 and 26 were synthesized, characterized, and studied by spectroscopic methods and cyclic voltammetry. The experimental data are discussed in comparison with “monomeric” isoalloxazines and flexible single-chain trimethylene-linked bis(isoalloxazine) reference compounds. X-Ray structure analyses are reported for the 1,8-bis(isoalloxazinyl)-9,10-dihydroanthracene 26 and for 22 as an example of 1,8-disubstituted naphthalenes with strongly polar substituents comparable to 6.