hide
Free keywords:
-
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.
