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π…︁π interactions of flavins, 5. Syntheses, structures and physical properties of flavin systems with covalent bonding to π donors and π acceptors (quinones)
Author(s) -
Staab Heinz A.,
Kanellakopulos Johannes,
Kirsch Peer,
Krieger Claus
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199510256
Subject(s) - flavin group , chemistry , intramolecular force , covalent bond , benzoquinone , redox , electrochemistry , photochemistry , stereochemistry , organic chemistry , electrode , enzyme
Abstract To study π…π interactions of flavins of different redox states with π‐electron donors and acceptors, the syntheses of compounds in which such π systems are linked to flavins by using the „cyclophane concept” were attempted and partially achieved. The syntheses of the metacyclo‐isoalloxazinophanes 1 and 2 are reported as well as the X‐ray structure analysis of 2. The conversion of 1 or 2 to the benzoquinono‐isoalloxazinophanes 3 or 4 , respectively, was not achieved, obviously due to the specific sterical shielding of the methoxy groups in the isoalloxazinophanes. Benzoquinone‐isoalloxazine systems in which the two components are linked by only one triethylene chain were obtained. Spectroscopic and electrochemical properties related to intramolecular interactions are reported.