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Annulated Heteroc y clic Derivatives of 1,3,6,8‐Tetraazapyrene (Eur. J. Org. Chem. 24/2013)
Author(s) -
Martens Susanne C.,
Hahn Lena,
Lombeck Florian,
Rybina Arina,
Wadepohl Hubert,
Gade Lutz H.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201390067
Subject(s) - indolizine , chemistry , trifluoroacetic anhydride , pyridine , intramolecular force , homo/lumo , molecule , photochemistry , stereochemistry , medicinal chemistry , organic chemistry
The cover picture shows a highly fluorescent polyheterocyclic aromatic compound, dissolved in solvents of varying polarity, which combines the electron‐poor 1,3,6,8‐tetraazapyrene (TAPy) unit with electron‐rich indolizine, thus representing an electronic push–pull system. The HOMO is located on the indolizine part of the molecule, whereas the LUMO primarily resides on the tetraazapyrene unit, which implies considerable intramolecular charge transfer for the corresponding π*←π transition. Such compounds are obtained as side products in the synthesis of a 1,3,6,8‐tetraazapyrene by conversion of the tin “double salt” of tetraaminonaphthalene hydrochloride with trifluoroacetic anhydride in pyridine. Their electro‐ and photochemical properties are discussed in the article by L. H. Gade et al. on page 5295 ff.