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From Byproducts to Efficient Fluorophores: A Route to the Synthesis of Fluorubines
Author(s) -
Fleischhauer Jan,
Beckert Rainer,
Jüttke Yvonne,
Hornig David,
Günther Wolfgang,
Birckner Eckhard,
Grummt UlrichW.,
Görls Helmar
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901961
Subject(s) - cationic polymerization , chemistry , quinoxaline , combinatorial chemistry , mass spectrometry , oxalic acid , derivative (finance) , ring (chemistry) , elemental analysis , chemical transformation , fluorescence , organic chemistry , chromatography , financial economics , economics , physics , quantum mechanics
The reaction of bis(imidoyl) chlorides of oxalic acid with monoalkyl hydrazines leads to substituted Δ 2 ‐1,2‐diazetines, which are versatile building blocks for ring‐transformation reactions. One remarkable product originating from side reactions featured by a strong orange/red fluorescence was confirmed as a novel fluorubine derivative. In continuing our studies to substituted oligoazaacenes, we developed several synthetic entries to build up novel fluorubine derivatives, in which particularly aminobridged bis(quinoxaline)s are the key products for cationic hexaazapentacenes. We would like to discuss the possible formation pathways of these fluorubine derivatives, which exhibit interesting photophysical and chemical properties. The structures of all new derivatives were confirmed by common analytical methods (NMR spectroscopy, CV, UV/Vis, mass spectrometry, elemental analysis, and X‐ray structural analysis) and will be discussed on selected examples in more detail.