Synthesis, Characterization, Crystal and Molecular Structure of 1,5-Dihydro-2H-cyclopenta[1,2-b:5,4-b′]dipyridin-2-imine

The reaction of 1,5‐dihydro‐2H‐cyclopenta[1,2‐b:5,4‐b′]dipyridin‐2‐one (3) with an alkylamine (butylamine, hexylamine or ethylenediamine) yields, quite unexpectedly and in the absence of catalyst, the novel compound 1,5‐dihydro‐2H‐cyclopenta[1,2‐b:5,4‐b′]dipyridin‐2‐imine (4) as the sole, analytical...

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Bibliographic Details
Published in:Helvetica chimica acta 2007-06, Vol.90 (6), p.1211-1217
Main Authors: Baysal, Akın, Durap, Feyyaz, Gümgüm, Bahattin, Yıldırım, Leyla T., Ülkü, Dinçer, Boğa, Ayse Dilek, Özkar, Saim
Format: Article
Language:English
Subjects:
Bipyridine
Diazafluorene
Imines
X-Ray crystallography
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Summary:The reaction of 1,5‐dihydro‐2H‐cyclopenta[1,2‐b:5,4‐b′]dipyridin‐2‐one (3) with an alkylamine (butylamine, hexylamine or ethylenediamine) yields, quite unexpectedly and in the absence of catalyst, the novel compound 1,5‐dihydro‐2H‐cyclopenta[1,2‐b:5,4‐b′]dipyridin‐2‐imine (4) as the sole, analytically pure, solid product, which was fully characterized. The structure of 4 was unequivocally solved by single‐crystal X‐ray‐diffraction analysis. The compound crystallizes in a monoclinic cell (space group P 21/c), with two molecules in the asymmetric unit, held together by intermolecular H‐bonds. Compound 4 could be interesting as a bi‐ or even tridentate ligand, and exhibits a strong fluorescence upon excitation at 310 nm. A mechanism, based on the observed CN bond cleavage, is proposed.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.200790120