ISBN: 978-83-60043-10-3 - eurobic9

Eurobic9, 2-6 September, 2008, Wrocław, Poland
P2. Synthesis, Structure and Spectroscopic Studies on New Derivatives of 2acetyl-1,
3-indandione, Coupled with Crown Ether,
as Potential Sensors for Metal Ions
A. Ahmedova a , N. Burdjiev a , S. Ciattini b , M. Mitewa a
a Faculty of Chemistry , University of Sofia, J. Bourcher av. 1, Sofia 1164, Bulgaria
e-mail: Ahmedova@chem.uni-sofia.bg
b Dipartimento di Chimica, Universita` degli Studi di Firenze, Via della Lastruccia 3, I-50019 Sesto Fiorentino
(FI), Italy
The parent compound, 2-acetyl-1, 3-indandione (2AID), is known for its physiological activity and interesting
photophysical properties. Recently the potential application of cinnamoyl derivatives of 2AID as anti HIV agents
has been suggested. Moreover, 2-acyl-1, 3-indandiones are very good chelating agents for heavy and transition
metal ions due to the β–dicarbonyl fragment they posses and have found practical application as extracting
agents for metal ions.
Present report deals with a 2-cinnamoyl derivative of 2AID (depicted in the Figure and R = N(Me)2; compound
1) and a 1, 3-indandione derivative directly conjugated with N-penylaza-15-crown-5 (compound 2). As might be
expected, the conjugation of a strong electron acceptor, such as 2AID, with a strong electron donor groups, as
dialkyl amino groups, results in very strong absorption in the visible region of the spectrum.
In combination with their very good ability for chelation with metal ions the studied organic compounds can
be exploited for development of real-time methods for metal ion sensing and their quantitative determination.
In this respect, the synthesis of the ligands and their metal complexes is described as well as structural
elucidation of the obtained compounds. Further on the optical (absorption and emission) properties of the
organic compounds are studied in detail accounting for various effects, such as aggregation, pH, solvent effect
and mainly the presence of metal ions.
As a result of all the data obtained a final assessment of the new compounds as potential optical sensors for
metal ions is given. All potential fields of applications and their limitations are discussed.
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