International Summer School PROGRAM - Laboratoire d'Infochimie ...

1
Synthesis and Cation-Dependent Photophysical Properties of
Crown-Containing 1,8-Naphthalimide Derivatives
P. A. Panchenko 1 *, Yu. V. Fedorov 1 , O. A. Fedorova 1 , G. Jonusauskas 2
Institute of Organoelement Compounds of Russian Academy of Sciences, Vavilova 28,
Moscow, 119991, Russia. E-mail: pavel@ineos.ac.ru
2
Centre de Physique Moléculaire Optique et Hertzienne (CPMOH), UMR CNRS 5798,
Université Bordeaux 1, 351, Cours de la Libération, 33405 Talence, France
During the last years, much attention has been paid to the design, synthesis and
characterization of photochemical molecular devices, which combine chromophore
signaling units and receptor groups capable of binding of molecules and ions. Such
devices can find employment in many disciplines such as biochemistry, clinical and
medical sciences, analytical chemistry and environmental science.
Naphthalimide derivatives with EDG at the 4-th position of naphthalene ring are
well known organic chromophores and fluorophores showing good photostability and
strong emission and absorption bands in the visible region. Thus, this type of
compounds has been successfully used as signaling units for the design of ion-active
molecular systems.
R = H, Ac
RHN
Ar =
PET FRET
O
O
N Ar
O
H 2 N
O
O
N
O
O
O O
O
H
N
O
N
O
O
O
N
O O
The present paper reports synthesis and investigation of spectral properties of
naphthalimides containing crown ether substituents in N-aryl moiety. Compounds under
study were found to respond to the presence of metal ions in MeCN solution via the
enhancement of fluorescence intensity. The observed spectral effects were attributed to
inhibition of PET process between naphthalimide chromophore and electron donating
N-aryl group upon the complex formation. It was also demonstrated that the efficiency
of energy transfer (FRET, Förster Resonanse Energy Transfer) between naphthalimide
units in crown ether containing bis(chromophore) systems can be operated by the
addition of metal ions.
Ar