ISMSC 2007 - Università degli Studi di Pavia

Tetra-Cationic phthalocyanines
Yasin Arslanolu, Esin Hamuryudan*
Technical University of Istanbul, Department of Chemistry, 34469, Istanbul, Turkey,
Fax:(+90) 212 285 63 86, e-mail: arslanoglu@itu.edu.tr
PSA 5
Metallophthalocyanines (PcMs) have been widely studied for many years, mainly for their
properties as dyes and catalysts. The recent advances in materials science have identified
many new applications for PcMs as active materials in various fields, for example in nonlinear
optical (NLO) devices as semiconducting materials, as liquid crystals, photosensitizers and
electrochromic devices, amongst others. PcMs possess an extended network of -electrons,
have planar or nearly planar structures in many cases, and show high thermal and
photochemical stabilities. Since most PcMs are insoluble, and therefore difficult to process, the
introduction of substituents at the Pc ring is a necessary approach to increase their solubility.
The synthesis and characterization of metalophthalocyanines tetra-substituted with
dimethylaminoethylsulfanyl groups on peripheral positions were achieved by cocyclotetramerization
of 4-(2-dimethylaminoethylsulfanyl)-1,2-dicyanobenzene with paramagnetic
metal salts (CoCl2,CuCl2 etc...). Compounds were characterized by their elemental analysis,
UV-Vis, FT-IR, and mass spectroscopic methods. The study of their ESR and chemical
properties is now in progress and the results will be published elsewhere .
[1] Dabak S, Gumus G, Gul A, and Bekaroglu O. J. Coord. Chem. 1996, 38, 287-293.
[2] Y. Arslanolu and E. Hamuryudan Dyes and Pigments, 2007, 75, 150-155.
[3] Law, W.F.; Liu, R.C.W.; Jiang, J.; Ng, D.K.P. Inorganica Chimica Acta, 1997, 256,147-150.
PSA 6
Water Soluble, NIR Emitting Boradiazaindacene Dyes as Fluorescent Ion
Sensors
Serdar Atilgan, Tugba Ozdemir and Engin U. Akkaya*
Middle East Technical University, Department of Chemistry, 06531 Ankara, Turkey.
Boradiazaindacenes (a.k.a. BODIPY) found applications in diverse array of fields.
Distyryl-boradiazaindacenes are especially promising considering their long wavelength
absorption (650-685 nm, typically) and emission characteristics. We have recently
demonstrated that a water soluble distyryl-boradiazaindacene derivative (1) showed a
remarkable photodynamic activity.[1] Water solubility is an important issue in designing
practically useful fluorescent chemosensors, as well. In this study, well-known aryldipicolylamine
group has been incorporated into a distyrl-boradiazaindacene structure. In
addition, the chemosensor 2 carries six TEG (triethyleneglycol) units to improve solubility.
Metal ion binding is signalled by a hypsochromic shift and increase in emission intensity. The
design, synthesis and characterization of the chemosensor will be presented.
[1] Atilgan, S.; Ekmekci, Z.; Dogan, A. L.; Guc, D.; Akkaya, E. U. Chem. Commun. 2006, 4398-
4400.