title: Promising fast energy transfer system via an easy synthesis: Bodipy-porphyrin dyads connected via a cyanuric chloride bridge, their synthesis, and electrochemical and photophysical investigations.
abstract: The boron dipyrrin (Bodipy) chromophore was combined with either a free-base or a Zn porphyrin moiety (H(2)P and ZnP respectively), via an easy synthesis involving a cyanuric chloride bridging unit, yielding dyads Bodipy-H(2)P (4) and Bodipy-ZnP (5). The photophysical properties of Bodipy-H(2)P (4) and Bodipy-ZnP (5) were investigated by UV-Vis absorption and emission spectroscopy, cyclic voltammetry, and femtosecond transient absorption spectroscopy. The comparison of the absorption spectra and cyclic voltammograms of dyads Bodipy-H(2)P (4) and Bodipy-ZnP (5) with those of their model compounds Bodipy, H(2)P, and ZnP shows that the spectroscopic and electrochemical properties of the constituent chromophores are essentially retained in the dyads indicating negligible interaction between them in the ground state. In addition, luminescence and transient absorption experiments show that excitation of the Bodipy unit in Bodipy-H(2)P (4) and Bodipy-ZnP (5) into its first singlet excited state results in rapid Bodipy to porphyrin energy transfer-k(4) = 2.9 × 10(10) s(-1) and k(5) = 2.2 × 10(10) s(-1) for Bodipy-H(2)P (4) and Bodipy-ZnP (5), respectively-generating the first porphyrin-based singlet excited state. The porphyrin-based singlet excited states give rise to fluorescence or undergo intersystem crossing to the corresponding triplet excited states. The title complexes could also be used as precursors for further substitution on the third chlorine atom on the cyanuric acid moiety.
authors.affiliation: Laboratory of Bioinorganic Chemistry, Chemistry Department, University of Crete, Voutes Campus, P.O. Box 2208, 71003 Heraklion, Crete, Greece.
authors.forename: Theodore
authors.initials: T
authors.lastname: Lazarides
authors.forename: Georgios
authors.initials: G
authors.lastname: Charalambidis
authors.forename: Alexandra
authors.initials: A
authors.lastname: Vuillamy
authors.forename: Marius
authors.initials: M
authors.lastname: Réglier
authors.forename: Emmanuel
authors.initials: E
authors.lastname: Klontzas
authors.forename: Georgios
authors.initials: G
authors.lastname: Froudakis
authors.forename: Susanne
authors.initials: S
authors.lastname: Kuhri
authors.forename: Dirk M
authors.initials: DM
authors.lastname: Guldi
authors.forename: Athanassios G
authors.initials: AG
authors.lastname: Coutsolelos
mesh_terms: D001896:Boron Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D055664:Electrochemical Techniques; D004735:Energy Transfer; D008958:Models, Molecular; D011166:Porphyrins / Q000138:chemical synthesis / Q000737:chemistry*; D013057:Spectrum Analysis
chemical_list: D001896:Boron Compounds; D011166:Porphyrins