Ultrafast charge transfer in amino-substituted boron dipyrromethene dyes and its inhibition by cation complexation: A new design concept for highly sensitive fluorescent probes

Kollmannsberger, Matthias and Rurack, Knut and Resch-Genger, Ute and Daub, Jörg (1998) Ultrafast charge transfer in amino-substituted boron dipyrromethene dyes and its inhibition by cation complexation: A new design concept for highly sensitive fluorescent probes. JOURNAL OF PHYSICAL CHEMISTRY A, 102 (50). pp. 10211-10220. ISSN 1089-5639, 1520-5215

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Abstract

The photophysical behavior of a newly synthesized aza crown-substituted boron-dipyrromethene (BDP) dye and its dimethylamino analogue were investigated with steady-state and time-resolved fluorometry and compared to a reference compound. In solvents more polar than hexane, excitation of the dyes leads to a fast charge transfer from the locally excited (LE) state to a weakly emissive charge-transfer (CT) state. The donor-substituted compounds show dual emission from the LE and CT state, both fluorescence quantum yields being low. The rate constant of excited-stare charge separation, calculated from the global analysis of time-resolved emission data, was determined to 1.6 x 10(11) s(-1) in 1,4-dioxane. The crowned compound forms 1:1-complexes with various alkali and alkaline-earth metal ions, which exist as two conformers in solution. In these complexes, coordination of the cation to the nitrogen donor atom of the crown inhibits the charge-transfer process, leading to a cation-dependent enhancement of the LE emission and the fluorescence lifetimes by factors >10(3). This efficient "switching on" of the fluorescence renders the crowned BDP dye an extremely sensitive fluorescent probe for metal ions.

Item Type: Article
Uncontrolled Keywords: FUNCTIONALIZED 9-ARYLACRIDINIUM IONS; PHOTOPHYSICAL PROPERTIES; ELECTRON-TRANSFER; EXCITED-STATE; PARA-(9-ANTHRYL)-N,N-DIMETHYLANILINE DERIVATIVES; CROWNED MEROCYANINE; GLOBAL ANALYSIS; STEADY-STATE; PICOSECOND; SPECTROSCOPY
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Alumni or Retired Professors > Prof. Dr. Jörg Daub
Depositing User: Dr. Gernot Deinzer
Date Deposited: 14 Feb 2023 11:44
Last Modified: 14 Feb 2023 11:44
URI: https://pred.uni-regensburg.de/id/eprint/49264

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