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Paper des Monats
- ja (6)
Several series of crown fluoro-chromo-ionophores covering a broad spectral range are investigated experimentally and compared to their theoretically studied dimethylamino (DMA) analogues. It is shown that the logarithm of the complex stability constants log KS for NaI and CaII ions do not correlate with the observed complexation-induced shift. Likewise, an unsatisfactory correlation is found between the local charge density on the amino nitrogen of the DMA dyes and log KS. However, using the charge of the whole dimethylamino group instead strongly improves this correlation. This can be understood by considering pyramidalization and hyperconjugation effects on the amino nitrogen. The observed correlation allows a novel approach to the design of fluoroionophores with optimized properties.
Syntheses and photophysical properties of a series of cation-sensitive polymethine and styryl dyes
(2000)
The syntheses and photophysical properties of 20 cation-sensitive fluoroionophores carrying the tetraoxa monoaza 15-crown-5 receptor are described and discussed. Whereas complexation induces only weak effects for the positively charged hemicyanine probes, the closely related styryl dyes show stronger changes in their photophysical properties upon cation binding in the analytically advantageous near-infrared (NIR) region. The strongest effects in both cation-induced spectral effects and complex stability constants are observed for the uncharged probes of styryl base-type, but these probes usually absorb and emit at shorter wavelengths in the UV/VIS region. For both styryl dyes and styryl bases, in some cases cation-induced fluorescence enhancement or quenching is found.
The photophysical properties of several newly synthesized 1-benzothiazole-3-(4-donor)-phenyl-substituted prop-2-en-1-ones (substituted chalcones) are studied as a function of solvent polarity, temperature, and metal ion by employing steady-state and time-resolved spectroscopy. To investigate the effect of bulkiness and donor strength of the anilino moiety on the spectroscopic properties of these dyes, the spectroscopic behavior of the 4-N-dimethylamino (DMA), the 4-N-tetraoxa-monoaza-15-crown-5 (A15C5), and the 4-N-tetrathia-monoaza-15-crown-5 (AT415C5) derivatives as well as the 3-julolidino (Jul) analogue is compared. Absorption and fluorescence measurements reveal that the strength of the intramolecular charge transfer (ICT) process increases on the order of AT415C5 < A15C5 ~ DMA < Jul. The slight but significant differences between the two crowned dyes are well-supported by the results of the X-ray structure analysis, where oxa aza and thia aza crowns show essentially different geometries. For both fluoroionophores, this variation of heteroatom substitution pattern of the receptor induces specific cation selectivities. The spectroscopic effects accompanying complexation and the different binding sites are studied by steady-state and time-resolved optical spectroscopy as well as NMR spectroscopy. Whereas the probe carrying a tetraoxa monoaza 15-crown-5 receptor shows cation-induced fluorescence enhancement in the presence of alkali and alkaline-earth metal ions, its tetrathia analogue binds selectively to HgII, AgI, and CuII in acetonitrile. Moreover, an increase in fluorescence is observed for the latter probe even upon coordination to the widely known fluorescence quencher HgII. Besides receptor complexation, chelate formation in the benzothiazole-carbonyl acceptor part of these intrinsic fluorescent probes is possible, leading to a chromoionophoric signaling behavior in the near-infrared (NIR).
One of the key interests in the recent development of fluorescent molecular sensors and switches is the realization of systems that show strong signal changes as a response to the chemical trigger. Aiming at rational probe design, this article compiles and compares different promising strategies to extract those supramolecular and photophysical features that allow the construction of molecular devices suitable for efficient signaling. The examples comprise fluorescence OFFON as well as ONOFF operative systems and the mechanisms, properties, and limitations of the different design concepts are discussed.
A novel fluorescent host-guest material, molecular sieves of AlPO4-5-type doped with 2,2'-bipyridyl-3,3'-diol, was prepared and spectroscopically characterized. The composite crystals show a pronounced optical anisotropy, indicating a high degree of alignment of the guest molecules within the zeolitic pore system. A mean tilting angle of 22 was found for the orientation of the individual dye molecules in the straight channels. The corrected fluorescence emission spectra were determined, and time-resolved fluorescence studies revealed that the dye molecules are preferentially found in three different types of microenvironment. By invoking pH-dependent studies of the dye in aqueous solution, we could trace these spectroscopic features back to two main influences, coadsorbed water within AlPO4-5 pores and guest-host interactions with a few relatively weak Brnsted acid (defect) sites of the inorganic host network.
Two fluorescent dyes were incorporated into sol-gel derived SiO2 matrices. The dye was added to SiO2 precursors of different degrees of pre-condensation and the spectroscopic properties of the immobilized dye were measured at various aging and drying stages of the resulting gels. The significant influence of the processing parameters on the spectroscopic properties is manifested in the relative intensity of a second red shifted emission band (550560 nm), which was observed besides the typical coumarin emission band (495 nm). The appearance of this long wavelength emission might be attributed to dye aggregation or to other reactions with the ambient matrix forced by micro porosity phenomena.
The acceptor strength of the boron-dipyrromethene chromophore in directly linked donoracceptor compounds can be tuned by substituents in such a way that a fast excited state charge transfer takes place even for the comparatively weak benzo crown electron donor. This leads to strong fluorescence quenching. Upon binding of cations (Na+ and K+) to the benzo crown receptor, the donor properties of the latter are further reduced, partly suppressing charge transfer. Large fluorescence enhancement factors and cation-selective fluorescence decay times result which are the basis for improved analytical application of these dyes as highly sensitive fluorescent probes.