TY - JOUR A1 - Bricks, J. L. A1 - Slominskii, J. L. A1 - Kudinova, M. A. A1 - Tolmachev, A. I. A1 - Rurack, Knut A1 - Resch-Genger, Ute A1 - Rettig, W. T1 - Syntheses and photophysical properties of a series of cation-sensitive polymethine and styryl dyes N2 - 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. KW - Fluorescence KW - Ionophores KW - Unsymmetrical cyanines KW - Styryl dyes KW - Styryl bases PY - 2000 DO - https://doi.org/10.1016/S1010-6030(00)00208-2 SN - 1010-6030 SN - 1873-2666 VL - 132 IS - 3 SP - 193 EP - 208 PB - Elsevier CY - Lausanne AN - OPUS4-2089 LA - eng AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER - TY - JOUR A1 - Rurack, Knut A1 - Bricks, J. L. A1 - Reck, Günter A1 - Radeglia, Reiner A1 - Resch-Genger, Ute T1 - Chalcone-analogue dyes emitting in the near-infrared (NIR) - influence of donor-acceptor substitution and cation complexation on their spectroscopic properties and X-ray structure N2 - 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). PY - 2000 DO - https://doi.org/10.1021/jp994269k SN - 1089-5639 SN - 1520-5215 VL - 104 IS - 14 SP - 3087 EP - 3109 PB - Soc. CY - Washington, DC AN - OPUS4-2088 LA - eng AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER - TY - JOUR A1 - Rurack, Knut A1 - Resch-Genger, Ute A1 - Bricks, J.L. A1 - Spieles, Monika T1 - Cation-triggered 'switching on' of the red/near infra-red (NIR) fluorescence of rigid fluorophore-spacer-receptor ionophores PY - 2000 DO - https://doi.org/10.1039/b006430k SN - 0022-4936 SN - 0009-241x SN - 1359-7345 SN - 1364-548x IS - 21 SP - 2103 EP - 2104 PB - Royal Society of Chemistry CY - Cambridge AN - OPUS4-2087 LA - eng AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER -