TY - JOUR A1 - Trieflinger, C. A1 - Rurack, Knut A1 - Daub, J. T1 - "Turn ON/OFF your LOV light": Bordipyrromethen-Flavin-Dyaden als biomimetische, von der LOV-Domäne abgeleitete Schalter JF - Angewandte Chemie KW - Boron-dipyrromethene KW - Flavin KW - Thiol/disulfide KW - Fluorescence KW - Molecular switching KW - Photoreceptor mimicks PY - 2005 SN - 0044-8249 SN - 0932-2140 SN - 1521-3757 VL - 117 IS - 15 SP - 2328 EP - 2331 PB - Wiley-VCH CY - Weinheim AN - OPUS4-7305 LA - eng AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER - TY - JOUR A1 - Wu, D. A1 - Descalzo López, Ana Belén A1 - Weik, F. A1 - Emmerling, Franziska A1 - Shen, Z. A1 - You, X.-Z. A1 - Rurack, Knut T1 - A core-modified Rubyrin with meso-aryl substituents and phenanthrene-fused pyrrole rings: a highly conjugated near-infrared dye and Hg2+ probe JF - Angewandte Chemie / International Edition KW - Fluorescence KW - Mercury KW - NIR dyes KW - Porphyrinoids KW - Sensors PY - 2008 DO - https://doi.org/10.1002/Anie.200702854 SN - 1433-7851 SN - 1521-3773 SN - 0570-0833 VL - 47 IS - 1 SP - 193 EP - 197 PB - Wiley-VCH CY - Weinheim AN - OPUS4-16448 LA - eng AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER - TY - JOUR A1 - Climent Terol, Estela A1 - Biyikal, Mustafa A1 - Gawlitza, Kornelia A1 - Dropa, T. A1 - Urban, M. A1 - Costero, A. M. A1 - Martínez-Mánez, Ramon A1 - Rurack, Knut T1 - A rapid and sensitive strip-based quick test for nerve agents Tabun, Sarin, and Soman using BODIPY-modified silica materials JF - Chemistry - a European journal N2 - Test strips that in combination with a portable fluorescence reader or digital camera can rapidly and selectively detect chemical warfare agents (CWAs) such as Tabun (GA), Sarin (GB), and Soman (GD) and their simulants in the gas phase have been developed. The strips contain spots of a hybrid indicator material consisting of a fluorescent BODIPY indicator covalently anchored into the channels of mesoporous SBA silica microparticles. The fluorescence quenching response allows the sensitive detection of CWAs in the μg m−3 range in a few seconds. KW - Chemical warfare agents KW - Fluorescence KW - Hybrid sensor materials KW - Nerve gases KW - Test strip analysis PY - 2016 DO - https://doi.org/10.1002/chem.201601269 SN - 0947-6539 SN - 1521-3765 VL - 22 IS - 32 SP - 11138 EP - 11142 PB - Wiley CY - Online Library AN - OPUS4-37063 LA - eng AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER - TY - JOUR A1 - Leiterer, Jork A1 - Grabolle, Markus A1 - Rurack, Knut A1 - Resch-Genger, Ute A1 - Ziegler, J. A1 - Nann, T. A1 - Panne, Ulrich T1 - Acoustically Levitated Droplets - A Contactless Sampling Method for Fluorescence Studies JF - Annals of the New York academy of sciences N2 - Acoustic levitation is used as a newtool to study concentration-dependent processes influorescence spectroscopy. With this technique, small amounts of liquid and solid samples can be measured without the need for sample supports or containers, which often limits signal acquisition and can even alter sample properties due to interactions with the support material. We demonstrate that, because of the small sample volume, fluorescence measurements at high concentrations of an organic dye are possible without the limitation of inner-filter effects, which hamper such experiments in conventional, cuvette-based measurements. Furthermore, we show that acoustic levitation of liquid samples provides an experimentally simple way to study distance-dependent fluorescence modulations in semiconductor nanocrystals. The evaporation of the solvent during levitation leads to a continuous increase of solute concentration and can easily be monitored by laser-induced fluorescence. KW - Acoustic levitation KW - Dyes KW - Energy transfer KW - Fluorescence KW - Quantum dots KW - Nanocrystals KW - Ultrasonic trap PY - 2008 DO - https://doi.org/10.1196/annals.1430.039 SN - 0077-8923 SN - 1749-6632 SN - 0094-8500 VL - 1130 SP - 78 EP - 84 PB - New York Academy of Sciences CY - New York, NY AN - OPUS4-17658 LA - eng AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER - TY - JOUR A1 - Rurack, Knut A1 - Trieflinger, C. A1 - Kovalchuck, Anton V. A1 - Daub, J. T1 - An ionically driven molecular IMPLICATION gate operating in fluorescence Mode JF - Chemistry - A European journal N2 - An asymmetrically core-extended boron-dipyrromethene (BDP) dye was equipped with two electron-donating macrocyclic binding units with different metal ion preferences to operate as an ionically driven molecular IMPLICATION gate. A Na+-responsive tetraoxa-aza crown ether (R2) was integrated into the extended π system of the BDP chromophore to trigger strong intramolecular charge transfer (ICT2) fluorescence and guarantee cation-induced spectral shifts in absorption. A dithia-oxa-aza crown (R1) that responds to Ag+ was attached to the meso position of BDP in an electronically decoupled fashion to independently control a second ICT1 process of a quenching nature. The bifunctional molecule is designed in such a way that in the absence of both inputs, ICT1 does not compete with ICT2 and a high fluorescence output is obtained (InA=InB=0→Out=1). Accordingly, binding of only Ag+ at R1 (InA=1, InB=0) as well as complexation of both receptors (InA=InB=1) also yields Out=1. Only for the case in which Na+ is bound at R2 and R1 is in its free state does quenching occur, which is the distinguishing characteristic for the InA=0 and InB=1→Out=0 state that is required for a logic IMPLICATION gate and Boolean operations such as IF-THEN or NOT. KW - Charge transfer KW - Dyes/pigments KW - Fluorescence KW - Logic gates KW - Molecular devices PY - 2007 DO - https://doi.org/10.1002/chem.200700858 SN - 0947-6539 SN - 1521-3765 VL - 13 IS - 32 SP - 8998 EP - 9003 PB - Wiley-VCH Verl. CY - Weinheim AN - OPUS4-16085 LA - eng AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER - TY - JOUR A1 - Ashokkumar, Pichandi A1 - Bell, Jérémy A1 - Buurman, Merwe A1 - Rurack, Knut T1 - Analytical platform for sugar sensing in commercial beverages using a fluorescent BODIPY "light-up" probe JF - Sensors and Actuators B: Chemical N2 - Because of the globally increasing prevalence of diabetes, the need for accurate, efficient and at best miniaturized automated analytical systems for sugar detection in medical diagnostics and the food industry is still urgent. The development of molecular probes for sugars based on boronic acid receptors offers an excellent alternative to the kinetically slow enzyme-based sugar sensors. Moreover, by coupling such chelating units with dye scaffolds like BODIPYs (boron–dipyrromethenes), highly fluorescent sugar sensing schemes can be realized. In this work, a boronic acid-functionalized BODIPY probe was developed, which binds selectively to fructose’s adjacent diols to form cyclic boronate esters. Placement of an amino group in direct neighborhood of the boronic acid moiety allowed us to obtain a broad working range at neutral pH, which distinguishes the probe from the majority of systems working only at pH > 8, while still meeting the desired sensitivity in the micro-molar range due to a pronounced analyte-induced fluorescence increase. To enhance the applicability of the test in the sense described above, integration with a microfluidic chip was achieved. Here, fructose was selectively detected by fluorescence with similar sensitivity in real time on chip, and an assay for the straightforward detection of sugar in (colored) sodas without sample clean-up was established. KW - BODIPY dyes KW - Boronic acid KW - Fluorescence KW - Microfluidics KW - Sugars PY - 2018 DO - https://doi.org/10.1016/j.snb.2017.09.201 SN - 0925-4005 VL - 256 SP - 609 EP - 615 PB - Elsevier CY - Amsterdam AN - OPUS4-43102 LA - eng AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER - TY - JOUR A1 - Ros-Lis, J.V. A1 - Martínez-Mánez, Ramon A1 - Sancenón, F. A1 - Soto, J. A1 - Spieles, Monika A1 - Rurack, Knut T1 - Aquaraines as reporter units: insights into their photophysics, protonation, and metal-ion coordination behaviour JF - Chemistry - A European journal KW - Dyes/pigments KW - Fluorescence KW - Metal ions KW - Protonation KW - Squaraines KW - Farbstoffe KW - Fluoreszenz KW - Metallionen KW - Protonierung PY - 2008 DO - https://doi.org/10.1002/chem.200800300 SN - 0947-6539 SN - 1521-3765 VL - 14 SP - 10101 EP - 10114 PB - Wiley-VCH Verl. CY - Weinheim AN - OPUS4-18444 LA - eng AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER - TY - JOUR A1 - Shen, Z. A1 - Röhr, Holger A1 - Rurack, Knut A1 - Uno, H. A1 - Spieles, Monika A1 - Schulz, Burkhard A1 - Reck, Günter A1 - Ono, N. T1 - Boron-Diindomethene (BDI) Dyes and Their Tetrahydrobicyclo Precursors - en Route to a New Class of Highly Emissive Fluorophores for the Red Spectral Range JF - Chemistry - A European journal N2 - The X-ray crystallographic, optical spectroscopic, and electrochemical properties of a newly synthesized class of boron-diindomethene (BDI) dyes and their tetrahydrobicyclo precursors (bc-BDP) are presented. The BDI chromophore was designed to show intensive absorption and strong fluorescence in an applicationary advantageous spectral range. Its modular architecture permits fusion of a second subunit, for example, a receptor moiety to the dye's core to yield directly linked yet perpendicularly prearranged composite systems. The synthesis was developed to allow facile tuning of the chromophore platform and to thus adjust its redox properties. X-ray analysis revealed a pronounced planarity of the chromophore in the case of the BDIs, which led to a remarkable close packing in the crystal of the simplest derivative. On the other hand, deviation from planarity was found for the diester-substituted bc-BDP benzocrown that exhibits a butterfly-like conformation in the crystal. Both families of dyes show charge- or electron-transfer-type fluorescence-quenching characteristics in polar solvents when equipped with a strong donor in the meso-position of the core. These processes can be utilized for signaling purposes if an appropriate receptor is introduced. Further modification of the chromophore can invoke such a guest-responsive intramolecular quenching process, also for receptor groups of low electron density, for example, benzocrowns. In addition to the design of various prototype molecules, a promising fluoroionophore for Na+ was obtained that absorbs and emits in the 650 nm region and shows a strong fluorescence enhancement upon analyte binding. Furthermore, investigation of the remarkable solvatokinetic fluorescence properties of the butterfly-like bc-BDP derivatives suggested that a second intrinsic nonradiative deactivation channel can play a role in the photophysics of boron-dipyrromethene dyes. KW - Charge KW - Transfer KW - Dyes/pigments KW - Electron transfer KW - Fluorescence KW - Farbstoffe KW - Chemosensoren KW - NIR-Bereich KW - Photophysik KW - Röntgenstrukturanalyse PY - 2004 DO - https://doi.org/10.1002/chem.200400173 SN - 0947-6539 SN - 1521-3765 VL - 10 SP - 4853 EP - 4871 PB - Wiley-VCH Verl. CY - Weinheim AN - OPUS4-4125 LA - eng AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER - TY - CONF A1 - Rurack, Knut T1 - Bright Long-Wavelength Pyrrolic Dyes - Prospects for Applications in Fluorescence Sensing N2 - Since more than 20 years, optical spectroscopic techniques, in particular fluorescence-based methods, are on the rise in many different areas of chemical and biochemical analysis, with no end being in sight.1,2 Advances in miniaturization and remote applications on one hand and ground-breaking developments in microscopy and laser-based high-throughput instrumentation on the other hand have fuelled these developments substantially.3,4 At the core of utmost of these applications however is not only the instrument, but a small entity that is able to absorb and emit photons and thus to report on the actual (bio)chemistry that is going on in a particular sample of interest.5,6 Besides intense research on various types of luminescent particles (e.g., quantum dots and carbon dots) and proteins, dye chemistry has thus seen its revival and the number of publications dealing with the design, synthesis and application of new fluorescent dyes as probes, stains, labels or indicators is still continuing to grow. Among the various classes of dyes available as bright fluorophores for a wavelength range that is compatible with many (bio)analytical applications and the respective instrumentation, in particular pyrrolic dyes that do not belong to the classical porphyrins or phthalocyanines have received strong attention recently. Starting perhaps with the revival of the traditional boron-dipyrromethene laser dye ca. 15 years ago,7 these so-called BODIPYs have developed into a colourful spectrum of different derivatives.8 However, the interest in expanding the range of pyrrole-containing π-systems beyond BODIPYs has also constantly increased and has brought about several other pyrrole-based ring systems such as diketopyrrolopyrroles9 or dipyrrolonaphthyridinediones which possess a favourable brightness and other interesting properties. The present contribution will give a critical overview of the field, pinpointing advantages and prospects as well as discussing potential aspects of improvement with an emphasis on the chemical sensing and the longer wavelength range. T2 - Ninth International Conference on Porphyrins and Phthalocyanines CY - Nanjing, People's Republic of China DA - 03.07.2016 KW - Fluorescence KW - Dyes KW - Sensor KW - NIR KW - Pyrroles PY - 2016 AN - OPUS4-38796 LA - eng AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER - TY - JOUR A1 - Gawlitza, Kornelia A1 - Fischer, Tobias A1 - Rurack, Knut T1 - Chemical functionalization for quantitative spectroscopic labeling on macroscopically flat surfaces JF - Reference Module in Chemistry, Molecular Sciences and Chemical Engineering N2 - This chapter highlights the application of chemical derivatization (CD) to facilitate the quantification of surface functional groups being an important issue for a wide field of applications. The selective attachment of a chemical label to a surface functional group being afterwards exclusively detectable by a highly sensitive technique overcomes the problem of characterizing low amounts of functional groups on macroscopically flat surfaces. The most frequently employed methods include CD X-ray photoelectron spectroscopy, ultraviolet/visible absorption, and fluorescence spectroscopy, as well as time-of-flight secondary ion mass spectrometry. Herein, the basic conditions for the different techniques regarding the specific surface functional group which need to be quantified are discussed. Additionally, the substrate highly influences the compatibility of the corresponding method. Because not just the quantification but also the preparation of the desired application is important, a summary of different preparation methods for glass, polymer and gold substrates is presented. KW - Chemical derivatization KW - Fluorescence KW - Surface group quantification KW - Time-of-flight secondary ion mass spectrometry KW - UV/vis spectroscopy KW - X-ray photoelectron spectroscopy PY - 2018 SN - 978-0-12-409547-2 DO - https://doi.org/10.1016/B978-0-12-409547-2.13191-9 SP - 1 PB - Elsevier AN - OPUS4-43767 LA - eng AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER -