Non-native autoinducer analogs capable of modulating the SdiA quorum sensing receptor in Salmonella enterica serovar Typhimurium

• Matthew J. Styles and
• Helen E. Blackwell

Beilstein J. Org. Chem. 2018, 14, 2651–2664, doi:10.3762/bjoc.14.243

• identify an expanded range of synthetic ligands for SdiA. Herein, we report the screening of a focused library of AHL analogs for activity in the SdiA receptor from S. Typhimurium. Compound efficacies and potencies were measured in agonism and antagonism assays using an SdiA luminescence reporter system

• the positive control based on raw luminescence. Further, for the E. coli JLD271 reporter, the negative control was at 50% the level of the positive control; we reason that this higher background relative to S. Typhimurium is due to the overexpression of SdiA in this reporter. Conditions for both

• changing the expression of SdiA or by inhibiting the luminescence reporter. Conversely, the inability of F45 and 16 to even partially inhibit SdiA in the E. coli reporter system indicates that the means by which they inhibit SdiA activity in the S. Typhimurium reporter is dependent on either the expression

Synthesis of aryl sulfides via radical–radical cross coupling of electron-rich arenes using visible light photoredox catalysis

• Amrita Das,
• Mitasree Maity,
• Simon Malcherek,
• Burkhard König and
• Julia Rehbein

Beilstein J. Org. Chem. 2018, 14, 2520–2528, doi:10.3762/bjoc.14.228

• showed that an aryl disulfide could be cleaved by irradiation with visible light [49]. Some spectroscopic investigations (Figure 3) gave valuable information about the mechanism of the photoredox catalytic cycle. The luminescence intensity of [Ir(dF(CF3)ppy)2(dtbpy)]PF6 was quenched upon successive

• addition of 1,2,4-trimethoxybenzene (oxidation potential 1.02 V vs SCE, Figure 3a). The values are similar to the estimated excited state oxidation potential of [Ir(dF(CF3)ppy)2(dtbpy)]PF6 ( +1.21 V vs SCE in acetonitrile). On the other hand, the luminescence was quenched negligible on addition of diphenyl

• disulfide (Figure 3b). Stern–Volmer quenching studies showed that the arene is quenched at a much higher rate than the disulfide (Figure 3c). This indicates that the oxidation of the arene is the key step in the C–H sulfenylation reaction. Anisole does not quench the luminescence of [Ir(dF(CF3)ppy)2(dtbpy

Synthesis and photophysical studies of a multivalent photoreactive Ru^II-calix[4]arene complex bearing RGD-containing cyclopentapeptides

• Sofia Kajouj,
• Lionel Marcelis,
• Alice Mattiuzzi,
• Adrien Grassin,
• Damien Dufour,
• Pierre Van Antwerpen,
• Didier Boturyn,
• Eric Defrancq,
• Mathieu Surin,
• Julien De Winter,
• Pascal Gerbaux,
• Ivan Jabin and
• Cécile Moucheron

Beilstein J. Org. Chem. 2018, 14, 1758–1768, doi:10.3762/bjoc.14.150

• . Barton et al. demonstrated in 1990 that [Ru(bpy)2(dppz)]2+ behaves as a light-switch for DNA [5]: this complex is not luminescent in water but upon intercalation within the DNA base pairs stack, the complex luminescence is restored. Derivatives of [Ru(bpy)2(dppz)]2+ and complexes bearing similar aromatic

• luminescence lifetime and determined the quantum yield of luminescence under air and argon atmosphere for conjugate 9 and reference [Ru(TAP)2phen]2+ in water with 5% DMSO in order to avoid any formation of aggregates. The data gathered in Table 1 clearly indicate that the tethering of the [Ru(TAP)2phen]2

• cyclic pentapeptide units c-[RGDfK] 8 (see Supporting Information File 1). No modification of the luminescence by intermolecular quenching was observed, confirming the absence of internal quenching in the conjugate 9. Photoreactivity of RuII-calixarene conjugate 9 The photoreactivity of Ru-TAP complexes

Recent advances in phosphorescent platinum complexes for organic light-emitting diodes

• Cristina Cebrián and
• Matteo Mauro

Beilstein J. Org. Chem. 2018, 14, 1459–1481, doi:10.3762/bjoc.14.124

• chemical structure is sketched in Figure 9 [41]. Depending on the π-conjugation of the NHC-based bidentate ligand, emitting complexes with luminescence varying from blue (19 and 20) to yellow (21) were obtained. Several devices were prepared following a remote phosphor configuration, which places the

• nonradiative deactivation channels [25][44]. Nevertheless, the use of multidentate chromophoric ligands that are able to provide metal–ligand bonds with higher covalent character, as for instance cyclometalating ligands, has proven to be a successful strategy for improving the luminescence properties due to

• , together with the use of heterocyclic moieties such as thiophene or carbazole, clearly favours the luminescence properties of these type of platinum(II) complexes [68]. As aforementioned, N-deprotonable azole units constitute a compelling alternative to C-cyclometalating ligands [16]. In this regard

D–A–D-type orange-light emitting thermally activated delayed fluorescence (TADF) materials based on a fluorenone unit: simulation, photoluminescence and electroluminescence studies

• Lin Gan,
• Xianglong Li,
• Xinyi Cai,
• Kunkun Liu,
• Wei Li and
• Shi-Jian Su

Beilstein J. Org. Chem. 2018, 14, 672–681, doi:10.3762/bjoc.14.55

• one peak at 593 nm was observed for the dilute toluene solutions of both molecules with the typical PL spectra from the radiative transition of ICT states, which could be the evidence of the existence of strong ICT states of both molecules. More importantly, both materials achieve orange luminescence

• . PLQY measurements of 1:CBP and 2:CBP are 7% and 26%, respectively. The PLQY measurements of the doped films with lower concentration show varying degrees of deviation due to the incomplete energy transfer and the obvious luminescence from CBP (PLQY of 1 and 2 doped in CBP with 1 wt % are 2% and 10

• is a promising acceptor for orange TADF materials, which aids in the design of the TADF behavior and luminescence color of 1 and 2. Owing to the strong electron-withdrawing ability and extended conjugation length of fluorenone unit, the emission peaks of both materials show obvious red-shifts from

Investigating radical cation chain processes in the electrocatalytic Diels–Alder reaction

• Yasushi Imada,
• Yohei Okada and
• Kazuhiro Chiba

Beilstein J. Org. Chem. 2018, 14, 642–647, doi:10.3762/bjoc.14.51

• luminescence quenching experiments [19]. With such an understanding in hand, radical ion chain processes could be further optimized to realize greener transformations. We have been developing anodic cycloadditions [20][21][22][23][24][25] enabled by lithium perchlorate/nitromethane electrolyte solution [26

Recent advances on organic blue thermally activated delayed fluorescence (TADF) emitters for organic light-emitting diodes (OLEDs)

• Thanh-Tuân Bui,
• Fabrice Goubard,
• Malika Ibrahim-Ouali,
• Didier Gigmes and
• Frédéric Dumur

Beilstein J. Org. Chem. 2018, 14, 282–308, doi:10.3762/bjoc.14.18

• reducing the global energy demand on Earth, two parameters govern the power consumption of OLEDs, namely the quantum yield of luminescence of the light emitting material and the device stacking. Indeed, the driving voltage of OLEDs is highly sensitive to the thickness of the different layers, the charge

• delayed fluorescence (TADF) emitters. As specificity, these materials can thermally repopulate the singlet state from the triplet state by reverse intersystem crossing (RISC), leading to an increase of the luminescence intensity. From the OLEDs viewpoint, TADF emitters behave by harvesting both singlet

• . The decay time of the delayed component of luminescence was determined as being 2.36 μs and 6.71 μs for B1 and B2, respectively. When evaluated in multilayered OLEDs, a blue electroluminescence (EL) peaking at 466 nm and 479 nm, an external quantum efficiency (EQE) of 15.1% and 16.0% were obtained for

Polarization spectroscopy methods in the determination of interactions of small molecules with nucleic acids – tutorial

• Tamara Šmidlehner,
• Ivo Piantanida and
• Gennaro Pescitelli

Beilstein J. Org. Chem. 2018, 14, 84–105, doi:10.3762/bjoc.14.5

• , which is ideal for the selective study of DNA ligands that strongly change fluorescence upon binding [3]. In a sense complementary to FDCD, also circularly polarized luminescence (CPL) is a chiroptical emission technique which has been employed in the same context for the first time recently [12]. The

Pyrene–nucleobase conjugates: synthesis, oligonucleotide binding and confocal bioimaging studies

• Artur Jabłoński,
• Yannic Fritz,
• Hans-Achim Wagenknecht,
• Rafał Czerwieniec,
• Tytus Bernaś,
• Damian Trzybiński,
• Krzysztof Woźniak and
• Konrad Kowalski

Beilstein J. Org. Chem. 2017, 13, 2521–2534, doi:10.3762/bjoc.13.249

• . Confocal microscopy confirmed that 5 predominantly stains mitochondria but it also accumulates in the nucleoli of the cells. Keywords: confocal microscopy; luminescence; nucleobases; oligonucleotide binding; pyrene; X-ray; Introduction Pyrene is a planar, polycyclic aromatic hydrocarbon which shows well

• geometry, ten excitations, five without spin flip and five to triplet excited states, respectively, were computed. The results for luminescence relevant transitions are summarized in Table 2. The TD-DFT computations predict, in particular, that the fluorescent state S1 of hydroxy compound 5 with the

• determined by Analytical Services of the Polish Academy of the Sciences, Łódź. Experimental details Luminescence measurements UV–vis absorption spectra were recorded with a Varian Cary 300 double beam spectrometer. Luminescence spectra were measured for air-saturated and degassed diluted (c ≈ 5·10–5 M

Exploring mechanochemistry to turn organic bio-relevant molecules into metal-organic frameworks: a short review

• Vânia André,
• Sílvia Quaresma,
• João Luís Ferreira da Silva and
• M. Teresa Duarte

Beilstein J. Org. Chem. 2017, 13, 2416–2427, doi:10.3762/bjoc.13.239

• and materials sciences, including organic solids [2] with pharmaceutical, luminescence- and thermoactive properties; studies of biomolecular recognition, asymmetric catalysis, interlocked systems and racemic resolution [2]. More recently mechanochemical methods were again successfully applied to the

• ], luminescence [67], non-linear optics [68] and magnetism [69], as well as contrast agents for magnetic resonance imaging (MRI) [70] and as drug carriers in systems for controlled drug delivery and release [64][71][72][73][74][75][76][77][78][79][80]. Also under development are new systems with potential use in

• water at approximately 80 °C and melt/decompose above 200–250 °C [124]. This type of BioMOFs enclosing lanthanides and cations with potential luminescence properties can be explored for theranostic applications. Figure 1 shows some examples of the networks obtained. Braga et al. synthesized new BioMOFs

Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole

• Martina Tireli,
• Silvija Maračić,
• Stipe Lukin,
• Marina Juribašić Kulcsár,
• Dijana Žilić,
• Mario Cetina,
• Ivan Halasz,
• Silvana Raić-Malić and
• Krunoslav Užarević

Beilstein J. Org. Chem. 2017, 13, 2352–2363, doi:10.3762/bjoc.13.232

• Raman monitoring of formation of the triazole 5 using copper(II) acetate monohydrate (5 mol %, method 2a) revealed strong luminescence of the reaction mixture indicating the direct involvement of the catalyst in the milling process and the formation of luminescent copper species, which hindered a

• detected. The luminescence of the reaction mixture gradually changed during milling and the final spectrum after 213 minutes milling exhibited a single luminescent maximum centered at around 1500 cm−1 (Figure 2a) possibly due the formation of different copper complexes as milling progressed. Milling by

• method 2b, where the catalyst CuI was added in concentrations of 2 mol %, showed strong luminescence similar to the one observed in milling by method 2a, starting after ca. 3 minutes milling and covering most of Raman signals already after 10 minutes milling. In this case, however, luminescence grew

One-pot syntheses of blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones by T3P^® activation of 3-arylpropiolic acids

• Melanie Denißen,
• Alexander Kraus,
• Guido J. Reiss and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2017, 13, 2340–2351, doi:10.3762/bjoc.13.231

• one-pot process. Here, we report the development of the one-pot synthesis of these title compounds by a consecutive pseudo three-component approach and the investigation of the luminescence behavior by absorption and emission spectroscopy. Results and Discussion Synthesis and structure of 4

Phosphonic acid: preparation and applications

• Charlotte M. Sevrain,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2017, 13, 2186–2213, doi:10.3762/bjoc.13.219

• ) [69] or layered simple hydroxide (LSH) [70]. These materials prepared from phosphonic acids were assessed for numerus applications, including nuclear fuel stewardship and separations of actinides [71], porosity [72][73][74], bactericidal properties [75], inorganic salt release [76], luminescence [77

New electroactive asymmetrical chalcones and therefrom derived 2-amino- / 2-(1H-pyrrol-1-yl)pyrimidines, containing an N-[ω-(4-methoxyphenoxy)alkyl]carbazole fragment: synthesis, optical and electrochemical properties

• Daria G. Selivanova,
• Alexei A. Gorbunov,
• Olga A. Mayorova,
• Alexander N. Vasyanin,
• Igor V. Lunegov,
• Elena V. Shklyaeva and
• Georgii G. Abashev

Beilstein J. Org. Chem. 2017, 13, 1583–1595, doi:10.3762/bjoc.13.158

• causes the formation of excimers, which degrades the quality of the blue luminescence. On the other hand, the interaction of bulky side chains with each other can intensify an undesirable charge transfer in thin polymer films that can be overcome by introducing of terminal aromatic moieties into the

• colourless (2a,b) to orange (7a,b). Under UV irradiation (λeх = 315–390 nm) the luminescence of solutions varies from blue (2a,b) to orange (7a,b). It has been found out that UV-irradiated solutions of the obtained chromophores 6a,b–8a,b change their colours in different solvents of various polarity; for

Energy down converting organic fluorophore functionalized mesoporous silica hybrids for monolith-coated light emitting diodes

• Markus Börgardts and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2017, 13, 768–778, doi:10.3762/bjoc.13.76

• employing of inorganic luminophores. Further optimization of the dye loadings of these monoliths as well as fine tuning of the correlated color temperatures and determination of their luminescence efficiencies is currently under way. Additionally, studies on the photostability of the hybrid materials are in

Novel β-cyclodextrin–eosin conjugates

• Gábor Benkovics,
• Damien Afonso,
• András Darcsi,
• Szabolcs Béni,
• Sabrina Conoci,
• Éva Fenyvesi,
• Lajos Szente,
• Milo Malanga and
• Salvatore Sortino

Beilstein J. Org. Chem. 2017, 13, 543–551, doi:10.3762/bjoc.13.52

• window [30]. As shown in Figure 8, excitation of the conjugate 2–β-CD with visible green light generates the characteristic luminescence signals with a maximum at ca. 1270 nm analogously to what observed for free dye 2. We obtained a 1O2 quantum yield ΦΔ = 0.47, that is very similar to that of the free

• fluorescence observed for aqueous solutions of (a) eosin Y (2) and (b) the 2–β-CD conjugate. λexc = 455 nm; λem = 570 nm. 1O2 luminescence detected upon 528 nm light excitation of D2O solutions of (a) eosin Y (2) and (b) 2–β-CD conjugate having the same absorbance at the excitation wavelength. Supporting

Synthesis of 1-indanones with a broad range of biological activity

• Marika Turek,
• Dorota Szczęsna,
• Marek Koprowski and
• Piotr Bałczewski

Beilstein J. Org. Chem. 2017, 13, 451–494, doi:10.3762/bjoc.13.48

• anhydrides which cyclized to produce cyclic ketones. In order to complete the catalytic cycle, Nafion®-H was regenerated in the acylation step. Investigation of luminescence is a source of valuable information in modern molecular biology, immunology and embryology. An example of a bioluminescent molecule is

• obtained from the reaction of o-phthalaldehyde (86) with acetophenone 87 (Scheme 28). Iron(III) complexes of 88a–d turned out to be promising candidates for potential photovoltaic or luminescence applications. An intramolecular hydroacylation, catalyzed by nickel(0)/N-heterocyclic carbenes leading to the

Synthesis and optical properties of new 5'-aryl-substituted 2,5-bis(3-decyl-2,2'-bithiophen-5-yl)-1,3,4-oxadiazoles

• Anastasia S. Kostyuchenko,
• Tatyana Yu. Zheleznova,
• Anton J. Stasyuk,
• Aleksandra Kurowska,
• Wojciech Domagala,
• Adam Pron and
• Alexander S. Fisyuk

Beilstein J. Org. Chem. 2017, 13, 313–322, doi:10.3762/bjoc.13.34

• by quantum chemical DFT/TDDFT calculations carried out for these new molecules. Keywords: bithiophene; donor–acceptor; luminescence; 1,3,4-oxadiazole; palladium-catalyzed coupling; Introduction π-Conjugated donor–acceptor (D-A) compounds are of significant scientific interest because they

Supramolecular frameworks based on [60]fullerene hexakisadducts

• Andreas Kraft,
• Johannes Stangl,
• Ana-Maria Krause,
• Klaus Müller-Buschbaum and
• Florian Beuerle

Beilstein J. Org. Chem. 2017, 13, 1–9, doi:10.3762/bjoc.13.1

• materials with the prospect of applications in gas storage [2][3], catalysis [4][5], luminescence [6][7][8][9] and sensing [10][11][12][13] or optoelectronics [14][15][16]. Owing to a modular approach, building blocks and cross-linking interactions can be varied over a wide range resulting in metal-organic

Inhibition of peptide aggregation by means of enzymatic phosphorylation

• Kristin Folmert,
• Malgorzata Broncel,
• Hans v. Berlepsch,
• Christopher H. Ullrich,
• Mary-Ann Siegert and
• Beate Koksch

Beilstein J. Org. Chem. 2016, 12, 2462–2470, doi:10.3762/bjoc.12.240

• T fluorescence spectroscopy Fluorescence spectra were recorded by using a 1 cm path length quartz cuvette (Hellma, Müllheim, Germany) and a luminescence spectrometer LS50B (Perkin-Elmer, Boston, MA, USA). Spectra were recorded at room temperature from 470−500 nm after excitation at 450 nm

Thiophene-forming one-pot synthesis of three thienyl-bridged oligophenothiazines and their electronic properties

• Dominik Urselmann,
• Konstantin Deilhof,
• Bernhard Mayer and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2016, 12, 2055–2064, doi:10.3762/bjoc.12.194

• [53][54][55] substituted (oligo)phenothiazines. Their pronounced reversible oxidation potentials, their electro- and photochromicity [56], and their luminescence [57][58] have rendered (oligo)phenothiazines interesting candidates as donors in donor–acceptor conjugates with photo-induced electron

Mutagenic activity of quaternary ammonium salt derivatives of carbohydrates

• Barbara Dmochowska,
• Karol Sikora,
• Anna Woziwodzka,
• Jacek Piosik and
• Beata Podgórska

Beilstein J. Org. Chem. 2016, 12, 1434–1439, doi:10.3762/bjoc.12.138

• using two different techniques: The Vibrio harveyi luminescence assay and the Ames test. The obtained results support previous findings contesting QAS safety and indicate that QAS, specifically pyridinium derivatives, might be mutagenic. Keywords: 6-bromohexyl D-glucopyranoside; microbiological

• the Vibrio luminescence assay at all. Apart from N-[6-(β-D-glucopyranosyloxy)hexyl]-N,N,N-trimethylammonium bromide (5a), pyridinium salts tend to be more mutagenic than their trimethylammonium counterparts. Moreover, the position of the hexyl chain occurs to be important for mutagenicity of

• (marked in black), positive control (6-chloro-9-[3-(2-chloroethylamino)propylamino]-2-methoxyacridine dihydrochloride /ICR191/, 100 nM). Bars indicate mean values (± standard deviation) of bacterial luminescence, expressed as relative light units (RLU) per A575 of bacterial culture. Luminescence of the

Biradical vs singlet oxygen photogeneration in suprofen–cholesterol systems

• Fabrizio Palumbo,
• Francisco Bosca,
• Isabel M. Morera,
• Inmaculada Andreu and
• Miguel A. Miranda

Beilstein J. Org. Chem. 2016, 12, 1196–1202, doi:10.3762/bjoc.12.115

• luminescence at 1270 nm, using a germanium diode as detector. The singlet oxygen lifetime (Figure 7A) was found to be ca. 70 μs in all cases (in agreement with the1O2 lifetime reported in the literature [20] for the same solvent). The photosensitized singlet oxygen production was established with a quantum

• , 130.8, 134.9, 140.1, 147.0, 156.0, 172.9; HRMS–EI (m/z): [M – H]+ calcd for C41H55O3S, 627.3866; found, 627.3846. Singlet oxygen measurements As described in [13], the luminescence (1270 nm) from singlet oxygen was detected by means of an Oriel 71614 germanium photodiode (5 mm2) coupled to the laser

Bright molecules for sensing, computing and imaging: a tale of two once-troubled cities

• A. Prasanna de Silva

Beilstein J. Org. Chem. 2015, 11, 2774–2784, doi:10.3762/bjoc.11.298

• advantages of predictive behaviour which is rare in chemical contexts. Since an electron trying to leave a receptor would be electrostatically held back by a cation held there, it was clear that PET processes could be switched ‘off’ by an externally impressed chemical command. Since PET and luminescence

• compete for the deactivation of the same excited state, it was equally clear that a luminescence signal could be switched ‘on’ by chemical command. Therefore, we were fortunate to be able to introduce a general design tool of luminescent PET sensing/switching [11][12][13][14][15], which even handled

• possible information processors [56]. Then it dawned on me that the 'lumophore–spacer–receptor’ system could be elaborated into Boolean logic devices with chemical inputs and luminescence output. The first device, which initiated molecular logic-based computation as an experimental field, arose in the form

Recent advances in metathesis-derived polymers containing transition metals in the side chain

• Ileana Dragutan,
• Valerian Dragutan,
• Bogdan C. Simionescu,
• Albert Demonceau and
• Helmut Fischer

Beilstein J. Org. Chem. 2015, 11, 2747–2762, doi:10.3762/bjoc.11.296

• between the metal and the organic polymer backbone and/or side chains is crucial for ensuring the desired properties for the hybrid material [68]. Indeed, when appraising luminescence of a series of polynorbornenes attaching various homoleptic bi- or trinuclear lanthanide salen complexes (with La, Nd, Yb