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

Synthesis and photophysical characteristics of polyfluorene polyrotaxanes

• Aurica Farcas,
• Giulia Tregnago,
• Ana-Maria Resmerita,
• Pierre-Henri Aubert and
• Franco Cacialli

Beilstein J. Org. Chem. 2015, 11, 2677–2688, doi:10.3762/bjoc.11.288

• lifetime τ = 0.7 ns and 0.8 ns, whereas the 3·TM-γCD polyrotaxane shows a bi-exponential decay consisting of a main component (with a weight of 98% of the total luminescence) with a relatively short decay constant of τ1 = 0.7 ns and a minor component with a longer lifetime of τ2 = 5.4 ns (2%). The

• weights of 98 and 2%, respectively. The longer τ for the 3·TM-γCD polyrotaxane is consistent with “interchain states”. While these do not dominate the luminescence of the materials (the longer lifetime only accounts for 2% of the total PL weight), they are plausible, considered the significantly bigger

2-Hetaryl-1,3-tropolones based on five-membered nitrogen heterocycles: synthesis, structure and properties

• Yury A. Sayapin,
• Inna O. Tupaeva,
• Alexandra A. Kolodina,
• Eugeny A. Gusakov,
• Vitaly N. Komissarov,
• Igor V. Dorogan,
• Nadezhda I. Makarova,
• Anatoly V. Metelitsa,
• Valery V. Tkachev,
• Sergey M. Aldoshin and
• Vladimir I. Minkin

Beilstein J. Org. Chem. 2015, 11, 2179–2188, doi:10.3762/bjoc.11.236

• manifested in the batochromic (Δλ = 15–19 nm) shift of the longest wavelength absorption band as compared with the parent 2-(2-hydroxyphenyl)benzoxazole (cyclohexane, λmax = 321, 334 nm [35]). The excitation spectra of ASS-luminescence correspond to the absorption spectra of the hydroxy form of compounds 11a

Selected synthetic strategies to cyclophanes

• Sambasivarao Kotha,
• Mukesh E. Shirbhate and
• Gopalkrushna T. Waghule

Beilstein J. Org. Chem. 2015, 11, 1274–1331, doi:10.3762/bjoc.11.142

• macrocycles. These molecules show excellent chiroptical properties such as high fluorescence quantum efficiency and a large circularly polarized luminescence dissymmetry factor. Cyclophanes are carbon-rich materials containing extensive alkyne moieties with a persistent molecular architecture. Orita and co

Properties of PTFE tape as a semipermeable membrane in fluorous reactions

• Brendon A. Parsons,
• Olivia Lin Smith,
• Myeong Chae and
• Veljko Dragojlovic

Beilstein J. Org. Chem. 2015, 11, 980–993, doi:10.3762/bjoc.11.110

• reaction was directional. Only the oxalate–rubrene solution exhibited luminescence during the reaction, regardless of whether it was in the delivery tube or the vial (Figure 11). The peroxide solution remained dark. The reactions with the aqueous peroxide solution proceeded with no change in the column

Synthesis and chemosensing properties of cinnoline-containing poly(arylene ethynylene)s

• Natalia A. Danilkina,
• Petr S. Vlasov,
• Semen M. Vodianik,
• Andrey A. Kruchinin,
• Yuri G. Vlasov and
• Irina A. Balova

Beilstein J. Org. Chem. 2015, 11, 373–384, doi:10.3762/bjoc.11.43

• Optical sensors provide an efficient and sensitive approach for the rapid detection and identification of a wide range of chemical substrates by measuring the changes of optical properties such as absorbance, reflectance, luminescence, or fluorescence [1]. Among them a type of sensors based on conjugated

Conjugates of methylated cyclodextrin derivatives and hydroxyethyl starch (HES): Synthesis, cytotoxicity and inclusion of anaesthetic actives

• Lisa Markenstein,
• Antje Appelt-Menzel,
• Marco Metzger and
• Gerhard Wenz

Beilstein J. Org. Chem. 2014, 10, 3087–3096, doi:10.3762/bjoc.10.325

• generation of a luminescent signal proportional to the amount of ATP present, which is directly proportional to the number of cells in culture. The luminescence signal was measured in a plate reader (infinite M200, TECAN, Männedorf, Swizerland). 5a and DIMEB were each solved in standard basal medium (MEM) or

• luminescence was measured after 2 min of shaking and 10 min incubation at room temperature in the TECAN plate reader. All results presented are based on at least three independent biological tests. Statistical significance was determined by analysis of variance and p < 0.05. Materials: Hydroxyethyl starch (HES

Synthesis and properties of novel star-shaped oligofluorene conjugated systems with BODIPY cores

• Clara Orofino-Pena,
• Diego Cortizo-Lacalle,
• Joseph Cameron,
• Muhammad T. Sajjad,
• Pavlos P. Manousiadis,
• Neil J. Findlay,
• Alexander L. Kanibolotsky,
• Dimali Amarasinghe,
• Peter J. Skabara,
• Tell Tuttle,
• Graham A. Turnbull and
• Ifor D. W. Samuel

Beilstein J. Org. Chem. 2014, 10, 2704–2714, doi:10.3762/bjoc.10.285

• ,4a-diaza-s-indacene unit has attracted much attention due to the properties it imparts to the compounds that contain it, such as efficient luminescence, high absorptivity, good photostability and solubility in common solvents [1][2][3][4]. Due to these properties, BODIPY-containing conjugated systems

• lowers the luminescence efficiency of the material. Due to this aggregation and a low Stokes shift, BODIPY dyes with efficient emission in the solid state are still rare [16]. One of the strategies to suppress the aggregation of π-functional emissive units is to incorporate them into star-shaped

A small azide-modified thiazole-based reporter molecule for fluorescence and mass spectrometric detection

• Stefanie Wolfram,
• Hendryk Würfel,
• Stefanie H. Habenicht,
• Christine Lembke,
• Phillipp Richter,
• Eckhard Birckner,
• Rainer Beckert and
• Georg Pohnert

Beilstein J. Org. Chem. 2014, 10, 2470–2479, doi:10.3762/bjoc.10.258

• samples in aqueous solution. Ideally a pH-independent fluorescence should guarantee for unbiased detection in tissues or under variable analytical conditions. In the light of our detailed knowledge of luminescence properties of pyridylthiazoles we considered this compound class to be ideally suited for

• , USA) in combination with a Luminescence Spectrophotometer LS 50 (Perkin Elmer, Waltham, MA, USA). For DNS (8) and NBD (9) emission maxima were obtained with a FP-6500 (Jasco, Tokyo, Japan) spectrofluorimeter. LC–ESIMS and UV–vis detection For LC–MS measurements we used an Acquity™ Ultraperformance LC

The effect of permodified cyclodextrins encapsulation on the photophysical properties of a polyfluorene with randomly distributed electron-donor and rotaxane electron-acceptor units

• Aurica Farcas,
• Ana-Maria Resmerita,
• Pierre-Henri Aubert,
• Flavian Farcas,
• Iuliana Stoica and
• Anton Airinei

Beilstein J. Org. Chem. 2014, 10, 2145–2156, doi:10.3762/bjoc.10.222

• “insulation” of the individual molecular wires. Moreover, recently reported results have shown improvements of the thermal stability, solubility, luminescence and surface characteristics of polyrotaxanes compared to those of non-rotaxane counterparts [8][13][19][20][21][22][23][24][25]. This approach has also

Synthesis of new, highly luminescent bis(2,2’-bithiophen-5-yl) substituted 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole

• Anastasia S. Kostyuchenko,
• Vyacheslav L.Yurpalov,
• Aleksandra Kurowska,
• Wojciech Domagala,
• Adam Pron and
• Alexander S. Fisyuk

Beilstein J. Org. Chem. 2014, 10, 1596–1602, doi:10.3762/bjoc.10.165

• functionalised oligothiophenes, coupled to other heteroaromatic cores. Keywords: bithiophene; donor–acceptor; luminescence; 1,3,4-oxadiazole; 1,3,4-thiadiazole; 4H-1,2,4-triazole; Introduction In the past two decades oligo- and polythiophenes gained a significant research interest due to their wide application

• ][12][13][14][15], oxadiazole [14][15][16][17] or tetrazine units [13][18][19][20] have been reported. Moreover, luminescence properties of these derivatives are superior to those of the corresponding penta-ring oligothiophenes. For example, the central heterocycle ring replacement in substituted

Pyrene-modified PNAs: Stacking interactions and selective excimer emission in PNA₂DNA triplexes

• Alex Manicardi,
• Lucia Guidi,
• Alice Ghidini and
• Roberto Corradini

Beilstein J. Org. Chem. 2014, 10, 1495–1503, doi:10.3762/bjoc.10.154

• maximum of the first derivative of the melting curves. Fluorescence measurements. Fluorescence spectra were recorded on a Perkin Elmer LS55 luminescence spectrometer equipped with a LAUDA ECOline RE104 temperature control system, exciting at 347 nm (slit: 5.0 nm), scanning from 370 nm to 550 nm, a scan

Palladium-catalysed cross-coupling reaction of ultra-stabilised 2-aryl-1,3-dihydro-1H-benzo[d]1,3,2-diazaborole compounds with aryl bromides: A direct protocol for the preparation of unsymmetrical biaryls

• Siphamandla Sithebe and
• Ross S. Robinson

Beilstein J. Org. Chem. 2014, 10, 1107–1113, doi:10.3762/bjoc.10.109

• π-conjugated organic molecules containing a three-coordinate boron moiety such as trimesitylborane (4), arylalkynyldimesitylborane 5 and 2-aryl-1,3-diethyl-1H-benzo[d]1,3,2-diazaborole 6 (Figure 2) are well known and have received considerable attention due to their interesting luminescence

The Ugi four-component reaction as a concise modular synthetic tool for photo-induced electron transfer donor-anthraquinone dyads

• Sarah Bay,
• Gamall Makhloufi,
• Christoph Janiak and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2014, 10, 1006–1016, doi:10.3762/bjoc.10.100

• . These novel donor–acceptor dyads are electronically decoupled in the electronic ground state according to UV–vis spectroscopy and cyclic voltammetry. However, in the excited state the inherent donor luminescence is efficiently quenched. Previously performed femtosecond spectroscopic measurements account

Metal and metal-free photocatalysts: mechanistic approach and application as photoinitiators of photopolymerization

• Jacques Lalevée,
• Sofia Telitel,
• Pu Xiao,
• Marc Lepeltier,
• Frédéric Dumur,
• Fabrice Morlet-Savary,
• Didier Gigmes and
• Jean-Pierre Fouassier

Beilstein J. Org. Chem. 2014, 10, 863–876, doi:10.3762/bjoc.10.83

• -trapping, laser flash photolysis, steady state photolysis, cyclic voltammetry and luminescence experiments. Keywords: LEDs; photoinitiators; photopolymerization; photoredox catalysis; Introduction Photoredox catalysis is now well-known and largely used in organic synthesis, especially in the development

• /luminescence experiments (Figure 7B). From these data, a favorable 3Ir(piq)2(tmd)/Ph2I+ oxidation process can be expected, i.e., the free energy change ΔG for the corresponding electron transfer is negative (ΔG = −1.2 eV as calculated from the classical Rehm–Weller ΔG = Eox – Ered – ET + C where Eox, Ered, ET

• polymerized through a photoredox catalysis approach. The new proposed PIC (Ir(piq)2(tmd)). UV–visible light absorption spectra for Ir(piq)2(tmd) (2) and Ir(ppy)3 (1); solvent: acetonitrile. (A) cyclic voltamogramm for Ir(piq)2(tmd) in acetonitrile; (B) absorption (a) and luminescence (b) spectra for Ir(piq)2

Rapid pseudo five-component synthesis of intensively blue luminescent 2,5-di(hetero)arylfurans via a Sonogashira–Glaser cyclization sequence

• Fabian Klukas,
• Alexander Grunwald,
• Franziska Menschel and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2014, 10, 672–679, doi:10.3762/bjoc.10.60

• interesting due to their bright blue luminescence with remarkably high quantum yields. The electronic structure of the title compounds is additionally studied with DFT computations. Keywords: C–C coupling; copper; DFT; fluorescence; furans; mircowave-assisted synthesis; multicomponent reactions; palladium

• 2,5-diphenylfuran (2a, Table 1) starting from 1,4-diphenylbutadiyne (1a) as a substrate. Just upon eyesight a remarkable luminescence of 2a caught our attention and we were encouraged to perform photophysical studies with these products as well (vide infra). In a set of experiments the reaction times

• in a one-pot fashion, which opens a ready access to biologically active furan derivatives. In addition the investigation of the photophysical properties of these compounds reveals an intense blue luminescence in solution approaching unity for the fluorescence quantum yield Φf of distinct derivatives

One-pot three-component synthesis and photophysical characteristics of novel triene merocyanines

• Christian Muschelknautz,
• Robin Visse,
• Jan Nordmann and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2014, 10, 599–612, doi:10.3762/bjoc.10.51

• recorded in dichloromethane solution and of thin films prepared by dropcasting of concentrated dichloromethane solutions on glass-probe cuvettes (Table 4). For the powders and films of the merocyanines 8 intense deep-red luminescence was detected upon eyesight. The emission spectra of the films of 8 were

• responsible for the intense longest-wavelength absorption band upon optical excitation (Figure 4). In contrast to the deep-red luminescence of both amorphous films and dyes in the solid state with sharp bands between 644 and 665 nm (Figure 5), the emission in solution is completely quenched. As already

• formation of the corresponding 4-(3-methylbenzo[d]thiazol-2(3H)-ylidene)but-2-en-1-ylideneindolone. 4-(1,3,3-Trimethylindolin-2-ylidene)but-2-en-1-ylideneindolones are also the exclusive products for N-tosylanilides as starting materials. As a result of aggregation-induced luminescence, 1-styryleth-2

Physalin H from Solanum nigrum as an Hh signaling inhibitor blocks GLI1–DNA-complex formation

• Midori A. Arai,
• Kyoko Uchida,
• Samir K. Sadhu,
• Firoj Ahmed and
• Masami Ishibashi

Beilstein J. Org. Chem. 2014, 10, 134–140, doi:10.3762/bjoc.10.10

• previously described method [18]. Detection of the Hh inhibitory activity was based on the decrease in the luminescence value due to reduced luciferase expression by GLI1 compared to that of the control (DMSO). In addition we always checked the cytotoxicity of the compounds against the assay cells, because a

Synthesis, characterization and luminescence studies of gold(I)–NHC amide complexes

• Adrián Gómez-Suárez,
• David J. Nelson,
• David G. Thompson,
• David B. Cordes,
• Duncan Graham,
• Alexandra M. Z. Slawin and
• Steven P. Nolan

Beilstein J. Org. Chem. 2013, 9, 2216–2223, doi:10.3762/bjoc.9.260

• = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) with a series of commercially available (hetero)aromatic amines leads to the synthesis of several [Au(NRR’)(IPr)] complexes in good yields and with water as the sole byproduct. Interestingly, these complexes present luminescence properties. UV–vis and

• species as luminescent materials. We began our luminescence studies by recording the UV–vis spectra of the aforementioned gold–amide complexes using a dilute (ca. 0.2 mmol/L) CH2Cl2 solution. The wavelengths of the absorption maxima on the UV–vis spectra were in the range of 250–350 nm for most complexes

• . Lifetimes for all luminescence measurements were ≤1 μs (at the limit of the apparatus), suggesting that the luminescence was due to fluorescence, rather than phosphorescence. The wavelengths of emission maxima spans the range 390 to 516 nm, demonstrating that by selecting the appropriate amine ligand the