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

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