Trifluoromethyl-substituted tetrathiafulvalenes

• Olivier Jeannin,
• Frédéric Barrière and
• Marc Fourmigué

Beilstein J. Org. Chem. 2015, 11, 647–658, doi:10.3762/bjoc.11.73

• des Substances Naturelles (ISCN), Gif/Yvette (France). MALDI-TOF MS spectra were obtained from a Bruker Biflex-IIITM equipped with a 337 nm laser. Syntheses Preparation of EDT-TTF(CONH2)(CF3) (7): EDT-TTF(CO2Me)(CF3) (2bc) [17] (0.2 g, 0.47 mmol) was added to a MeOH solution (20 mL) saturated with

Functionalized branched EDOT-terthiophene copolymer films by electropolymerization and post-polymerization “click”-reactions

• Miriam Goll,
• Adrian Ruff,
• Erna Muks,
• Felix Goerigk,
• Beatrice Omiecienski,
• Ines Ruff,
• Rafael C. González-Cano,
• Juan T. Lopez Navarrete,
• M. Carmen Ruiz Delgado and
• Sabine Ludwigs

Beilstein J. Org. Chem. 2015, 11, 335–347, doi:10.3762/bjoc.11.39

• was set to 80 µm or 150 µm. Spectra are corrected for background. Modified electrodes were directly placed under the microscope. Data acquisition was performed with Thermo Fisher Scientific Omnic Picta software. Raman spectra with 532 laser excitation were recorded using a Bruker Senterra dispersive

• Raman microscope equipped with a neon lamp and using a Nd:YAG laser with excitation at λexc = 532 nm. Raman spectra with excitation at λexc = 488 nm were recorded by using a Microscope Invia ReflexRaman RENISHAW. Fourier Transform (FT) Raman spectra with 1064 nm laser excitation were recorded using a

• Bruker FRA 106/S instrument and a Nd:YAG laser source with excitation at λexc = 1064 nm, operating in a back-scattering configuration. Water contact angle measurements were carried out on a Contact Angle System OCA 20 by dataphysics using water droplets of 1–2 µL volume (R > 18.2 MΩ). Calculations of the

Formation of nanoparticles by cooperative inclusion between (S)-camptothecin-modified dextrans and β-cyclodextrin polymers

• Thorbjørn Terndrup Nielsen,
• Catherine Amiel,
• Laurent Duroux,
• Kim Lambertsen Larsen,
• Lars Wagner Städe,
• Reinhard Wimmer and
• Véronique Wintgens

Beilstein J. Org. Chem. 2015, 11, 147–154, doi:10.3762/bjoc.11.14

• scattering (DLS) using a Malvern Instruments Zetasizer Nano ZS equipped with a He–Ne laser (633 nm, scattering angle 173°). Each sample was measured ten times for ten seconds at 25 °C. Syntheses N3CPT CPT (500 mg, 1.434 mmol) and 6-azidohexanoic acid were dissolved in 75 mL DCM. DMAP (89 mg, 0.715 mmol) and

Modification of physical properties of poly(L-lactic acid) by addition of methyl-β-cyclodextrin

• Toshiyuki Suzuki,
• Ayaka Ei,
• Yoshihisa Takada,
• Hiroki Uehara,
• Takeshi Yamanobe and
• Keiko Takahashi

Beilstein J. Org. Chem. 2014, 10, 2997–3006, doi:10.3762/bjoc.10.318

• 10 °C min−1 under a nitrogen flow of 20 mL min−1. MeCD was used as received. DSC-Raman measurements A power compensation DSC (Perkin-Elmer DSC 8500) connected to a Raman spectrometer (Perkin-Elmer Raman Station 400) through a DSC-Raman interface probe was used. The laser irradiation of the samples

• and scattering collection from the samples were conducted through glass fibers to minimize the laser irradiation area and to avoid temperature changes. Laser irradiation was configured to 100 mW for 4 s with a heat flow amplitude of less than 8 mW or 0.03 °C [59]. The collection of Raman spectral data

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

• have found numerous applications as laser dyes [5][6][7], labels for biological imaging [8][9][10] and low band-gap polymers [11][12][13]. Being efficient emitters in solution, small molecule BODIPY compounds often show signs of aggregation at high concentration and in solid films [14][15], which

Linear-g-hyperbranched and cyclodextrin-based amphiphilic block copolymer as a multifunctional nanocarrier

• Yamei Zhao,
• Wei Tian,
• Guang Yang and
• Xiaodong Fan

Beilstein J. Org. Chem. 2014, 10, 2696–2703, doi:10.3762/bjoc.10.284

• laser light scattering (SEC/MALLS) results (Supporting Information File 1, Table S1 and Figure S4). Obviously, the ratio of chain length of PDMAEMA to PHEMA, 5:1, was high. The synthesis of P2 was then obtained via a pseudo-one-step hydrosilylation reaction (Supporting Information File 1, Scheme S2

Synthesis and characterization of a hyper-branched water-soluble β-cyclodextrin polymer

• Francesco Trotta,
• Fabrizio Caldera,
• Roberta Cavalli,
• Andrea Mele,
• Carlo Punta,
• Lucio Melone,
• Franca Castiglione,
• Barbara Rossi,
• Monica Ferro,
• Vincenza Crupi,
• Domenico Majolino,
• Valentina Venuti and
• Dominique Scalarone

Beilstein J. Org. Chem. 2014, 10, 2586–2593, doi:10.3762/bjoc.10.271

• collected in backscattering geometry in the wavenumber range of 100–3500 cm−1, by using an exciting radiation at 632.8 nm (He−Ne laser, power at the output ≈20 mW). The laser was focused onto the sample surface with a spot size of about 1 μm2 through the 80× objective (NA = 0.9) of a microprobe setup

A versatile δ-aminolevulinic acid (ΑLA)-cyclodextrin bimodal conjugate-prodrug for PDT applications with the help of intracellular chemistry

• Chrysie Aggelidou,
• Theodossis A. Theodossiou,
• Antonio Ricardo Gonçalves,
• Mariza Lampropoulou and
• Konstantina Yannakopoulou

Beilstein J. Org. Chem. 2014, 10, 2414–2420, doi:10.3762/bjoc.10.251

• and superimposition of the 1D images along the x-axis (Supporting Information File, Figure S7) revealed that the intensity of red fluorescence was measurably higher in both images taken from cells after treatment with 2 than in those treated with 1, irrespective of the laser intensity applied

• . Incubation with compound 1 and use of 100% laser intensity resulted in only small enhancement of red fluorescence. These qualitative results show that the conjugate 2 worked much more efficiently than 1 alone, either due to the multiplicity of 1 attached and/or due to more efficient cell penetration. What

• can be, however, deduced from the images in Figure 2 and Figure S7 is that although the 1-treated cells were imaged at more than 3-times the laser power used for the 2-treated cells, the latter exhibited a much more intense PpIX fluorescence. This indicates that it is not the 3×δ-aminolevulinic acid

Synthesis and immunological evaluation of protein conjugates of Neisseria meningitidis X capsular polysaccharide fragments

• Laura Morelli,
• Damiano Cancogni,
• Marta Tontini,
• Alberto Nilo,
• Sara Filippini,
• Paolo Costantino,
• Maria Rosaria Romano,
• Francesco Berti,
• Roberto Adamo and
• Luigi Lay

Beilstein J. Org. Chem. 2014, 10, 2367–2376, doi:10.3762/bjoc.10.247

• subsequently reconstituted with 10 mM NaPi pH 7. Yields (recovered glycoprotein as determined by microBCA, Pierce Thermo): 85–95%. Loading of glycoconjugate was determined by matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI–TOF MS; UltraFlex III MALDI–TOF/TOF instrument

Specific DNA duplex formation at an artificial lipid bilayer: fluorescence microscopy after Sybr Green I staining

• Emma Werz and
• Helmut Rosemeyer

Beilstein J. Org. Chem. 2014, 10, 2307–2321, doi:10.3762/bjoc.10.240

• it had been shown that a membrane-bound duplex formation between the lipo-oligonucleotide 7 (5’-d(1a-ATC CAG TTA TGA)-3’) and the oligomer 5 failed. Now, we repeated the first experiment (4 + 5) successfully and run a z-scan of the bilayer after 45 min of incubation with a laser irradiation of the

• Cy5 dye at 635 nm (Figure 2). Then, a Sybr Green I (3) solution in dimethyl sulfoxide (≈1 µg/mL) was added to the cis compartment of the slide. In the first experiment (A) laser irradiation of the intercalated dye was performed at 470 nm. In orienting experiments Sybr Green I was irradiated at 470 nm

• decreasing continuously and turned out to be stable. A confocal laser scanning microscope (Insight Cell 3D, Evotec Technologies GmbH, Hamburg, Germany) equipped with a 488 nm argon-ion laser, (Multiline, 2014-25MLYVW (max. total power 50 mW) from JDS Uniphase Corporation (Milpitas, CA,USA), as well as with a

Expanding the scope of cyclopropene reporters for the detection of metabolically engineered glycoproteins by Diels–Alder reactions

• Anne-Katrin Späte,
• Verena F. Schart,
• Julia Häfner,
• Andrea Niederwieser,
• Thomas U. Mayer and
• Valentin Wittmann

Beilstein J. Org. Chem. 2014, 10, 2235–2242, doi:10.3762/bjoc.10.232

• ], followed by labeling with streptavidin–AlexaFluor647 (streptavidin–AF647) (Scheme 3). With all three sugars staining of the plasma membrane was detected by confocal laser scanning microscopy of living cells (Figure 2A, B, C). Only the solvent control did not show any membrane staining (Figure 2D, for

• min–1; mobile phase: gradient of acetonitrile with 0.1% formic acid (solvent A) in water with 0.1% formic acid (solvent B). Microscopy was performed using a point laser scanning confocal microscope Zeiss LSM 510 Meta equipped with a Meta detector for spectral imaging. The synthesis of 1 and 2 was

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

• Edinburgh FLS 980 photoluminescence spectrometer with 1 cm quartz cells. A 375 nm pulsed diode laser (EPL-375, maximum average power: 5 mW, pulse width: 73.2 ps) was used as a light source. Decay data analysis was performed by the deconvolution procedure with multiexponential decay models. The quality of

Photo, thermal and chemical degradation of riboflavin

• Muhammad Ali Sheraz,
• Sadia Hafeez Kazi,
• Sofia Ahmed,
• Zubair Anwar and
• Iqbal Ahmad

Beilstein J. Org. Chem. 2014, 10, 1999–2012, doi:10.3762/bjoc.10.208

• it was found to be higher in D2O (66%) in comparison to that of distilled water (40%) [57]. The effects of various solvents on the rates of flavin redox reactions have been investigated using laser flash photolysis [50]. The effect of aqueous and organic solvents on the photolysis of FMF has been

Influence of cyclodextrin on the UCST- and LCST-behavior of poly(2-methacrylamido-caprolactam)-co-(N,N-dimethylacrylamide)

• Alexander Burkhart and
• Helmut Ritter

Beilstein J. Org. Chem. 2014, 10, 1951–1958, doi:10.3762/bjoc.10.203

• accomplished using a TP1 turbidity photometer in a temperature range of 5 to 70 °C. During continuous stirring, the transparency of the sample was determined by a voltage-controlled semiconductor or laser and a silicon photodiode at a wavelength of 590 nm and a heating or cooling rate of 1 °C min−1. The

Multivalent scaffolds induce galectin-3 aggregation into nanoparticles

• Candace K. Goodman,
• Mark L. Wolfenden,
• Pratima Nangia-Makker,
• Anna K. Michel,
• Avraham Raz and
• Mary J. Cloninger

Beilstein J. Org. Chem. 2014, 10, 1570–1577, doi:10.3762/bjoc.10.162

• functionalized dendrimers were characterized by MALDI–TOF–MS (matrix-assisted laser desorption time of flight mass spectrometry). The average numbers of sugars that were incorporated are shown in Scheme 2. The loadings were determined by both the changes in weight average molecular weight (Mw) upon addition of 1

• corresponding to 12–15 pmol of the analyte was deposited on the laser target. Positive ion mass spectra were acquired in linear mode and the ions were generated by using a nitrogen laser (337 nm) pulsed at 3 Hz with a pulse width of 3 nanoseconds. Ions were accelerated at 19,000–20,000 volts and amplified using

• nm laser and upgraded APD detector. Scattered light was detected at 90° incidence and optimized to a count rate of 200–400 kilocounts per second (kcps) through adjustment of a neutral density filter prior to the sample chamber. The intensity was maximized for samples producing less than 200 kcps

Bis(β-lactosyl)-[60]fullerene as novel class of glycolipids useful for the detection and the decontamination of biological toxins of the Ricinus communis family

• Hirofumi Dohi,
• Takeru Kanazawa,
• Akihiro Saito,
• Keita Sato,
• Hirotaka Uzawa,
• Yasuo Seto and
• Yoshihiro Nishida

Beilstein J. Org. Chem. 2014, 10, 1504–1512, doi:10.3762/bjoc.10.155

• a laser excitation imaging kit. The residual ricin concentration in the bis-Lac-C60 colloidal suspension was determined by means of the calibration curve, which shows the ricin intensities at each concentration. Estimation of decontamination efficiency by using a salting-out agent: A ricin solution

Multichromophoric sugar for fluorescence photoswitching

• Stéphane Maisonneuve,
• Rémi Métivier,
• Pei Yu,
• Keitaro Nakatani and
• Juan Xie

Beilstein J. Org. Chem. 2014, 10, 1471–1481, doi:10.3762/bjoc.10.151

• combination of 1H NMR and UV–visible absorption spectra, realized by successive irradiation at 335 nm for a total time of 20 min. Fluorescence intensity decays were obtained by the time-correlated single-photon counting (TCSPC) method with femtosecond laser excitation using a set-up composed of a Ti:Sa laser

• (Tsunami, Spectra-Physics) pumped by a doubled Nd:YAG cw-laser (Millennia, Spectra-Physics), pumped itself by two laser diode arrays. Light pulses at 950 nm were selected by optoacoustic crystals at a repetition rate of 4 MHz, and then doubled at 475 nm by non-linear crystals. Fluorescence photons were

Automated solid-phase peptide synthesis to obtain therapeutic peptides

• Veronika Mäde,
• Sylvia Els-Heindl and
• Annette G. Beck-Sickinger

Beilstein J. Org. Chem. 2014, 10, 1197–1212, doi:10.3762/bjoc.10.118

• major prerequisite for the success of SPPS, both with respect to analytics and preparative purification [25]. Furthermore, high-quality mass spectrometry (MS) with soft ionization techniques such as MALDI–TOF (matrix-assisted laser desorption ionization – time of flight) and ESI (electrospray ionization

Novel indolin-2-one-substituted methanofullerenes bearing long n-alkyl chains: synthesis and application in bulk-heterojunction solar cells

• Irina P. Romanova,
• Andrei V. Bogdanov,
• Inessa A. Izdelieva,
• Vasily A. Trukhanov,
• Gulnara R. Shaikhutdinova,
• Dmitry G. Yakhvarov,
• Shamil K. Latypov,
• Vladimir F. Mironov,
• Vladimir A. Dyakov,
• Ilya V. Golovnin,
• Dmitry Yu. Paraschuk and
• Oleg G. Sinyashin

Beilstein J. Org. Chem. 2014, 10, 1121–1128, doi:10.3762/bjoc.10.111

• Research Center of the Russian Academy of Sciences, Kazan 420088, Russian Federation Faculty of Physics and International Laser Center, M.V. Lomonosov Moscow State University, Moscow 119991, Russian Federation Faculty of Bioengineering and Bioinformatics, M.V. Lomonosov Moscow State University, Moscow

Tailoring of organic dyes with oxidoreductive compounds to obtain photocyclic radical generator systems exhibiting photocatalytic behavior

• Christian Ley,
• Julien Christmann,
• Ahmad Ibrahim,
• Luciano H. Di Stefano and
• Xavier Allonas

Beilstein J. Org. Chem. 2014, 10, 936–947, doi:10.3762/bjoc.10.92

• of this research area, the development of photoradical generators (PRG) is still a lively topic that finds applications in triggering bioactivity [1], drug or fragrance release [2][3][4], microelectronics [5], water catalysis reduction [6][7][8], and laser imaging [9]. In organic chemistry, the

• reaction. Thus, according to Beer–Lambert's law, the absorbance of the system decreases during the reaction: this bleaching could be followed by UV–visible absorption spectroscopy. The photolysis of an acetonitrile solution of RB/TA was done within a 1 cm width cell with a monochromatic 532 nm laser diode

• transmitted laser diode light was real-time recorded. It is thus possible to calculate the optical density A(t) of the sample, which is then converted into [RB](t). It can be seen from Figure 1 that a fast decrease of [RB](t) occurs, so fast that the very beginning is not resolved by the detector. This

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

• , among others, the following novel properties [45][46][47][48][49][50][51][52][53][54][55]: Almost no photoinitiator is consumed. Since the spectral photosensitivity extends now from the UV to the visible, laser excitation in the purple, blue, yellow, green or red is feasible. Low light intensities (as

• light sources (Hg, Xe or Hg–Xe lamps, laser diodes) can be obviously employed. However, and with more interest, very soft irradiation conditions (using, e.g., household fluorescence or LED bulbs, halogen lamps or even sunlight) are also suitable to polymerize radical and cationic monomers (see Figure 4

Thermodynamically stable [4 + 2] cycloadducts of lanthanum-encapsulated endohedral metallofullerenes

• Yuta Takano,
• Yuki Nagashima,
• M. Ángeles Herranz,
• Nazario Martín and
• Takeshi Akasaka

Beilstein J. Org. Chem. 2014, 10, 714–721, doi:10.3762/bjoc.10.65

• the cycloadducts (3a,b and 4a,b). The reactions were traced using HPLC analyses (Figure 1), and formation of the resulting [4 + 2] adducts was confirmed by matrix-assisted laser desorption ionization (MALDI) TOF mass spectrometry (Figure 2), which shows the molecular ion peaks for the corresponding

Synthesis and determination of the absolute configuration of (−)-(5R,6Z)-dendrolasin-5-acetate from the nudibranch Hypselodoris jacksoni

• I. Wayan Mudianta,
• Victoria L. Challinor,
• Anne E. Winters,
• Karen L. Cheney,
• James J. De Voss and
• Mary J. Garson

Beilstein J. Org. Chem. 2013, 9, 2925–2933, doi:10.3762/bjoc.9.329

• in n-hexane, flow rate of 0.5 mL min−1) equipped with UV (214 nm) and ALP (Advanced Laser Polarimeter, PDR-Chiral Inc.) detectors and a Chiralpak AD column (250 × 4.6 mm, Daicel Chemical Industries Ltd.). The preparative enantioselective HPLC purification of 7b used isocratic conditions (1.5

• -hexane, flow rate of 0.5 mL min−1) equipped with UV (220 nm) and ALP (Advanced Laser Polarimeter, PDR-Chiral Inc.) detectors and a Chiralpak OJ column (4.6 × 250 mm, Daicel Chemical Industries Ltd.). Retention times were: (+)-enantiomer, >97% ee 8.3 min; (–)-enantiomer, >98.5% ee 9.4 min; natural sample

Oligomeric epoxide–amine adducts based on 2-amino-N-isopropylacetamide and α-amino-ε-caprolactam: Solubility in presence of cyclodextrin and curing properties

• Julian Fischer and
• Helmut Ritter

Beilstein J. Org. Chem. 2013, 9, 2803–2811, doi:10.3762/bjoc.9.315

• peak as an internal standard. Fourier transform infrared (FTIR) spectra were recorded on a Nicolet 6700 FTIR spectrometer equipped with an ATR unit. Turbidity measurements were conducted using a Tepper TP1 cloud-point photometer equipped with a laser with a wavelength of 670 nm. For all experiments a

• spectrometry (ESIMS) was conducted on a Bruker maXis 4G mass spectrometer and matrix-assisted laser desorption-ionization time-of-flight mass spectrometry (MALDI-TOF-MS) on a Bruker Dalomics Ultraflex 1 mass spectrometer. Melting points were obtained using a Büchi Melting Point B-545 apparatus at a heating

• rate of 1 °C/min. Dynamic light scattering (DLS) experiments were conducted on a Malvern Zetasizer Nano ZS ZEN 3600 at a temperature of 20 °C with a laser wavelength of 633 nm and a detection angle of 173°. The non-negative-least-squares algorithm was used for interpretation. The samples were dissolved

Raman spectroscopy as a tool for monitoring mesoscale continuous-flow organic synthesis: Equipment interface and assessment in four medicinally-relevant reactions

• Trevor A. Hamlin and
• Nicholas E. Leadbeater

Beilstein J. Org. Chem. 2013, 9, 1843–1852, doi:10.3762/bjoc.9.215

• Raman probe near the reaction vessel, without requirement to place any parts of the spectrometer inside the reaction vessel. The exposure of metallic components to the microwave field was avoided using a quartz light-pipe extending both the excitation laser and the acquisition fiber optic components of