Synthesis of multi-lactose-appended β-cyclodextrin and its cholesterol-lowering effects in Niemann–Pick type C disease-like HepG2 cells

• Keiichi Motoyama,
• Rena Nishiyama,
• Yuki Maeda,
• Taishi Higashi,
• Yoichi Ishitsuka,
• Yuki Kondo,
• Tetsumi Irie,
• Takumi Era and
• Hidetoshi Arima

Beilstein J. Org. Chem. 2017, 13, 10–18, doi:10.3762/bjoc.13.2

• cyanotrihydroborate in dimethyl sulfoxide (DMSO) at 90 °C for 24 h. The product yield of multi-Lac-β-CD was 25%, and no unreacted compounds were confirmed by thin-layer chromatography (TLC). The MALDI–TOF MS spectrum of multi-Lac-β-CD revealed several peaks at m/z 2804, m/z 3006, m/z 3139, m/z 3296, and m/z 3454

• significant. Schematic representation for synthesis of multi-Lac-β-CD (5), β-CD (1), per-chloro-β-CD (2), per-azido-β-CD (3), per-amino-β-CD, (4), multi-Lac-β-CD (DSL5.6), DSL, degree of substitution of lactose, DMAc, dimethylacetamide. MALDI–TOFMS (A) and 1H NMR spectra (B) of multi-Lac-β-CD (DSL5.6

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

• , C(CH3)3), 141.15 (24C, C60 sp2), 145.99 (24C, C60 sp2), 163.75 (12C, O2CCH2CO2), 171.89 ppm (12C, CO2 t-Bu); UV–vis (CH2Cl2) λ: 281, 315 (sh), 334 (sh) nm; MS (MALDI, DCTB, pos) m/z: 3038 [M]+; anal, calcd for C174H180O48: C, 68.76; H, 5.97; found: C, 68.87; H, 6.09. Hexakisadduct C4: TFA (1.7 mL

• , rt) δ 23.47 (12C, CH2CO2H), 29.71 (12C, CH2CH2CH2), 45.44 (6C, O2CCH2CO2), 66.35 (12C, COOCH2), 68.67 (12C, C60 sp3), 140.71 (24C, C60 sp2), 145.02 (24C, C60 sp2), 162.75 (12C, O2CCH2CO2), 173.64 ppm (12C, CO2H); UV–vis (CH2Cl2) λ: 281, 315 (sh), 334 (sh) nm; MS (MALDI, DCTB, pos) m/z: 2365 [M

Biochemical and structural characterisation of the second oxidative crosslinking step during the biosynthesis of the glycopeptide antibiotic A47934

• Veronika Ulrich,
• Clara Brieke and
• Max J. Cryle

Beilstein J. Org. Chem. 2016, 12, 2849–2864, doi:10.3762/bjoc.12.284

• Scientific, Waltham, USA) and the calculated extinction coefficient of the protein at λ = 280 nm. Furthermore, the protein identity was confirmed by MALDI–TOF MS peptide map fingerprinting of a tryptic digest of excised protein bands from SDS-PAGE analysis. StaF was finally stored in SEC buffer in aliquots

A self-assembled cyclodextrin nanocarrier for photoreactive squaraine

• Ulrike Kauscher and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2016, 12, 2535–2542, doi:10.3762/bjoc.12.248

• , 17-C), 29.47, 29.38 (2CH2, 14-C), 28.38 (2CH, 22-C), 26.09, 26.02 (2CH2, 15-C), 25.99, 25.76 (2CH2, 16-C), 18.69 ppm; MALDI–MS (m/z): calcd for [C54H68N2O4S2]+: 872,46; found: 872,47. Schematic representation of adamantane-substituted squaraine (AdSq) binding as a divalent guest to the surface of

High performance p-type molecular electron donors for OPV applications via alkylthiophene catenation chromophore extension

• Paul B. Geraghty,
• Calvin Lee,
• Jegadesan Subbiah,
• Wallace W. H. Wong,
• James L. Banal,
• Mohammed A. Jameel,
• Trevor A. Smith and
• David J. Jones

Beilstein J. Org. Chem. 2016, 12, 2298–2314, doi:10.3762/bjoc.12.223

• solar cells. Supporting Information Supporting Information File 390: Synthetic procedures, NMR spectra, MALDI, TGA, DSC, CVs, POM methods and images, UV–vis, fluorescence, and DFT cartesian coordinates. Acknowledgements This work was made possible by support from the Australian Renewable Energy Agency

Determination of the absolute stereostructure of a cyclic azobenzene from the crystal structure of the precursor containing a heavy element

• Reji Thomas and
• Nobuyuki Tamaoki

Beilstein J. Org. Chem. 2016, 12, 2211–2215, doi:10.3762/bjoc.12.212

• ionization time-of-flight mass spectrometry (MALDI–TOFMS) was performed with an Applied Biosystems Voyager-DE pro instrument. Absorption spectra were recorded with an Agilent 8453 spectrophotometer and the CD spectra were recorded with a JASCO J-S720 CD spectrophotometer. High-performance liquid

Superelectrophilic activation of 5-hydroxymethylfurfural and 2,5-diformylfuran: organic synthesis based on biomass-derived products

• Dmitry S. Ryabukhin,
• Dmitry N. Zakusilo,
• Mikhail O. Kompanets,
• Anton A.Tarakanov,
• Irina A. Boyarskaya,
• Tatiana O. Artamonova,
• Mikhail A. Khohodorkovskiy,
• Iosyp O. Opeida and
• Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2016, 12, 2125–2135, doi:10.3762/bjoc.12.202

• superacid TfOH o- and m-xylenes gave rise to complex oligomeric mixtures (Table 5, entries 10 and 12) having masses up to 1400–1500 Da according to MALDI–MS (see Supporting Information File 1). These oligomers may have formed due to the participation of both aldehyde groups of species D (see Scheme 1 and

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

• mass spectrometry (MALDI–TOF). The proton and carbon NMR spectra unambiguously support the formation of the oligomers 3, and expectedly, in agreement with the molecular symmetry, the appearance of one (3a), two (3b), and three (3c) distinct resonances for the nitrogen-bound methylene carbon nuclei in

• ), 128.4 (2CH), 129.6 (2Cquat), 142.5 (2Cquat), 145.5 (2Cquat), 145.8 (2Cquat); MS (MALDI) m/z: 646.3 ([M]+); UV–vis (CH2Cl2), λmax [nm] (ε): 246 (39600), 261 (39100), 318 (27000), 395 (33100); IR (KBr) [cm−1]: 3057 (w), 2951 (w), 2926 (w), 2851 (w), 1917 (w), 1597 (w), 1576 (w), 1539 (w), 1489 (w), 1458

• (Cquat); MS (MALDI) m/z: 1208.5 ([M]+); UV–vis (CH2Cl2), λmax [nm] (ε): 266 (52100), 284 (45900), 319 (32500), 404 (27700); IR (KBr) [cm−1]: 2951 (w), 2922 (w), 2853 (w), 1456 (s), 1416 (w), 1375 (w), 1364 (w), 1331 (m), 1292 (w), 1238 (m), 1192 (w), 1138 (w), 1105 (w), 1063 (w), 1040 (w), 872 (m), 797

Synthesis and characterization of fluorinated azadipyrromethene complexes as acceptors for organic photovoltaics

• Forrest S. Etheridge,
• Roshan J. Fernando,
• Sandra Pejić,
• Matthias Zeller and
• Geneviève Sauvé

Beilstein J. Org. Chem. 2016, 12, 1925–1938, doi:10.3762/bjoc.12.182

• analogs for the synthesis of L3 and L4 were synthesized according to literature procedures and used without purification [35][36]. The Stille cross coupling reactions for the synthesis of L3 and L4 were monitored by MALDI–TOF–MS and were found to not be complete after increasing the reaction time to 48 h

• spectroscopy, MALDI–TOF–MS and elemental analysis. In the case of L2, the pure BF2+ chelate could not be isolated by column chromatography, and will therefore be omitted from further analysis. The thermal stability of the zinc(II) complexes was examined by thermal gravity analysis and the results are shown in

• spectra were recorded using a 500 MHz Bruker Ascend Avance III HDTM equipped with ProdigyTM ultra-high sensitivity Multinuclear Broadband CryoProbe or a Varian 400 MHz spectrometer in parts-per-million with respect to tetramethylsilane. MALDI–TOF–MS samples were prepared from chloroform solutions in a

Effect of the π-conjugation length on the properties and photovoltaic performance of A–π–D–π–A type oligothiophenes with a 4,8-bis(thienyl)benzo[1,2-b:4,5-b′]dithiophene core

• Ni Yin,
• Lilei Wang,
• Yi Lin,
• Jinduo Yi,
• Lingpeng Yan,
• Junyan Dou,
• Hai-Bo Yang,
• Xin Zhao and
• Chang-Qi Ma

Beilstein J. Org. Chem. 2016, 12, 1788–1797, doi:10.3762/bjoc.12.169

• solar cells based on COOP-nHT-TBDT at different blend ratios, a J–V comparison of devices based on 4:PC61BM and 4:PC71BM, UV–vis absorption spectra of COOP-nHT-TBDT:PC61BM blended films, as well as the NMR and MALDI–TOF MS spectra of COOP-nHT-TBDT. Supporting Information File 274: Additional

Organic chemistry meets polymers, nanoscience, therapeutics and diagnostics

• Vincent M. Rotello

Beilstein J. Org. Chem. 2016, 12, 1638–1646, doi:10.3762/bjoc.12.161

• notion of taking some cells, putting in nanoparticles, and then throwing them in the matrix-assisted laser desorption ionization (MALDI) mass spectrometer without matrix. Quite surprisingly, all the student could see was the ligand on the particle – with essentially no signal from all of the rest of the

Star-shaped and linear π-conjugated oligomers consisting of a tetrathienoanthracene core and multiple diketopyrrolopyrrole arms for organic solar cells

• Hideaki Komiyama,
• Chihaya Adachi and
• Takuma Yasuda

Beilstein J. Org. Chem. 2016, 12, 1459–1466, doi:10.3762/bjoc.12.142

• photoabsorption properties. Experimental General methods Matrix-assisted laser desorption ionization time-of-flight (MALDI–TOF) mass spectra were collected on a Bruker Daltonics Autoflex III spectrometer using dithranol as the matrix. Elemental analysis was carried out using a YANACO CHN coder MT-6

• provide TTA-DPP4 as a dark purple solid. This compound was further purified by recycling preparative gel permeation chromatography (GPC; eluent: chloroform) prior to use (yield = 0.36 g, 44%). MS (MALDI–TOF) m/z: [M]+ calcd for 3133.42; found 3133.51; anal. calcd (%) for C190H226N8O8S12: C, 72.80; H, 7.27

• mmol), and Pd(PPh3)4 (0.015 g, 0.013 mmol). The product was purified by silica gel column chromatography (eluent: chloroform/hexane 1:1, v/v) and GPC to give TTA-DPP2 as a dark purple solid (yield = 0.32 g, 49%). MS (MALDI–TOF) m/z: [M]+ calcd for 1991.95; found 1991.67; anal. calcd (%) for

Automated glycan assembly of a S. pneumoniae serotype 3 CPS antigen

• Markus W. Weishaupt,
• Stefan Matthies,
• Mattan Hurevich,
• Claney L. Pereira,
• Heung Sik Hahm and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2016, 12, 1440–1446, doi:10.3762/bjoc.12.139

• of the glycosylation solutions exiting the reaction chamber was tested and found to be strongly acidic. After cleavage from the solid support, HPLC analysis of the crude product showed one major product (Figure 4). However, MALDI–TOF MS analysis indicated that this fraction corresponded to a

• . Acknowledgements We thank the Max Planck Society and the BMBF (Das Taschentuchlabor: Impulszentrum für integrierte Bioanalyse (IZIB), Förderkennzeichen 03IS2201G) for financial support. We also thank Mrs. Eva Settels and Ms. Janine Stuwe for MALDI–TOF measurements. Furthermore, we would like to thank Dr. Sebastian

3,6-Carbazole vs 2,7-carbazole: A comparative study of hole-transporting polymeric materials for inorganic–organic hybrid perovskite solar cells

• Wei Li,
• Munechika Otsuka,
• Takehito Kato,
• Yang Wang,
• Takehiko Mori and
• Tsuyoshi Michinobu

Beilstein J. Org. Chem. 2016, 12, 1401–1409, doi:10.3762/bjoc.12.134

• , 28.74, 27.71, 27.32, 26.96, 26.73, 24.27, 22.96, 17.37, 13.94, 13.58, 13.48, 10.75, 9.59 ppm; FTIR (neat) ν: 2955, 2923, 2852, 2361, 1798, 1652, 1614, 1581, 1462, 1419, 1376, 1342, 1276, 1258, 1218, 1143, 1063, 1014, 961, 867, 794, 749, 698, 679, 654, 624, 607 cm−1; MALDI–TOF MS (Mw = 859.4): m/z

• , 14.00, 11.21, 10.08, 7.84 ppm; FTIR (neat) v: 2955, 2923, 2870, 2852, 1485, 1458, 1441, 1415, 1376, 1339, 1319, 1250, 1200, 1146, 1071, 996, 962, 911, 860, 826, 814, 794, 741, 723, 710, 695, 653, 633, 616 cm−1; MALDI–TOF MS (Mw = 859.4): m/z = 860.5 ([M + H]+). Synthesis of 3,6-Cbz-EDOT Analogously to

• on a JASCO FT/IR-4100 spectrometer in the range from 4000 to 600 cm−1. MALDI–TOF mass spectra were measured on a Shimadzu/Kratos AXIMA-CFR mass spectrometer equipped with nitrogen laser (λ = 337 nm) and pulsed ion extraction, which was operated in a linear-positive ion mode at an accelerating

Artificial Diels–Alderase based on the transmembrane protein FhuA

• Hassan Osseili,
• Daniel F. Sauer,
• Klaus Beckerle,
• Marcus Arlt,
• Tomoki Himiyama,
• Tino Polen,
• Akira Onoda,
• Ulrich Schwaneberg,
• Takashi Hayashi and
• Jun Okuda

Beilstein J. Org. Chem. 2016, 12, 1314–1321, doi:10.3762/bjoc.12.124

• oxidized to Cu(II) by contamination with air. Cu(II) led to protein aggregation and precipitation. This was shown in an independent experiment. When one equiv of Cu(NO3)2·3H2O was added to a solution of FhuA ΔCVFtev, the protein precipitated rapidly and quantitatively. MALDI–TOF–MS analysis for the whole

• catalyst 17 was successful. Comparison of the MALDI–TOF– MS spectrum with FhuA ΔCVFtev (calcd (M + Na+): m/z = 5925 Da; found: m/z = 5925 Da) indicates successful coupling. The signal of m/z = 6301 Da indicates the FhuA fragment with the attached ligand framework (calcd (M): m/z = 6302 Da; found: m/z

• = 6301 Da). The signal of m/z = 6111 Da results from saponification of the ester and the maleimide moiety (calcd (M + H2O + Na+): m/z = 6111 Da, found: m/z = 6111 Da). We were unable to detect the copper ion in the MALDI–TOF–MS. The isolated biohybrid catalysts were tested in the Diels–Alder reaction of

Aluminacyclopentanes in the synthesis of 3-substituted phospholanes and α,ω-bisphospholanes

• Vladimir A. D’yakonov,
• Alevtina L. Makhamatkhanova,
• Rina A. Agliullina,
• Leisan K. Dilmukhametova,
• Tat’yana V. Tyumkina and
• Usein M. Dzhemilev

Beilstein J. Org. Chem. 2016, 12, 406–412, doi:10.3762/bjoc.12.43

• , C(3)), 43.02 (JPC = 1.0 Hz, C(3)), 126.87 (C(9)), 127.90, 127.91 (JPC = 5.0 Hz, C(8), C(10)), 130.07 (JPC = 16.1 Hz, C(7), C(11)), 130.13 (JPC = 15.1 Hz, C(7), C(11)), 142.47, 142.84 (JPC = 23.1 Hz, C(6)) (P-Ph); 31P NMR (161.97 MHz, CDCl3) δ −13.5, −13.9; MALDI–TOF: m/z сalcd for C18H30P ([M + H

• ), C(10)), 129.55 (JPC = 10.1 Hz, C(7), C(11)), 131.40 (JPC = 3.0 Hz, C(9)), 133.90 (JPC = 89.5 Hz, C(6)), 134.00 (JPC = 90.5 Hz, C(6)) (P-Ph); 31P NMR (161.97 MHz, CDCl3) δ 59.7, 59.4; MALDI TOF: m/z calculated for C18H30OP ([M+ H]+): 293.4040; found: 293.5. General procedure for the preparation of 3

• )), 41.94 (JPC = 54.3 Hz, С(2)), 42.38 (JPC = 53.3 Hz, C(2)), 128.30 (JPC = 12.1 Hz, C(8), C(10)), 130.00 (JPC = 11.1 Hz, C(7), C(11)), 131.07 (JPC = 2.0 Hz, C(9)), 133.76, 133.84 (JPC = 70.4 Hz, C(6)) (P-Ph); 31P NMR (161.97 MHz, CDCl3) δ 57.72; MALDI TOF: m/z сalculated for C16H26PS ([M + H]+): 281.4174

Size-controlled and redox-responsive supramolecular nanoparticles

• Raquel Mejia-Ariza,
• Gavin A. Kronig and
• Jurriaan Huskens

Beilstein J. Org. Chem. 2015, 11, 2388–2399, doi:10.3762/bjoc.11.260

• chemical shift value, 400 MHz is reported as δ using the residual solvent signal as internal standard at ≈22 °C. Mass spectrometry Mass analysis was done using matrix-assisted laser desorption ionization (MALDI) on a Waters Synapt G1 using 2,5-dihydroxybenzoic acid as the matrix. Microcalorimetric

Convenient preparation of high molecular weight poly(dimethylsiloxane) using thermally latent NHC-catalysis: a structure-activity correlation

• Stefan Naumann,
• Johannes Klein,
• Dongren Wang and
• Michael R. Buchmeiser

Beilstein J. Org. Chem. 2015, 11, 2261–2266, doi:10.3762/bjoc.11.246

• up, ranging from 200 000 g/mol to over 400 000 g/mol (Mn). Importantly, in all these cases very high conversion is observed. Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI–ToF MS) and NMR experiments clearly show that BnOH is incorporated in the resulting PDMS (S1

Easy access to heterobimetallic complexes for medical imaging applications via microwave-enhanced cycloaddition

• Nicolas Desbois,
• Sandrine Pacquelet,
• Adrien Dubois,
• Clément Michelin and
• Claude P. Gros

Beilstein J. Org. Chem. 2015, 11, 2202–2208, doi:10.3762/bjoc.11.239

• dissolved in benzonitrile and then refluxed to yield 9d. The target metalated porphyrins 9a–d were isolated in moderate to good yields ranging from 51 to 82% and were fully characterized by 1H NMR, MS (MALDI–TOF) and HRMS (ESI) spectrometry. Alkynyl DOTA/NOTA In a second step, the successful preparation of

Cholesterol lowering effects of mono-lactose-appended β-cyclodextrin in Niemann–Pick type C disease-like HepG2 cells

• Keiichi Motoyama,
• Yumi Hirai,
• Rena Nishiyama,
• Yuki Maeda,
• Taishi Higashi,
• Yoichi Ishitsuka,
• Yuki Kondo,
• Tetsumi Irie,
• Takumi Era and
• Hidetoshi Arima

Beilstein J. Org. Chem. 2015, 11, 2079–2086, doi:10.3762/bjoc.11.224

• , lactose was modified to NH2-β-CyD using the reducing agent cyanotrihydroborate in dimethyl sulfoxide (DMSO) at room temperature for 24 h. No unreacted free lactose was confirmed by thin-layer chromatography (TLC). The MALDI–TOF MS spectrum of Lac-β-CyD showed a peak at m/z 1483 derived from lactose mono

• for protons at 25 °C. The concentration of the sample was 1.5 mg/750 μL in deuterated oxide (D2O), and the chemical shifts were given as parts per million (ppm) downfield from that of tetramethylsilane (TMS). MALDI-TOF mass spectra (MALDI–TOF MS) were measured in a positive mode at 25 °C by a JEOL JMS

• with Scheffe's test. The level of statistical significance was set at p < 0.05. Preparation scheme of Lac-β-CyD. MALDI–TOF MS (A) and 1H NMR (B) spectra of Lac-β-CyD. Cytotoxic activity of β-CyDs in U18666A-treated HepG2 cells after treatment for 24 h. U18666A-treated HepG2 cells were incubated with

Polythiophene and oligothiophene systems modified by TTF electroactive units for organic electronics

• Alexander L. Kanibolotsky,
• Neil J. Findlay and
• Peter J. Skabara

Beilstein J. Org. Chem. 2015, 11, 1749–1766, doi:10.3762/bjoc.11.191

• ) revealed by GPC analysis (Table 2) corresponds to about 7 thienoTTF monomer units per polymer chain for 35 and 37, and about 6 units for 39. MALDI–TOF MS characterisation was only successful for polymer 39 and showed a series of peaks with a mass difference of 516 Da, corresponding to the mass of the 2

• -(4,5-bis(hexylthio)-1,3-dithiol-2-ylidene)thieno[3,4-d][1,3]dithiol-4,6-diyl-alt-vinylene repeating unit. The mass spectra confirmed that the polymer was end-capped with a thienoTTF unit, with the terminal bromo substituents still intact. The highest mass peak of 5290 Da registered by MALDI–MS

Robust bifunctional aluminium–salen catalysts for the preparation of cyclic carbonates from carbon dioxide and epoxides

• Yuri A. Rulev,
• Zalina Gugkaeva,
• Victor I. Maleev,
• Michael North and
• Yuri N. Belokon

Beilstein J. Org. Chem. 2015, 11, 1614–1623, doi:10.3762/bjoc.11.176

• cyclic [32] or polycarbonate [33][34] from cyclohexene oxide, depending on the exact structure of the catalyst and cocatalyst. However, this is the first report of a one-component aluminium–salen-based catalyst for polycyclohexene carbonate synthesis. MALDI–TOF mass-spectra data (Figure 2) showed that

• (Figure 3) was consistent with the MALDI–TOF data, showing that most of the polymer has a molecular weight between 300 and 1000 Daltons. This type of low molecular weight polycarbonate–polyol is currently attracting much interest associated with its use in sustainable polyurethanes [35]. To show the

• Spectrometry Service Unit using ESI and MALDI ionization methods. GPC was carried out using a set (PSS SDV High) of 3 analytical columns (300 × 8 mm, particle diameter 5 µm) of 1000, 105 and 106 Å pore sizes, plus guard column, supplied by Polymer Standards Service GmbH (PSS) installed in a PSS SECcurity

Tetrathiafulvalene-based azine ligands for anion and metal cation coordination

• Awatef Ayadi,
• Aziz El Alamy,
• Olivier Alévêque,
• Magali Allain,
• Nabil Zouari,
• Mohammed Bouachrine and
• Abdelkrim El-Ghayoury

Beilstein J. Org. Chem. 2015, 11, 1379–1391, doi:10.3762/bjoc.11.149

• , 107.5 ppm; anal. calcd for C12H7NOS4: C, 46.58; H, 2.28; N, 4.53; found: C, 46.16; H, 2.22; N, 4.43; MALDI–TOF MS calcd: m/z = 309.5. found: m/z = 308.9 [M]+; HRMS (M): calcd for C12H7NOS4: 308.9410; found: 308.9413. 5-([2,2’-Bi(1,3-dithiolylidene)]-4-yl)picolinaldehyde (2): This compound was prepared

• , 131.8, 130.8, 122.6, 122.5, 120.7, 120.6, 114.2, 105.7 ppm; anal. calcd for C12H7NOS4: C, 46.58; H, 2.28; N, 4.53; found: C, 46.54; H, 2.20; N, 4.51; MALDI–TOF MS calcd: m/z = 309.5. found: m/z = 308.9 [M]+. HRMS (M): calcd for C12H7NOS4: 308.9410; found: 308.9404. 2-([2,2’-Bi(1,3-dithiolylidene)]-4-yl

• . calcd for C18H11N5O4S4: C, 44.15; H, 2.26; N, 14.30, found: C, 43.54; H, 2.22; N, 13.66; MALDI–TOF MS calcd: m/z = 489.6. found: m/z = 489.1 [M]+; HRMS (M): calcd for C18H11N5O4S4: 488.9694; found: 488.9687. 5-([2,2’-bi(1,3-dithiolylidene)]-4-yl)-2-((2,4-dinitrophenyl)hydrazono)methyl)pyridine (L2

Regioselective synthesis of chiral dimethyl-bis(ethylenedithio)tetrathiafulvalene sulfones

• Flavia Pop and
• Narcis Avarvari

Beilstein J. Org. Chem. 2015, 11, 1105–1111, doi:10.3762/bjoc.11.124

• TMS. The following abbreviations are used: d, doublet; t, triplet; m, multiplet. MALDI–TOF MS spectra were recorded on a Bruker Biflex-IIITM apparatus, equipped with a 337 nm N2 laser. Elemental analyses were recorded using Flash 2000 Fisher Scientific Thermo Electron analyzer. The starting compounds

• chromatography using petroleum spirit/dichloromethane 1:1 followed by dichloromethane as eluent, to afford an orange solid (0.53 g, 48%). 1H NMR (300 MHz, CDCl3) δ 3.23–3.17 (m, 2H, -CH-CH3), 3.06 (t, 2H, -CH2-), 2.71 (t, 2H, -CH2-), 1.42 (d, 6H, -CH3) ppm; MALDI–TOF MS (m/z): [M − CH2CH2CN)]+ 437.4; Anal. calcd

• , 116.56, 112.02, 111.44, 50.10, 44.04, 30.38, 27.39, 21.36 ppm; MALDI–TOF MS (m/z): 444 [M]+ (Mcalcd = 443.86); Anal. calcd for C12H12O2S8: C, 32.41; H, 2.72; O, 7.19; S, 57.68; found: C, 32.72; H, 2.55; O, 6.95; S, 57.93 (%). (R,R)-1: The same synthetic procedure was followed as for the (S,S)-enantiomer

Interactions between tetrathiafulvalene units in dimeric structures – the influence of cyclic cores

• Huixin Jiang,
• Virginia Mazzanti,
• Christian R. Parker,
• Søren Lindbæk Broman,
• Jens Heide Wallberg,
• Karol Lušpai,
• Adam Brincko,
• Henrik G. Kjaergaard,
• Anders Kadziola,
• Peter Rapta,
• Ole Hammerich and
• Mogens Brøndsted Nielsen

Beilstein J. Org. Chem. 2015, 11, 930–948, doi:10.3762/bjoc.11.104

• spectrometry (MS) was performed using Matrix Assisted Laser Desorption Ionization (MALDI); TOF = time-of-flight; FT-ICR = Fourier Transform Ion Cyclotron Resonance. IR spectra were measured using the attenuated total reflectance (ATR) method on diamond. The relative peak intensities in IR spectra are

• ); MS (MALDI–TOF): m/z = 476 [M•+]; HRMS (MALDI+, FT-ICR, dithranol): m/z = 476.02777 [M•+] (calcd for C19H28S6Si+: 476.02790). 1,2-Bis(4,5-bis(butylthio)tetrathiafulvalene)ethyne (4). To a solution of K2CO3 (121 mg, 0.88 mmol) in MeOH (30 mL) was added a solution of 10 (56 mg, 0.12 mmol) in THF (5 mL

• , 2H), 2.83–2.80 (m, 8H), 1.63–1.59 (m, 8H), 1.46–1.41 (m, 8H), 0.93 (t, J = 7.4 Hz, 6H), 0.92 (t, J = 7.4 Hz, 6H) ppm; 13C NMR (126 MHz, CDCl3) δ 128.28, 127.77, 126.50, 114.90, 111.75, 110.43, 84.61, 36.20, 36.19, 31.98, 31.91, 21.95, 13.75 ppm (2 signals missing); MS (MALDI–TOF): m/z = 782 [M