Development of fluorinated benzils and bisbenzils as room-temperature phosphorescent molecules

Shigeyuki Yamada,
Takuya Higashida,
Yizhou Wang,
Masato Morita,
Takuya Hosokai,
Kaveendra Maduwantha,
Kaveenga Rasika Koswattage and
Tsutomu Konno

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Published 29 May 2020

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1. Graphical Abstract
2. Figure 1: (A) Transition-metal-containing and (B) pure organic phosphorescent materials reported thus far (bp...
  
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3. Figure 2: (A) Chemical structures of fluorescent bistolane derivatives previously developed by our group and ...
  
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4. Scheme 1: Synthetic pathway for fluorinated benzil (2) and bisbenzil (3) derivatives.
  
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5. Scheme 2: Proposed mechanism of Pd(II)-catalyzed alkyne oxidation by dimethyl sulfoxide (DMSO).
  
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6. Figure 3: Mulliken charge distributions of fluorinated 1a and nonfluorinated 1c obtained from density functio...
  
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7. Figure 4: Absorption and photoluminescence (PL) spectra of (A) 2a, (B) 2b, (C) 3a, (D) 3b, and (E) 3c in tolu...
  
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8. Figure 5: Distributions of molecular orbitals (isosurface value: 0.04 a.u.) involved in vertical electronic t...
  
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Beilstein J. Org. Chem. 2020, 16, 1154–1162, doi:10.3762/bjoc.16.102

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Synthesis and properties of quinazoline-based versatile exciplex-forming compounds

Rasa Keruckiene,
Simona Vekteryte,
Ervinas Urbonas,
Matas Guzauskas,
Eigirdas Skuodis,
Dmytro Volyniuk and
Juozas V. Grazulevicius

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Published 28 May 2020

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1. Graphical Abstract
2. Scheme 1: Synthesis of quinazoline derivatives 1–3. Conditions: i) ammonium acetate, copper(II) chloride, iso...
  
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3. Figure 1: DSC (a, b, c) and TGA (d) curves of compounds 1–3. Scan rates were 20 °C/min (TGA) and 10 °C/min (D...
  
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4. Figure 2: Frontier-orbital distributions and optimized geometries at the ground state of quinazoline-based co...
  
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5. Figure 3: Cyclic voltammograms of quinazoline-based compounds 1–3.
  
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6. Figure 4: UV–vis absorption spectra of compounds 1–3. a) Theoretical and b) experimental spectra of compounds ...
  
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7. Figure 5: Fluorescence spectra (a) of dilute solutions and thin films of compounds 1–3 (λ_exc = 350 nm and PL ...
  
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8. Figure 6: Electron and hole NTOs of compounds 1–3 in the S1 excited state (vacuum).
  
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9. Figure 7: Chemical structures of exciplex-forming materials used, and visualization of white electroluminesce...
  
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Beilstein J. Org. Chem. 2020, 16, 1142–1153, doi:10.3762/bjoc.16.101

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A smart deoxyribozyme-based fluorescent sensor for in vitro detection of androgen receptor mRNA

Ekaterina A. Bryushkova,
Erik R. Gandalipov and
Julia V. Nuzhina

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Published 27 May 2020

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1. Graphical Abstract
2. Figure 1: SDFS main components and its work model. A) Schematic representation of the SDFS structure. Dotted ...
  
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3. Figure 2: The SDFS functional activity. A–C) Emission spectra of the assembled SDFS (green line), T1–T5 chain...
  
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4. Figure 3: Emission spectra of SDFS activity on total cellular RNA. The green line represents a spectrum of SD...
  
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Beilstein J. Org. Chem. 2020, 16, 1135–1141, doi:10.3762/bjoc.16.100

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The charge-assisted hydrogen-bonded organic framework (CAHOF) self-assembled from the conjugated acid of tetrakis(4-aminophenyl)methane and 2,6-naphthalenedisulfonate as a new class of recyclable Brønsted acid catalysts

Svetlana A. Kuznetsova,
Alexander S. Gak,
Yulia V. Nelyubina,
Vladimir A. Larionov,
Han Li,
Michael North,
Vladimir P. Zhereb,
Alexander F. Smol'yakov,
Artem O. Dmitrienko,
Michael G. Medvedev,
Igor S. Gerasimov,
Ashot S. Saghyan and
Yuri N. Belokon

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Published 26 May 2020

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1. Graphical Abstract
2. Scheme 1: The synthesis of F-1.
  
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3. Figure 1: View of the crystal structure of F-1 (F-1a phase), with representation of atoms by thermal ellipsoi...
  
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4. Figure 2: View of the crystal structure of F-1 (F-1a’ phase), with representation of the atoms via thermal el...
  
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5. Figure 3: SEM image of F-1.
  
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6. Figure 4: SEM image of F-1 with an F-1a phase.
  
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7. Figure 5: TGA-DSC analysis of a sample of F-1. The TGA plot is shown in green, the DSC curve is shown in blue...
  
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8. Scheme 2: Uncrystallized F-1 or F-1 with an F-1a phase promoted the two- and three-phase reactions of styrene...
  
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9. Scheme 3: CAHOF F-1-promoted reactions of cyclohexene oxide (5) with alcohols and water.
  
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10. Scheme 4: F-1-promoted Diels–Alder reaction.
  
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Beilstein J. Org. Chem. 2020, 16, 1124–1134, doi:10.3762/bjoc.16.99

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Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore

Esteban P. Urriolabeitia,
Pablo Sánchez,
Alexandra Pop,
Cristian Silvestru,
Eduardo Laga,
Ana I. Jiménez and
Carlos Cativiela

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Published 25 May 2020

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1. Graphical Abstract
2. Figure 1: (a) General scheme for truxillic acid derivatives; (b) general scheme for symmetric 1,3-diaminotrux...
  
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3. Figure 2: (a) (Z)-4-Arylidene-2-aryl-5(4H)-oxazolones used for the synthesis of 1,3-diaminotruxillic derivati...
  
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4. Figure 3: (Z)-4-Arylidene-2((E)-styryl)-5(4H)-oxazolones 2a–j used in this work and overall reaction scheme.
  
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5. Figure 4: Molecular drawing of the oxazolone 2c.
  
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6. Scheme 1: Ortho-palladation of oxazolones 2 by treatment with Pd(OAc)₂ and different structures obtained for ...
  
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7. Scheme 2: [2 + 2] Photocycloaddition of cyclopalladated complexes 3 in solution to give the dinuclear cyclobu...
  
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8. Figure 5: Molecular drawing of cyclobutane ortho-palladated 4a. Ellipsoids are shown at the 50% probability l...
  
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9. Scheme 3: Release of the 1,3-diaminotruxillic bis-amino ester derivatives 5 by methoxycarbonylation of the Pd...
  
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Beilstein J. Org. Chem. 2020, 16, 1111–1123, doi:10.3762/bjoc.16.98

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A cyclopeptide and three oligomycin-class polyketides produced by an underexplored actinomycete of the genus Pseudosporangium

Shun Saito,
Kota Atsumi,
Tao Zhou,
Keisuke Fukaya,
Daisuke Urabe,
Naoya Oku,
Md. Rokon Ul Karim,
Hisayuki Komaki and
Yasuhiro Igarashi

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Published 25 May 2020

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2. Figure 1: Structures of pseudosporamide (1) and pseudosporamicins A–C (2–4).
  
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3. Figure 2: COSY, key HMBC and ROESY correlations of pseudosporamide (1).
  
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4. Figure 3: ¹H NMR Δδ_S−R values for PGME amides 5a and 5b obtained from compound 1.
  
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5. Figure 4: The opposite axial chirality around the biaryl C-6–C-7'' bond influenced by the C-2 configuration i...
  
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6. Figure 5: The experimental and calculated ECD spectra in MeCN.
  
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7. Figure 6: COSY, key HMBC and NOESY correlations of compound 2.
  
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8. Figure 7: NOESY correlations for the spiroacetal moiety of compound 2.
  
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9. Figure 8: Selected examples of oligomycin-class metabolites from actinomycetes.
  
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Beilstein J. Org. Chem. 2020, 16, 1100–1110, doi:10.3762/bjoc.16.97

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A simple and easy to perform synthetic route to functionalized thienyl bicyclo[3.2.1]octadienes

Dragana Vuk,
Irena Škorić,
Valentina Milašinović,
Krešimir Molčanov and
Željko Marinić

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Published 22 May 2020

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1. Graphical Abstract
2. Figure 1: Known biologically active bicyclo[3.2.1]octenes/octadienes.
  
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3. Figure 2: Previously prepared bicyclo[3.2.1]octenes/octadienes with cholinesterase inhibitory properties.
  
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4. Scheme 1: Synthesis of annulated furobenzobicyclo[3.2.1]octadiene compounds.
  
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5. Scheme 2: Synthesis of annulated thiophenebicyclo[3.2.1]octadiene compounds 8-10.
  
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6. Scheme 3: Synthesis of compound 11.
  
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7. Figure 3: ¹H NMR spectra (CDCl₃) for the trans-isomers 3–6.
  
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8. Figure 4: UV spectra in ethanol (95%) of the cis- and trans-isomers of compound 3.
  
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9. Figure 5: Photolysis spectra of cis-3 (a) and trans-3 (b) in ethanol (95%).
  
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10. Figure 6: UV spectra in ethanol (95%) of the trans-isomers of compounds 3–7.
  
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11. Figure 7: Molecular structure of compound trans-6. Displacement ellipsoids are drawn for the probability of 3...
  
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12. Figure 8: Crystal packing of trans-6. (a) Chain parallel to [100] and (b) chain parallel to [010].
  
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13. Figure 9: ¹H NMR spectra (CDCl₃) of compounds 1, 8, and 9.
  
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14. Scheme 4: Synthesis of compound 12.
  
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15. Figure 10: UV spectra of compounds 1 and 12 in ethanol (95%).
  
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16. Figure 11: Photolysis spectra of compound 12 in ethanol (95%).
  
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17. Scheme 5: Possible outcomes of future photocatalytic oxygenation reactions of new benzobicyclo[3.2.1.]octadie...
  
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Beilstein J. Org. Chem. 2020, 16, 1092–1099, doi:10.3762/bjoc.16.96

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Palladium-catalyzed regio- and stereoselective synthesis of aryl and 3-indolyl-substituted 4-methylene-3,4-dihydroisoquinolin-1(2H)-ones

Valeria Nori,
Antonio Arcadi,
Armando Carlone,
Fabio Marinelli and
Marco Chiarini

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Published 20 May 2020

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1. Graphical Abstract
2. Scheme 1: Planned approach to tetrasubstituted-4-methylene-3,4-dihydroisoquinolin-1(2H)-ones 4 and 6.
  
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3. Scheme 2: Preparation of the starting N-propargyl-2-iodobenzamides 2.
  
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4. Scheme 3: Substrate scope of the reaction of N-propargyl-2-iodobenzamide 2a with arylboronic acids 3b–i.
  
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5. Scheme 4: Substrate scope of the reaction of N-propargyl-2-iodobenzamides 2c–f with arylboronic acids 3a–c/j.
  
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6. Scheme 5: Reaction of N-propargyl-2-iodobenzamides 2b,f with the 2-alkynyltrifluoroacetanilides 5a–c.
  
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Beilstein J. Org. Chem. 2020, 16, 1084–1091, doi:10.3762/bjoc.16.95

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Synthesis and anticancer activity of bis(2-arylimidazo[1,2-a]pyridin-3-yl) selenides and diselenides: the copper-catalyzed tandem C–H selenation of 2-arylimidazo[1,2-a]pyridine with selenium

Mio Matsumura,
Tsutomu Takahashi,
Hikari Yamauchi,
Shunsuke Sakuma,
Yukako Hayashi,
Tadashi Hyodo,
Tohru Obata,
Kentaro Yamaguchi,
Yasuyuki Fujiwara and
Shuji Yasuike

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Published 20 May 2020

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1. Graphical Abstract
2. Figure 1: Biologically active selenides and diselenides having heteroaryl groups.
  
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3. Figure 2: Ortep drawings of 2a (a and b) and 3a (c and d, thermal elipsoids indicate 50% probability).
  
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4. Figure 3: The synthesis of bis(2-arylimidazopyridin-3-yl) diselenides. Reaction conditions: 1 (2 mmol), Se (2...
  
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5. Figure 4: The synthesis of bis(2-arylimidazopyridin-3-yl) selenides. Reaction conditions: 1 (2 mmol), Se (1 m...
  
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6. Scheme 1: Control reactions.
  
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7. Scheme 2: Proposed mechanism (1).
  
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8. Scheme 3: Proposed mechanism (2).
  
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9. Figure 5: The cytotoxic effect of the bis(2-arylimidazo[1,2-a]pyridin-3-yl) diselenides 2 and selenides 3 on ...
  
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10. Figure 6: The cytotoxic effect of the bis[2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-yl] diselenide 2f on can...
  
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11. Figure 7: Cytotoxic effect of the bis[2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-yl] diselenide 2f on a cance...
  
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Beilstein J. Org. Chem. 2020, 16, 1075–1083, doi:10.3762/bjoc.16.94

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Synthesis of novel multifunctional carbazole-based molecules and their thermal, electrochemical and optical properties

Nuray Altinolcek,
Ahmet Battal,
Mustafa Tavasli,
William J. Peveler,
Holly A. Yu and
Peter J. Skabara

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Published 19 May 2020

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1. Graphical Abstract
2. Scheme 1: Synthesis of compounds 7a and 7b from carbazole 1. i) NBS, DMF, 0 °C to rt, 24 h. ii) n-hexyl bromi...
  
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3. Figure 1: TGA (a) and DSC (b) curve of the compounds 7a and 7b.
  
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4. Figure 2: Cyclic voltammograms of compounds 7a and 7b in dichloromethane under argon atmosphere at room tempe...
  
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5. Figure 3: Energy levels of compounds 7a and 7b.
  
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6. Figure 4: Normalised UV–vis and PL spectra of compounds 7a and 7b in dichloromethane.
  
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7. Figure 5: Normalised UV–vis spectra of compounds 7a and 7b in different solvents.
  
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8. Figure 6: PL spectra of compounds 7a and 7b in different solvents (A–H).
  
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Beilstein J. Org. Chem. 2020, 16, 1066–1074, doi:10.3762/bjoc.16.93

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