Complexation of a guanidinium-modified calixarene with diverse dyes and investigation of the corresponding photophysical response

Yu-Ying Wang,
Yong Kong,
Zhe Zheng,
Wen-Chao Geng,
Zi-Yi Zhao,
Hongwei Sun and
Dong-Sheng Guo

Full Research Paper
Published 25 Jun 2019

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1. Graphical Abstract
2. Scheme 1: (a) Schematic illustration of IDA. The addition of an analyte competitor leads to switch-on or swit...
  
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3. Scheme 2: (a) The chemical structure of GC5A and schematic illustration of the binding between the luminescen...
  
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4. Figure 1: Direct fluorescence titrations (λ_ex = 350 nm) of 2,6-TNS (1.0 μM) (a) and 1,8-ANS (1.0 μM) (c) with...
  
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5. Figure 2: (a) Direct fluorescence titration (λ_ex = 327 nm) of P-TPE (1.0 μM) with GC5A in HEPES buffer (10 mM...
  
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6. Figure 3: (a) Direct fluorescence titration (λ_ex = 371 nm) of TPS (1.0 μM) with GC5A in HEPES buffer (10 mM, ...
  
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7. Figure 4: (a) Direct fluorescence titration (λ_ex = 465 nm) of Ru(dcbpy)₃ (1.0 μM) with GC5A. (b) Direct absor...
  
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Beilstein J. Org. Chem. 2019, 15, 1394–1406, doi:10.3762/bjoc.15.139

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Selenophene-containing heterotriacenes by a C–Se coupling/cyclization reaction

Pierre-Olivier Schwartz,
Sebastian Förtsch,
Astrid Vogt,
Elena Mena-Osteritz and
Peter Bäuerle

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Published 24 Jun 2019

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1. Graphical Abstract
2. Figure 1: Heterotriacenes DTT 1, DTS 2, DST 3, and DSS 4 with varying number of selenium atoms and fused sele...
  
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3. Scheme 1: Synthesis of heterotriacenes DTT 1 and DTS 2 via copper-catalyzed cross-coupling reactions.
  
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4. Scheme 2: Synthesis of selenolotriacenes DST 3 and DSS 4.
  
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5. Figure 2: Single crystal X-ray structure analysis of selenolotriacene DST 3, (a) individual molecule and atom...
  
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6. Figure 3: Single crystal X-ray structure analysis of selenolotriacene DST 3: (a) partial overlap of stacked a...
  
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7. Figure 4: DFT quantum chemical calculated geometry of DTT 1 and general atom labelling for all heterotriacene...
  
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8. Figure 5: Representative electron density of frontier orbitals LUMO, HOMO, and HOMO-1 for heterotriacene DSS 4...
  
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9. Figure 6: Normalized absorption spectra of heteroacenes DTT 1 (black line), DTS 2 (blue line), DST 3 (green l...
  
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10. Figure 7: Energy diagram of the frontier molecular orbitals of heterotriacenes 1–4.
  
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11. Figure 8: Multisweep voltammograms for the electrochemical polymerization of monomeric heterotriacene DST 2 i...
  
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12. Scheme 3: Oxidative polymerization of heterotriacenes 1–4 to corresponding conjugated polymers P1–P4.
  
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Beilstein J. Org. Chem. 2019, 15, 1379–1393, doi:10.3762/bjoc.15.138

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Selective detection of DABCO using a supramolecular interconversion as fluorescence reporter

Indrajit Paul,
Debabrata Samanta,
Sudhakar Gaikwad and
Michael Schmittel

Letter
Published 21 Jun 2019

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1. Graphical Abstract
2. Figure 1: Molecular structures of ligands 1, 2, 3, and 4 and of the resulting products, i.e., rectangle 5, sa...
  
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3. Scheme 1: Guest addition/removal and reversible interconversion between supramolecular architectures.
  
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4. Scheme 2: Completive and incomplete self-sorting in presence of copper(I) and rhodium complex 3.
  
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5. Figure 2: Comparison of partial ¹H NMR spectra (400 MHz, CD₂Cl₂, 298 K) of (a) ligand 2; (b) ligand 1; (c) po...
  
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6. Figure 3: (a) UV–vis titration of rectangle 5 (2.98 μM) with DABCO (4); (b) several reversible cycles of inte...
  
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7. Scheme 3: The high selectivity for DABCO in the transformation.
  
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8. Figure 4: Partial spectra (400 MHz, CD₂Cl₂, 298 K) showing the reversible switching between rectangle and san...
  
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Beilstein J. Org. Chem. 2019, 15, 1371–1378, doi:10.3762/bjoc.15.137

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One-pot activation–alkynylation–cyclization synthesis of 1,5-diacyl-5-hydroxypyrazolines in a consecutive three-component fashion

Christina Görgen,
Katharina Boden,
Guido J. Reiss,
Walter Frank and
Thomas J. J. Müller

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Published 19 Jun 2019

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1. Graphical Abstract
2. Figure 1: Selected anticancer active 3,5-diaryl-1-acylpyrazoline (left) and xanthine oxygenase inhibitors (ce...
  
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3. Figure 2: Selected 1-acyl-5-hydroxypyrazolines with analgesic (left, center) and antibacterial activity (cent...
  
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4. Scheme 1: Glyoxylation–alkynylation (GA) and activation–alkynylation (AA) synthesis of alkynediones in a one-...
  
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5. Scheme 2: Consecutive three-component synthesis to give 5-benzoyl-3-phenyl-1H-pyrazole (6a) after alkaline de...
  
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6. Figure 3: ORTEP plot of 5-benzoyl-3-phenyl-1H-pyrazole (6a) (thermal ellipsoids at 30% probability); the dire...
  
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7. Scheme 3: Cyclization of 1,4-diphenylbut-3-yne-1,2-dione (3a) and Boc-hydrazine (4a) to give intermediate 5a.
  
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8. Figure 4: Ellipsoid plot of 1-Boc-5-benzoyl-5-hydroxypyrazoline 5a.
  
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9. Scheme 4: Model reaction for optimizing the activation–alkynylation–cyclization synthesis of 1,5-diacyl-5-hyd...
  
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10. Scheme 5: One-pot activation–alkynylation–cyclization synthesis of 1,5-diacyl-5-hydroxypyrazolines 5.
  
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11. Figure 5: ORTEP plot and dimer of compound 5r (thermal ellipsoids at 30% probability).
  
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Beilstein J. Org. Chem. 2019, 15, 1360–1370, doi:10.3762/bjoc.15.136

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Anomeric sugar boronic acid analogues as potential agents for boron neutron capture therapy

Daniela Imperio,
Erika Del Grosso,
Silvia Fallarini,
Grazia Lombardi and
Luigi Panza

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Published 19 Jun 2019

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1. Graphical Abstract
2. Figure 1: Structure of boronic acid analogues (for clarity, sugar numbering has been conserved into the analo...
  
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3. Figure 2: Structures of boron analogues.
  
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4. Figure 3: Synthetic strategy.
  
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5. Scheme 1: Synthesis of 2-deoxy analogue 8.
  
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6. Figure 4: Postulated transition states for the hydroboration reaction.
  
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7. Scheme 2: Synthesis of 2,3-dideoxy analogue 11.
  
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Beilstein J. Org. Chem. 2019, 15, 1355–1359, doi:10.3762/bjoc.15.135

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Formation of an unexpected 3,3-diphenyl-3H-indazole through a facile intramolecular [2 + 3] cycloaddition of the diazo intermediate

Andrew T. King,
Hugh G. Hiscocks,
Lidia Matesic,
Mohan Bhadbhade,
Roger Bishop and
Alison T. Ung

Full Research Paper
Published 19 Jun 2019

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1. Graphical Abstract
2. Figure 1: Examples of ¹⁸F-radiolabelled arylsulfonyl fluorides containing electron-donating 1, electron-withd...
  
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3. Scheme 1: Reaction for the formation of sulfonyl chloride 6 using DABSO.
  
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4. Figure 2: Possible compounds with the molecular formula C₃₃H₂₆N₂O (structure 7 contains 27 hydrogen atoms).
  
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5. Figure 3: ORTEP view of the molecule 8 showing the atom labelling (ellipsoids are drawn at 50% probability le...
  
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6. Figure 4: Significant intermolecular interactions made by the benzhydryl group (a, upper) and the gem-dipheny...
  
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7. Figure 5: Relationship of the C–H···N and cyclic C–H···H-C contacts in the crystal structure of 8. The centro...
  
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8. Figure 6: Part of a hydrocarbon tape along a formed by a combination of alternating linear and cyclic C–H···H...
  
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9. Scheme 2: Proposed mechanism for the formation of 8.
  
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10. Scheme 3: Direct preparation of compound 8. method a: t-BuONO, CuCl₂, dry CH₃CN, −10 °C, 89%; method b: NaNO₂...
  
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Beilstein J. Org. Chem. 2019, 15, 1347–1354, doi:10.3762/bjoc.15.134

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Efficient resolution of racemic crown-shaped cyclotriveratrylene derivatives and isolation and characterization of the intermediate saddle isomer

Sven Götz,
Andreas Schneider and
Arne Lützen

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Published 18 Jun 2019

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1. Graphical Abstract
2. Scheme 1: CTV and chiral CTV derivatives.
  
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3. Scheme 2: The two enantiomeric crown isomers of chiral CTV 1 and its saddle isomer 1-S.
  
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4. Scheme 3: Synthesis of CTV 1.
  
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5. Figure 1: a) Chromatogram of an analytical separation of (rac)-1 on a CHIRALPAK IB column as the stationary p...
  
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6. Figure 2: a) Chromatogram of the analytical separation of (rac)-1 (CHIRALPAK IB, 100% MeOH, 293 K, flow rate:...
  
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7. Figure 3: a) ¹H NMR spectrum of the neat crown isomers of (rac)-1 in CD₃OD (400 MHz, 298 K); b) ¹H NMR spectr...
  
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8. Figure 4: Chromatograms of the analytical separations (CHIRALPAK IB, acetonitrile/water 40:60, 293 K, flow ra...
  
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9. Figure 5: The mole fractions obtained in the racemization experiment plotted against the time, with black tri...
  
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Beilstein J. Org. Chem. 2019, 15, 1339–1346, doi:10.3762/bjoc.15.133

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Synthesis of dipolar molecular rotors as linkers for metal-organic frameworks

Sebastian Hamer,
Fynn Röhricht,
Marius Jakoby,
Ian A. Howard,
Xianghui Zhang,
Christian Näther and
Rainer Herges

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Published 18 Jun 2019

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1. Graphical Abstract
2. Figure 1: Interactions of a pair of dipolar rotors in different orientations. The axes of the rotors are para...
  
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3. Figure 2: Structures of molecular dipolar rotors/linker molecules 1–5.
  
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4. Scheme 1: General synthetic strategy to prepare the dipolar rotors 1–5.
  
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5. Scheme 2: Synthesis of 3,3'-(2,3-difluoro-1,4-phenylene)dipropiolic acid (1) starting with diiodination of 1,...
  
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6. Scheme 3: Synthesis of 3,3'-(5,6-Difluoro-2,1,3-benzothiadiazol-4,7-diyl)dipropiolic acid (2) and 3,3'-(5,6-D...
  
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7. Scheme 4: Synthesis of 3,3'-(5,6-dicyano-1,3-benzodioxole-4,7-diyl)dipropiolic acid (4) and 3,3'-(6,7-dicyano...
  
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Beilstein J. Org. Chem. 2019, 15, 1331–1338, doi:10.3762/bjoc.15.132

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Host–guest interactions between p-sulfonatocalix[4]arene and p-sulfonatothiacalix[4]arene and group IA, IIA and f-block metal cations: a DFT/SMD study

Valya K. Nikolova,
Cristina V. Kirkova,
Silvia E. Angelova and
Todor M. Dudev

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Published 17 Jun 2019

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1. Graphical Abstract
2. Scheme 1: Schematic representation of the structures of p-sulfonatocalix[4]arene (C[4]A) and p-sulfonatothiac...
  
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3. Figure 1: Optimized structures of negatively charged C[4]A and TC[4]A, presented in two projections: (A) side...
  
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4. Figure 2: Optimized structures of C[4]A complexes with Na⁺, Mg²⁺ and La³⁺.
  
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5. Figure 3: Optimized structures of C[4]A complexes with Rb⁺, Sr²⁺ and Lu³⁺.
  
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6. Figure 4: Optimized structures of TC[4]A complexes with Na⁺, Mg²⁺ and La³⁺.
  
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7. Figure 5: Optimized structures of TC[4]A complexes with Rb⁺, Sr²⁺ and Lu³⁺.
  
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8. Figure 6: M062X/6-31G(d,p) optimized structures of the [La(H₂O)₉]³⁺ cation, C[4]A host and C[4]A complex with...
  
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Beilstein J. Org. Chem. 2019, 15, 1321–1330, doi:10.3762/bjoc.15.131

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Mechanochemical Friedel–Crafts acylations

Mateja Đud,
Anamarija Briš,
Iva Jušinski,
Davor Gracin and
Davor Margetić

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Published 17 Jun 2019

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1. Graphical Abstract
2. Scheme 1: FCR of pyrene and phthalic anhydride.
  
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3. Scheme 2: Scope of acylation reagents in FCR under mechanochemical activation conditions and comparison with ...
  
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4. Scheme 3: Scope of aromatic substrates in FCR under mechanochemical activation conditions. ^aIsolated yields.
  
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5. Scheme 4: Mechanochemical regiodirected FCR of anthracene dimer and succinic anhydride.
  
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6. Scheme 5: Regioselectivity direction by protection of 9,10-anthracene ring positions.
  
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7. Scheme 6: Double FCR of phthaloyl chloride and aromatics.
  
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8. Figure 1: In situ Raman monitoring of reaction of phthalic anhydride with p-xylene.
  
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Beilstein J. Org. Chem. 2019, 15, 1313–1320, doi:10.3762/bjoc.15.130

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