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3 article(s) from Hecht, Stefan

Oxidative and reductive cyclization in stiff dithienylethenes

Michael Kleinwächter,
Ellen Teichmann,
Lutz Grubert,
Martin Herder and
Stefan Hecht

Beilstein J. Org. Chem. 2018, 14, 2812–2821, doi:10.3762/bjoc.14.259

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Scheme 1: Combining double bond isomerization (E/Z) and cyclization/cycloreversion (Z/C) in three-state switc...

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Scheme 2: Overview of all sDTE and reference DTE compounds investigated in this study. The compound names ind...

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Figure 1: Cyclic voltammograms of sDTE₆₆-Me. a) Both E- (black line) and Z-isomer (blue dashed line) display ...

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Figure 2: Spectroelectrochemistry of sDTE₆₆-Me. Absorption changes during CV, insets showing the correspondin...

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Scheme 3: Proposed mechanism for the oxidative cyclization of sDTE₆₆-Me. Upon two-fold oxidation, both open i...

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Figure 3: Anodic peak potentials (E_p^a) of sDTEs and reference compounds in MeCN. Solid circles refer to the f...

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Figure 4: Cyclic voltammograms of sDTE₆₆-PhCN. The reduction of a) E-sDTE₆₆-PhCN (black line) is reversible, ...

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Figure 5: Cyclic voltammogram of DTE-PhFluorene. The ring-closed isomer (red dashed line) is formed both unde...

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Figure 6: Cyclic voltammograms of Me₂NPh-DTE-PhCN displaying separated one-electron anodic and cathodic waves...

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Scheme 4: Proposed mechanism to explain the observed selectivity of anodic and cathodic cyclization in sDTE₆₆...

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Published 09 Nov 2018

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Discrete multiporphyrin pseudorotaxane assemblies from di- and tetravalent porphyrin building blocks

Mirko Lohse,
Larissa K. S. von Krbek,
Sebastian Radunz,
Suresh Moorthy,
Christoph A. Schalley and
Stefan Hecht

Beilstein J. Org. Chem. 2015, 11, 748–762, doi:10.3762/bjoc.11.85

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Figure 1: Mono-, di-, and tetravalent axles A1, A2 and A4 and mono-, di-, and tetravalent hosts C1, C2 and C4...

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Scheme 1: Overview of the synthesis of the guests A2 and A4. a) Pyrrole (4), BF₃·Et₂O, DDQ, CHCl₃, rt; b) Zn(...

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Scheme 2: Synthesis of crown ether hosts C4 and C2: a) K₂CO₃, LiBr, 17, 2-[2-(2-chloroethoxy)ethoxy]ethanol, ...

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Figure 2: Schematic representation of the host–guests complexes. Top: complexes A2@C1₂, A4@C1₄, A1₂@C2 and A1₄...

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Figure 3: ¹H NMR (500 MHz, 298 K, CD₂Cl₂, 3 mM) of a) C1 (top), A2@C1₂ (middle) and A2 (bottom); b) C1 (top), ...

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Figure 4: ¹H NMR (500 MHz, 298 K, CD₂Cl₂, 3 mM) of a) C2 (top), A1₂@C2 (middle) and A1 (bottom) and b) C4 (to...

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Figure 5: Normalized UV–vis absorption spectra (CH₂Cl₂, 3 μM) of A2, A4, C2 and C4 and their complexes formed...

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Figure 6: ESI-Q-TOF-MS spectra (CH₂Cl₂, 0.2 µM; left hand side) and respective experimental and calculated is...

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Figure 7: ¹H NMR (500 MHz, 298 K, CD₂Cl₂, 1 mM) of a) C4 (top), A2₂@C4 (middle) and A2 (bottom); b) C2 (top), ...

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Figure 8: ¹H NMR (500 MHz, 298 K, CD₂Cl₂, 1 mM) of a) C4 (top), A4@C4 (middle) and A4 (bottom) and b) C2 (top...

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Figure 9: Normalized UV–vis absorption spectra (CH₂Cl₂, 2 μM) of the guests A2 and A4 (black), the hosts C2 a...

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Figure 10: ESI-Q-TOF-MS spectra (CH₂Cl₂, 0.2 µM; left hand side) and respective experimental and calculated is...

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Published 12 May 2015

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Design and synthesis of a photoswitchable guanidine catalyst

Philipp Viehmann and
Stefan Hecht

Beilstein J. Org. Chem. 2012, 8, 1825–1830, doi:10.3762/bjoc.8.209

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Scheme 1: Ring-opening polymerization (ROP) of lactide with TBD or the acyclic guanidine 1 as catalysts [16,18].

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Scheme 2: Illustration of a photoswitchable guanidine catalyst for the ROP of lactide and the corresponding t...

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Scheme 3: Synthesis of guanidine 2_E.

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Figure 1: ORTEP image of the single-crystal X-ray structure of guanidine 2_E, as well as a rotated close-up of...

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Figure 2: UV–vis spectra of guanidine 2 in acetonitrile, c = 3.9·10⁻⁵ mol/L. (a) E→Z isomerization with irrad...

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Scheme 4: Guanidine 11 as a catalyst in the ROP of rac-lactide (catalyst/initiator/monomer ratio = 10:1:100).

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Figure 3: Supposed intermediates resulting from either a cyclohexane-substituted guanidine (a) [18] or an aromati...

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Published 24 Oct 2012

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