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1 article(s) from Tepper, Christina

Toward unidirectional switches: 2-(2-Hydroxyphenyl)pyridine and 2-(2-methoxyphenyl)pyridine derivatives as pH-triggered pivots

Christina Tepper and
Gebhard Haberhauer

Beilstein J. Org. Chem. 2012, 8, 977–985, doi:10.3762/bjoc.8.110

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Scheme 1: Principle of the switching mechanism of 2-(2-hydroxyphenyl)pyridine (2) and 2-(2-methoxyphenyl)pyri...

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Figure 1: (a) Calculated energy profiles of the pyridine derivatives 1 (blue) and 2 (red) in relation to the ...

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Scheme 2: Principle of the switching mechanism of 2-(2-hydroxyphenyl)-3-methylpyridine (6) and 2-(2-methoxyph...

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Figure 2: (a) Calculated energy profiles of the 3-methylpyridine derivatives 5 (blue) and 6 (red) in relation...

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Figure 3: UV spectral change of phenolate 5 (blue) in dichloromethane (c = 5.6 × 10⁻⁵ M) at 20 °C upon additi...

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Figure 4: UV spectral change of 3-methylpyridine 7 (blue) in dichloromethane (c = 5.6 × 10^–5 M) at 20 °C upon...

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Figure 5: HOMO (left) and LUMO (right) of the 3-methylpyridine 7 calculated by using B3LYP/6-31G*.

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Scheme 3: Synthesis of the methoxyphenylpyridine switch 10 and the hydroxypyridine switch 12; reaction condit...

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Figure 6: (a) CD spectral change of pyridine switch 13 (blue) in dichloromethane (c = 5.6 × 10^–5 M) at 20 °C ...

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Figure 7: (a) CD spectral change of pyridine switch 10 (blue) in dichloromethane (c = 5.6 × 10^–5 M) at 20 °C ...

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Published 29 Jun 2012

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