Photochromic and Reductive Electrochemical Switching of a Dithiazolylethene with Large Redox Modulation
A new dipyridylthiazolylethene (1 a) and its dicationic analogue (2 a), with two N‐methylated pyridyl rings, have been synthesized and structurally characterized. Due to the N‐methylation of the pyridyl rings, 2 a displays not only very different photochromic properties, but also undergoes a reducti...
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| Published in: | Chemistry : a European journal Vol. 17; no. 7; pp. 2246 - 2255 |
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WILEY-VCH Verlag
11-02-2011
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| Abstract | A new dipyridylthiazolylethene (1 a) and its dicationic analogue (2 a), with two N‐methylated pyridyl rings, have been synthesized and structurally characterized. Due to the N‐methylation of the pyridyl rings, 2 a displays not only very different photochromic properties, but also undergoes a reductive ring‐closing reaction to generate its closed‐ring isomer 2 b. Careful electrochemical studies coupled with EPR spectroscopy show that this reductive ring‐closing reaction takes place when 2 a is two‐electron reduced. DFT calculations suggest that such a ground‐state electrocyclization is driven by a very large stabilization of the reduced closed‐ring isomer 2 b relative to the reduced open‐ring isomer 2 a. In addition, 2 b exhibits two successive and reversible one‐electron reductions at half‐wave potentials of 0.04 and −0.14 V versus SCE and a redox modulation as large as 1 V is achieved when passing from 2 a to 2 b.
An open‐and‐shut case: A dithiazolylethene capable of light‐activated and reductive electrochemical switching is designed. The conversion of the open‐ring form (OF2+) of the isomer to the closed‐ring form (CF2+; see picture) results in not only important changes in the electronic absorption and fluorescence properties, but also a redox shift as large as 1 V. |
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| AbstractList | A new dipyridylthiazolylethene (1a) and its dicationic analogue (2a), with two N-methylated pyridyl rings, have been synthesized and structurally characterized. Due to the N-methylation of the pyridyl rings, 2a displays not only very different photochromic properties, but also undergoes a reductive ring-closing reaction to generate its closed-ring isomer 2b. Careful electrochemical studies coupled with EPR spectroscopy show that this reductive ring-closing reaction takes place when 2a is two-electron reduced. DFT calculations suggest that such a ground-state electrocyclization is driven by a very large stabilization of the reduced closed-ring isomer 2b relative to the reduced open-ring isomer 2a. In addition, 2b exhibits two successive and reversible one-electron reductions at half-wave potentials of 0.04 and -0.14V versus SCE and a redox modulation as large as 1V is achieved when passing from 2a to 2b. A new dipyridylthiazolylethene (1a) and its dicationic analogue (2a), with two N-methylated pyridyl rings, have been synthesized and structurally characterized. Due to the N-methylation of the pyridyl rings, 2 a displays not only very different photochromic properties, but also undergoes a reductive ring-closing reaction to generate its closed-ring isomer 2b. Careful electrochemical studies coupled with EPR spectroscopy show that this reductive ring-closing reaction takes place when 2a is two-electron reduced. DFT calculations suggest that such a ground-state electrocyclization is driven by a very large stabilization of the reduced closed-ring isomer 2b relative to the reduced open-ring isomer 2a. In addition, 2b exhibits two successive and reversible one-electron reductions at half-wave potentials of 0.04 and -0.14 V versus SCE and a redox modulation as large as 1 V is achieved when passing from 2a to 2b. A new dipyridylthiazolylethene ( 1 a ) and its dicationic analogue ( 2 a ), with two N‐methylated pyridyl rings, have been synthesized and structurally characterized. Due to the N‐methylation of the pyridyl rings, 2 a displays not only very different photochromic properties, but also undergoes a reductive ring‐closing reaction to generate its closed‐ring isomer 2 b . Careful electrochemical studies coupled with EPR spectroscopy show that this reductive ring‐closing reaction takes place when 2 a is two‐electron reduced. DFT calculations suggest that such a ground‐state electrocyclization is driven by a very large stabilization of the reduced closed‐ring isomer 2 b relative to the reduced open‐ring isomer 2 a . In addition, 2 b exhibits two successive and reversible one‐electron reductions at half‐wave potentials of 0.04 and −0.14 V versus SCE and a redox modulation as large as 1 V is achieved when passing from 2 a to 2 b . A new dipyridylthiazolylethene (1 a) and its dicationic analogue (2 a), with two N‐methylated pyridyl rings, have been synthesized and structurally characterized. Due to the N‐methylation of the pyridyl rings, 2 a displays not only very different photochromic properties, but also undergoes a reductive ring‐closing reaction to generate its closed‐ring isomer 2 b. Careful electrochemical studies coupled with EPR spectroscopy show that this reductive ring‐closing reaction takes place when 2 a is two‐electron reduced. DFT calculations suggest that such a ground‐state electrocyclization is driven by a very large stabilization of the reduced closed‐ring isomer 2 b relative to the reduced open‐ring isomer 2 a. In addition, 2 b exhibits two successive and reversible one‐electron reductions at half‐wave potentials of 0.04 and −0.14 V versus SCE and a redox modulation as large as 1 V is achieved when passing from 2 a to 2 b. An open‐and‐shut case: A dithiazolylethene capable of light‐activated and reductive electrochemical switching is designed. The conversion of the open‐ring form (OF2+) of the isomer to the closed‐ring form (CF2+; see picture) results in not only important changes in the electronic absorption and fluorescence properties, but also a redox shift as large as 1 V. |
| Author | Métivier, Rémi Maurel, François Midelton, Stéphanie Yu, Pei Anxolabéhère-Mallart, Elodie Léaustic, Anne Guillot, Régis Nakatani, Keitaro |
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| Snippet | A new dipyridylthiazolylethene (1 a) and its dicationic analogue (2 a), with two N‐methylated pyridyl rings, have been synthesized and structurally... A new dipyridylthiazolylethene (1a) and its dicationic analogue (2a), with two N-methylated pyridyl rings, have been synthesized and structurally... A new dipyridylthiazolylethene ( 1 a ) and its dicationic analogue ( 2 a ), with two N‐methylated pyridyl rings, have been synthesized and structurally... |
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| SubjectTerms | Chemical reactions Chemistry density functional calculations Displays electrochemistry Isomers Joining Mathematical analysis Modulation photochromism redox chemistry reduction Stabilization Switching |
| Title | Photochromic and Reductive Electrochemical Switching of a Dithiazolylethene with Large Redox Modulation |
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