A New Class of Ultrafast Photoswitchable Chromopeptides

Cordes, Thorben; Riesselmann, K.; Herre, S.; Rück‐Braun, K.

doi:10.1007/978-3-540-68781-8_176

Cited by 3 publications

(2 citation statements)

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“…On this topic we have recently reported a hemithioindigo photoswitch that can be operated using green and red light with a thermal half-life of the metastable E isomer of 30 days at 25 °C . Hemiindigo is structurally related to hemithioindigo − and consists of an indigo and a stilbene fragment sharing a common central double bond (Figure a). It is known as a chromophore for more than 100 years and was first described by Adolf von Baeyer in 1883 naming the compounds obtained from condensation of indoxylic acid and aldehydes “Indogenide” .…”

Section: Introductionmentioning

confidence: 99%

“…It is known as a chromophore for more than 100 years and was first described by Adolf von Baeyer in 1883 naming the compounds obtained from condensation of indoxylic acid and aldehydes “Indogenide” . Despite its facile synthesis, , established spectroscopic properties, − and relation to hemithioindigo − and aurone, − the photochemistry of hemiindigo is essentially unexplored especially with regard to applications as a photoswitch. As the absorption profile of unsubstituted hemiindigo resides partially in the visible part of the electromagnetic spectrum, the possibility of reversible double bond photoisomerization using exclusively visible light is highly tempting.…”

Section: Introductionmentioning

confidence: 99%

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Hemiindigo: Highly Bistable Photoswitching at the Biooptical Window

et al. 2017

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Hemiindigo is a long known chromophore that absorbs in the blue part of the spectrum but has almost completely been ignored as potential photoswitch. Herein we show how the absorption of hemiindigo is shifted to the red part of the visible spectrum and how nearly perfect photoswitching can be achieved using blue or green and red light. Five derivatives were investigated giving very high isomeric yields in both switching directions, i.e. >90% E isomer after irradiation with 470 to 530 nm light and 99% Z isomer with 590 up to 680 nm light. At the same time the thermal bistability is extraordinarily high leading to half-lives of the pure isomeric states of up to 83 years at 25 °C. The herein developed photoswitches show photochromism in the visible enabling the two isomeric states to be distinguished by the naked eye. Substituted hemiindigos therefore constitute extremely promising new photoswitches with excellent properties for applications in biology, chemistry, or material sciences.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Hemiindigo: Highly Bistable Photoswitching at the Biooptical Window

et al. 2017

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Oxidized Hemithioindigo Photoswitches—Influence of Oxidation State on (Photo)physical and Photochemical Properties

Köttner¹,

Schildhauer²,

Wiedbrauk³

et al. 2020

Chemistry A European J

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The photophysical and photochemical properties of sulfoxide and sulfone derivatives of hemithioindigo photoswitches are scrutinized and compared to the unoxidized parent chromophores. Oxidation results in significantly blue‐shifted absorptions and mostly reduction of photochromism while thermal stabilities of individual isomers remain largely unaltered. Effective photoswitching takes place at shorter wavelengths compared to parent hemithioindigos and high isomeric yields can be obtained reversibly in the respective photostationary states. Reversible solid‐state photoswitching is observed for a twisted sulfone derivative accompanied by visible color changes. These results establish oxidized hemithioindigo photoswitches as promising and versatile tools for robust light‐control of molecular behavior for a wide range of applications.

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