Photocontrol of Polar Aromatic Interactions by a Bis‐Hemithioindigo Based Helical Receptor

Guentner, Manuel; Uhl, Edgar; Mayer, Péter; Dube, Henry

doi:10.1002/chem.201604237

Cited by 41 publications

(29 citation statements)

References 78 publications

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“…More recent applications include digital information processing with a pH‐sensitive HTI molecule; a visible‐light‐responsive supramolecular receptor (HTI tweezers), the folding and affinity for aromatic guest molecules of which can be altered by irradiation and heating, or even light‐driven relocation of the guest between two such receptors …”

Section: Photoresponsive Materials and Nanostructuresmentioning

confidence: 99%

Recent Implementations of Molecular Photoswitches into Smart Materials and Biological Systems

Pianowski

2019

Chemistry A European J

286

226

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Light is a nearly ideal stimulus for molecular systems. It delivers information encoded in the form of wavelengths and their intensities with high precision in space and time. Light is a mild trigger that does not permanently contaminate targeted samples. Its energy can be reversibly transformed into molecular motion, polarity, or flexibility changes. This leads to sophisticated functions at the supramolecular and macroscopic levels, from light‐triggered nanomaterials to photocontrol over biological systems. New methods and molecular adapters of light are reported almost daily. Recently reported applications of photoresponsive systems, particularly azobenzenes, spiropyrans, diarylethenes, and indigoids, for smart materials and photocontrol of biological setups are described herein with the aim to demonstrate that the 21st century has become the Age of Enlightenment—“Le siècle des Lumières”—in molecular sciences.

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Section: Photoresponsive Materials and Nanostructuresmentioning

confidence: 99%

Recent Implementations of Molecular Photoswitches into Smart Materials and Biological Systems

Pianowski

2019

Chemistry A European J

286

226

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“…[5][6][7] Them ost convenient energy source is arguably light irradiation, which has led to the fastest motions realized so far. [5g] With this hemithioindigo [9] (HTI)-based molecular motor, we achieved very fast rotations (up to 1kHz at 20 8 8C);h owever, this also made full experimental access to the complete directional motion difficult. [5g] With this hemithioindigo [9] (HTI)-based molecular motor, we achieved very fast rotations (up to 1kHz at 20 8 8C);h owever, this also made full experimental access to the complete directional motion difficult.…”

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confidence: 99%

Direct Observation of Hemithioindigo‐Motor Unidirectionality

et al. 2017

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Hemithioindigo molecular motors undergo very fast unidirectional rotation upon irradiation with visible light, which has prevented a complete analysis of their working mechanism. In this work, we have considerably slowed down their motion by using a new synthesis for sterically hindered motor derivatives. This method allowed the first observation of all four intermediate states populated during rotation. The exact order in which each isomeric state is formed under irradiation conditions was elucidated using low temperature H NMR spectroscopy in conjunction with other analytical methods. At the same time, complete unidirectionality could also be directly shown. Access to slowly rotating hemithioindigo motors opens up a plethora of new applications for visible-light-induced unidirectional motions, especially in areas such as catalysis, smart materials, and supramolecular chemistry.

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“…In the research field of photoresponsive materials, indigoid chromophores, gained more and more importance in the last years due to their outstanding redshifted absorption. Hemithioindigo based peptide‐switches, protein inhibitors or molecular devices such as molecular calculators, motors, and receptors are interesting examples for shifting addressability at the molecular scale into the region of less energetic light. Very recently it was reported that di‐arylated indigos can be efficiently photoisomerized while possessing high barriers for thermal cis to trans isomerization .…”

Section: Introductionmentioning

confidence: 99%

Photoisomerization of Mono‐Arylated Indigo and Water‐Induced Acceleration of Thermal cis‐to‐trans Isomerization

2018

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Substituted indigo derivatives undergo photoisomerization of the central double bond if both nitrogen atoms are functionalized. Indigo itself however does not photoisomerize because of a competing and highly efficient excited‐state proton transfer. In this work, we show that also mono‐arylated indigo undergoes photoisomerization despite still possessing one nitrogen‐bound proton and the likely presence of a competing intramolecular excited‐state proton transfer. The two different isomers exhibit strongly different absorptions and therefore can be distinguished by the naked eye. Different to diaryl‐substituted indigo, thermal decay of the metastable cis isomers of mono‐arylated derivatives can be greatly accelerated by small amounts of water (by more than a factor of 300 for measured half‐lives). Such tunability is of high interest for applications that require quick and autonomous switching‐off of photoresponsive trigger units.

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Photocontrol of Polar Aromatic Interactions by a Bis‐Hemithioindigo Based Helical Receptor

Cited by 41 publications

References 78 publications

Recent Implementations of Molecular Photoswitches into Smart Materials and Biological Systems

Recent Implementations of Molecular Photoswitches into Smart Materials and Biological Systems

Direct Observation of Hemithioindigo‐Motor Unidirectionality

Photoisomerization of Mono‐Arylated Indigo and Water‐Induced Acceleration of Thermal cis‐to‐trans Isomerization

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