A complementary pair of enantioselective switchable organocatalysts

Bo, Guillaume De; Leigh, David A.; McTernan, Charlie T.; Wang, Shoufeng

doi:10.1039/c7sc02462b

Cited by 47 publications

(56 citation statements)

References 67 publications

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“…The Z isomer of acylhydrazones, usually disfavored, can be stabilized with properly introduced hydrogen bonds . This effect was used for pyridyl acylhydrazones, in switchable cinchona‐derived enantioselective organocatalysts, as well as in the first photoswitchable heteroditopic ion‐pair receptor in which both cation and anion binding sites were simultaneously and reversibly switched …”

Section: Molecular Photoswitchesmentioning

confidence: 99%

Recent Implementations of Molecular Photoswitches into Smart Materials and Biological Systems

Pianowski

2019

Chemistry A European J

287

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: Molecular Photoswitchesmentioning

confidence: 99%

Recent Implementations of Molecular Photoswitches into Smart Materials and Biological Systems

Pianowski

2019

Chemistry A European J

287

226

View full text Add to dashboard Cite

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“…In addition, the above organocatalyst can be rendered inactive again by the addition of acids to protonate the newly formed amine species. Thus, this work successfully introduces rotaxane‐based switchable catalysts and provides a basis for their further fabrication …”

Section: Microscale Applicationsmentioning

confidence: 99%

Driving Smart Molecular Systems by Artificial Molecular Machines

Shi

Zhang

Tian

et al. 2020

Advanced Intelligent Systems

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Biomolecular machines are widely present in nature, especially in complex living organisms, and are involved in important biological processes. Inspired by nature and increasingly mature synthetic technologies, a series of artificial molecular machines (AMMs) that exhibit similar processes and functions as biomolecular counterparts have been developed, and to date, some dramatic achievements have been obtained. Herein, the use of AMMs in smart systems and materials with controllable regulations and interesting functions are summarized, presenting the specific micro‐ to macroscale applications in solid surface modification, transmembrane transport, smart catalysts, liquid crystals, artificial molecular muscles, and stimuli‐responsive polymers. The challenges of developing novel complex AMMs with intelligent functions are discussed, and some potential solutions are proposed.

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“…A different solution to the problem of controlling multiple molecular processes with external signals has just very recently been conceptualized by the group of David Leigh 50 . Therein it was proposed to affect multiple events by the same signal to drastically reduce the overall triggering needed.…”

Section: Introductionmentioning

confidence: 99%

Simultaneous complementary photoswitching of hemithioindigo tweezers for dynamic guest relocalization

et al. 2018

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Remote control of complex molecular behavior and function is one key problem in modern chemistry. Using light signaling for this purpose has many advantages, however the integration of different photo processes into a wholesome yet complex system is highly challenging. Here we report an alternative approach to increase complexity of light control-simultaneous complementary photoswitching-in which spectral overlap is used as an advantage to drastically reduce the signaling needed for controlling multipart supramolecular assemblies. Two photoswitchable molecular tweezers respond to the same light signals with opposite changes in their binding affinities. In this way the configuration of two host tweezers and ultimately the dynamic relocation of a guest molecule can be trigged by only one signal reversibly in the same solution. This approach should provide a powerful tool for the construction of sophisticated, integrated, and multi-responsive smart molecular systems in any application driven field of chemistry.

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A complementary pair of enantioselective switchable organocatalysts

Abstract: A pair of enantioselective switchable bifunctional catalysts are shown to promote a range of conjugate addition reactions in up to 95 : 5 e.r. and 95% conversion.

Cited by 47 publications

References 67 publications

Recent Implementations of Molecular Photoswitches into Smart Materials and Biological Systems

Recent Implementations of Molecular Photoswitches into Smart Materials and Biological Systems

Driving Smart Molecular Systems by Artificial Molecular Machines

Simultaneous complementary photoswitching of hemithioindigo tweezers for dynamic guest relocalization

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