Recent advances in diarylethene-based multi-responsive molecular switches

Pu, Shouzhi; Sun, Qi; Fan, Congbin; Wang, Ren‐Jie

doi:10.1039/c6tc00110f

Cited by 211 publications

(110 citation statements)

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“…Alternatively, the photochromic mechanism can involve reversible photoinduced electron or H‐atom/proton transfer reactions. Furthermore, there are also synthetic molecular switches where the interconversion between the two states can be triggered by both light and other stimuli (such as pH), or is triggered by other stimuli than light altogether, such as temperature, pH or electric fields . Among the plethora of different classes of useful switches available today, Figure depicts some operated through E / Z photoisomerization, photocyclization or photoinduced H‐atom/proton transfer reactions, including azobenzene switches that tune the conductance of organic semiconductors, spiropyran switches that enable the fabrication of organic optical memory devices and salicylideneaniline switches that also can be driven by heat …”

Section: Introductionmentioning

confidence: 99%

Molecular Photoswitching Aided by Excited‐State Aromaticity

2018

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Central to the development of optoelectronic devices is the availability of efficient synthetic molecular photoswitches, the design of which is an arena where the evolving concept of excited‐state aromaticity (ESA) is yet to make a big impact. The aim of this minireview is to illustrate the potential of this concept to become a key tool for the future design of photoswitches. The paper starts with a discussion of challenges facing the use of photoswitches for applications and continues with an account of how the ESA concept has progressed since its inception. Then, following some brief remarks on computational modeling of photoswitches and ESA, the paper describes two different approaches to improve the quantum yields and response times of switches driven by E/Z photoisomerization or photoinduced H‐atom/proton transfer reactions through simple ESA considerations. It is our hope that these approaches, verified by quantum chemical calculations and molecular dynamics simulations, will help stimulate the application of the ESA concept as a general tool for designing more efficient photoswitches and other functional molecules used in optoelectronic devices.

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Section: Introductionmentioning

confidence: 99%

Molecular Photoswitching Aided by Excited‐State Aromaticity

2018

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“…7,8 The utility of photoswitchable materials can be further expanded if the materials are multiresponsive, that is, their optical response can be tuned via changes in environmental conditions (e.g., humidity, pH, presence of analytes). This offers a conceptual basis for photochromic sensors, 9,10 which have been developed from diarylethenes and spiropyrans, for example, for sensing anions, 11 amines, 12 and thiols. 13 For azobenzenes, to the best of our knowledge, such an isomerization kinetics based concept has not been demonstrated.…”

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confidence: 99%

Thermal Isomerization of Hydroxyazobenzenes as a Platform for Vapor Sensing

et al. 2018

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Photoisomerization of azobenzene derivatives is a versatile tool for devising light-responsive materials for a broad range of applications in photonics, robotics, microfabrication, and biomaterials science. Some applications rely on fast isomerization kinetics, while for others, bistable azobenzenes are preferred. However, solid-state materials where the isomerization kinetics depends on the environmental conditions have been largely overlooked. Herein, an approach to utilize the environmental sensitivity of isomerization kinetics is developed. It is demonstrated that thin polymer films containing hydroxyazobenzenes offer a conceptually novel platform for sensing hydrogen-bonding vapors in the environment. The concept is based on accelerating the thermal cis–trans isomerization rate through hydrogen-bond-catalyzed changes in the thermal isomerization pathway, which allows for devising a relative humidity sensor with high sensitivity and quick response to relative humidity changes. The approach is also applicable for detecting other hydrogen-bonding vapors such as methanol and ethanol. Employing isomerization kinetics of azobenzenes for vapor sensing opens new intriguing possibilities for using azobenzene molecules in the future.

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“…1 Because of the sharp difference in physical properties 2 such as optical, 3 electrochemical 4 and geometrical features 5 between the two isomers, photochromic compounds can be used to construct a variety of photoswitchable functional materials including fluorescence probes, 6 molecular logic gates, 7 optical data-storage devices 8 and photoresponsive assemblies. 9 Of the photochromic compounds reported, diarylethenes are viewed as one of the most promising candidates for photo-electronic applications due to their outstanding fatigue-resistance, 10 thermal stability 11 and rapid response towards light.…”

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confidence: 99%