A monomolecular platform with varying gated photochromism

Li, Yuezheng; Chen, Xuanying; Weng, Taoyu; Yang, Jufang; Zhao, Chunrui; Wu, Bin; Zhang, Man; Zhu, Liangliang; Zou, Qi

doi:10.1039/d0ra08214g

Cited by 8 publications

(7 citation statements)

References 39 publications

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“…In 1952, Hirshberg et al discovered that spiropyrans can undergo reversible color change under light irradiation, which is called photochromism, that is, photochromic phenomenon. 1 Photochromic materials are a new type of functional materials developed in recent years, 2 and play an increasingly important role in daily life, industry and military fields, which can be used to make photochromic accessories, 3 ultraviolet sensors, 4 optical storage devices, 5 recording media, 6 nonlinear optical materials 7 and so on. As the superior electron acceptors of photochromic materials, viologen compounds, defined as N , N ′-bisubstituted-4,4′-bipyridinium dications, are one of the first choices for the construction of redox photochromic complexes due to the reason that they can be easily photoreduced accompanied by obvious color changes.…”

Section: Introductionmentioning

confidence: 99%

The modulation effect of pi–pi interactions on the electronic and photochromic properties of viologen complexes containing N,N′-bis(carboxyethyl)-4,4′-bipyridinium

Zhao

Liu

2021

RSC Adv.

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Section: Introductionmentioning

confidence: 99%

The modulation effect of pi–pi interactions on the electronic and photochromic properties of viologen complexes containing N,N′-bis(carboxyethyl)-4,4′-bipyridinium

Zhao

Liu

2021

RSC Adv.

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“…In addition to light of different wavelengths, various external stimuli, including intramolecular hydrogen bonds, [ 156 ] multiphotonic excitation, [ 48,49 ] acid/base changes, [ 157 ] oxidation/reduction, [ 127,158 ] chemical reactions, [ 159 ] temperature changes, [ 145 ] electrochemical changes, [ 160 ] and chemical species such as ions, [ 121b,134,161 ] can also be used as input signals to change the output state or gating properties of a gate control switch containing DAE, with the changes usually reflected by a significant shift in color. Additional stimulus‐responsive units can be used to covalently modify DAE cores, [ 9c,160 ] introduce more responsive sites that allow modification in DAE‐gated switches, and design supramolecular assembly systems.…”

Section: Changes In the Physical And Chemical Properties Of Daementioning

confidence: 99%

“…Zou et al. [ 161 ] used Schiff base groups to modify the DAE core and prepared a DAE derivative, DTEP, as a gate switch. Their single‐molecule platform acted as a molecular logic device and responded to specific stimuli.…”

Section: Changes In the Physical And Chemical Properties Of Daementioning

confidence: 99%

Future‐Oriented Advanced Diarylethene Photoswitches: From Molecular Design to Spontaneous Assembly Systems

et al. 2022

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cycloreversion of DAE under light irradiation produces many exciting functional effects, such as changes in photophysical and photochemical properties, [12] changes in the shape or mechanical properties of the solid, [13] electrical conductivity, [7b,14] and the generation of reactive oxygen species (ROS). [15] This type of photochromic compound can be considered a stilbene derivative. At this time, the most widely known and systematically studied DAE derivative structure contains two aryl groups and a benzene ring (usually two identical or different thiophene units with low aromatic stabilization energy [16] ) and a five-membered ring of perfluorocyclopentene and cyclopentene units [17] where the ethene bridge is located, which significantly improve photochromism. [18] In essence, the DAE photoisomerization process is a reversible electrocyclic reaction of the central 6π-electron systems. [2] Under light irradiation, DAE can rapidly and reversibly transform between its open and closed forms, and that transformation is accompanied by a color change caused by a change in the π-conjugation distribution. [2] The important thing is that the colorless opened-and colored closed-ring isomers are both thermally stable; that is, cyclization and cycloreversion do not proceed spontaneously in the dark; they need to be driven by external light irradiation at specific wavelengths. [2,19] Compared with classic lightresponsive molecules such as azobenzene, [20] the light intensity required to drive the isomerization of DAE is relatively low. Moreover, even after multiple cycles, the photochromic performance does not show significant fatigue in either the solution or solid state. [2,18b,21] DAE research to this point can be roughly divided into three stages in chronological order: early exploration of DAE's molecular structure and theory, nearly two decades of purpose-oriented molecular structure modification research, and about ten years of research into practical applications of DAE in assembly systems. Research before about 2000 focused mainly on developing more abundant DAE-derivative structures and advancing the systematic understanding of DAE's physical and chemical properties and switching performance. To regulate its switching performance and give it new functionality, many strategies for modifying the ethene bridge and aryl groups of DAE have been proposed. [22] In the first two research stages, the mechanisms and structural modification of DAE isomerization were thoroughly and systematically explored, and countless important Diarylethene (DAE) photoswitch is a new and promising family of photochromic molecules and has shown superior performance as a smart trigger in stimulus-responsive materials. During the past few decades, the DAE family has achieved a leap from simple molecules to functional molecules and developed toward validity as a universal switching building block. In recent years, the introduction of DAE into an assembly system has been an attractive strategy that enables the photochromic behavior of the b...

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Section: Gating Strategies Of Daesmentioning

confidence: 99%

“…Notably, their photoreactiv-ity can be suppressed when selectively complexed with Ni 2+ and Cu 2+ , while as expected, the dissociation by EDTA triggers the cyclization process. [51,52] Wang et al introduced guanidine to a Schiff base modified DAE to form a star-shaped molecule 50o. [53] Similarly, it exhibits typical photochromic behavior in the open-ring isomer.…”

Section: Ions Gatedmentioning

confidence: 99%

Recent Progress of Gated Diarylethenes: Strategies, Mechanism, and Applications

Shi,

Zhu,

Guo

et al. 2023

Advanced Optical Materials

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Diarylethenes (DAEs) exhibiting photochromic behavior have emerged as a popular research topic owing to their superior thermal stability, rapid photo‐responsiveness, robust fatigue resistance, and remarkable solution/solid‐state photochromic properties. However, the overlapped reading wavelength and absorption of DAEs can lead to a partial photochromic reaction, resulting in destructive readout that erodes pre‐existing information in memory and data processing. To address this issue, researchers have implemented a range of strategies, including gated reactivity, infrared (IR) absorption, and Raman scattering readout. Among them, gating functions as a “key” or “lock” to regulate the photochromic reactivity through external stimuli, such as reactions, chemicals, additional photons, or heat, making it a viable solution. This review presents a summary of recent developments in gated DAEs, with a particular focus on gating strategies and principles, including modulation of the 1,3,5‐hexatriene moiety and molecular conformation, and regulation of activation energy. Additionally, the challenges and opportunities of gated DAEs systems for future non‐destructive readout and functional materials are also discussed.

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A monomolecular platform with varying gated photochromism

Abstract: A strategy to realize varying degrees of gated photochromic properties by coordinating with different metal ions within one unimolecular system was devised to achieve the construction of a logic circuit for multi-functional molecular switching.

Cited by 8 publications

References 39 publications

The modulation effect of pi–pi interactions on the electronic and photochromic properties of viologen complexes containing N,N′-bis(carboxyethyl)-4,4′-bipyridinium

The modulation effect of pi–pi interactions on the electronic and photochromic properties of viologen complexes containing N,N′-bis(carboxyethyl)-4,4′-bipyridinium

Future‐Oriented Advanced Diarylethene Photoswitches: From Molecular Design to Spontaneous Assembly Systems

Recent Progress of Gated Diarylethenes: Strategies, Mechanism, and Applications

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