Diaryl-hemiindigos as visible light, pH, and heat responsive four-state switches and application in photochromic transparent polymers DOI Creative Commons

Maximilian Sacherer,

Frank Hampel, Henry Dube

et al.

Nature Communications, Journal Year: 2023, Volume and Issue: 14(1)

Published: July 20, 2023

Photoswitches are indispensable tools for responsive chemical nanosystems and used today in almost all areas of the natural sciences. Hemiindigo (HI) derivatives have recently been introduced as potent photoswitches, but their full applicability has hampered by limited possibilities functionalization structural modification. Here we report on a short easy to diversify synthesis yielding diaryl-HIs bearing one additional aromatic residue at central double bond. The resulting chromophores offer an advantageous property profile combining red-light responsiveness, high thermal bistability, strong isomer accumulations both switching directions, photochromism, tunable acid gating. With this progress, broader realm becomes accessible HI which can now be synthetically tailored advanced future applications, e.g., research molecular machines switches, studies photoisomerization mechanisms, or generation smart addressable materials. To showcase potential these distinct light-responsive tools, demonstrate four-state switching, fueling, reversible inscription into transparent polymers using green red light well acid/base stimuli, addition comprehensive photochemical study compounds.

Language: Английский

The evolution of spiropyran: fundamentals and progress of an extraordinarily versatile photochrome DOI Creative Commons
Luuk Kortekaas, Wesley R. Browne

Chemical Society Reviews, Journal Year: 2019, Volume and Issue: 48(12), P. 3406 - 3424

Published: Jan. 1, 2019

Spiropyrans have played a pivotal role in the emergence of field chromism following their discovery early 20th century, with almost ubiquitous use materials applications especially since photochromism was discovered 1952. Their versatility continues to lend them application increasingly diverse fields not least due recent discoveries properties that expanded utility extensively. This review provides an overview rich history and highlights contemporary relevance spiropyrans.

Language: Английский

Citations

578
Photo- and Redox-Driven Artificial Molecular Motors DOI Creative Commons
Massimo Baroncini, Serena Silvi, Alberto Credi

et al.

Chemical Reviews, Journal Year: 2019, Volume and Issue: 120(1), P. 200 - 268

Published: Aug. 15, 2019

Directed motion at the nanoscale is a central attribute of life, and chemically driven motor proteins are nature’s choice to accomplish it. Motivated inspired by such bionanodevices, in past few decades chemists have developed artificial prototypes molecular motors, namely, multicomponent synthetic species that exhibit directionally controlled, stimuli-induced movements their parts. In this context, photonic redox stimuli represent highly appealing modes activation, particularly from technological viewpoint. Here we describe evolution field photo- redox-driven provide comprehensive review work published 5 years. After an analysis general principles govern controlled directed movement scale, fundamental photochemical processes can enable its realization. The main classes light- motors illustrated, with particular focus on recent designs, thorough description functions performed these kinds devices according literature reports presented. Limitations, challenges, future perspectives critically discussed.

Language: Английский

Citations

454
Supramolecular chiroptical switches DOI
Li Zhang, Han‐Xiao Wang, Shuai Li

et al.

Chemical Society Reviews, Journal Year: 2020, Volume and Issue: 49(24), P. 9095 - 9120

Published: Jan. 1, 2020

Recent progress in chiroptical switches including on/off, amplification, and inversion of the chiral signals such as ECD CPL supramolecular assemblies is shown.

Language: Английский

Citations

305
Molecular photoswitches in aqueous environments DOI Creative Commons
Jana Volarić, Wiktor Szymański, Nadja A. Simeth

et al.

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(22), P. 12377 - 12449

Published: Jan. 1, 2021

Molecular photoswitches are inherently lipophilic and do not spontaneously dissolve in water. We describe the effect of water on photochemical properties strategies to solubilize organic apply them aqueous media.

Language: Английский

Citations

282
Fluorescent Photochromic α‐Cyanodiarylethene Molecular Switches: An Emerging and Promising Class of Functional Diarylethene DOI
Siyang Lin,

Karla G. Gutierrez‐Cuevas,

Xinfang Zhang

et al.

Advanced Functional Materials, Journal Year: 2020, Volume and Issue: 31(7)

Published: Nov. 3, 2020

Abstract Fluorescent photochromic molecules that exhibit distinct light‐triggered changes in their emission colors are highly desirable for the fabrication of smart soft materials and advanced photonic devices. α‐Cyanodiarylethenes, is, α‐cyano‐functionalized diarylethenes, as alternative “non‐azo” Z/E molecular switches, popular choices due to unique characteristics such aggregation‐induced or aggregation‐induced‐enhanced behavior self‐assembled states, visible fluorescence during photoisomerization. In recent years, development fluorescent α‐cyanodiarylethene‐based compounds including α‐cyanostilbenes, dicyanodistyrylbenzenes, diaryldicyanoethenes, has mainly focused on design, photochemical photophysical solution, matter technologies. this review, significant achievements light‐responsive systems based photoisomerization α‐cyanodiarylethene switches span range from liquid crystals gels finally nanostructures, highlighted. The constructed find use a plethora areas, display, sensing, encrypting, actuating, biomedical imaging applications, among others. review concludes with brief perspective some major challenges opportunities future materials.

Language: Английский

Citations

185
Dissipative Self-Assembly: Fueling with Chemicals versus Light DOI Creative Commons
Maren Weißenfels, Julius Gemen,

Rafał Klajn

et al.

Chem, Journal Year: 2021, Volume and Issue: 7(1), P. 23 - 37

Published: Jan. 1, 2021

Language: Английский

Citations

173
Smart Photochromic Materials Triggered with Visible Light DOI
Anna‐Lena Leistner, Zbigniew Pianowski

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(19)

Published: Feb. 26, 2022

Abstract Molecular photoswitches reversibly convert the energy of light into a variety structural changes at molecular level. They can be integrated smart materials with broad range applicability. While most photochromic systems require UV for activation, application operational entirely within visible or NIR brings considerable benefits, such as biocompatibility, better penetration through material, propelling sunlight, possibility to design dual that are mutually activated frequencies two distinct functions. In this Review, we discuss relevant classes photoswitches, and demonstrate selection polymers, gels, porous materials, surfaces, energy‐storing other triggered light.

Language: Английский

Citations

91
Photoswitchable diarylethenes: From molecular structures to biological applications DOI
Ziyong Li,

Xiaoyan Zeng,

Caimin Gao

et al.

Coordination Chemistry Reviews, Journal Year: 2023, Volume and Issue: 497, P. 215451 - 215451

Published: Sept. 18, 2023

Language: Английский

Citations

76
Visible light-responsive materials: the (photo)chemistry and applications of donor–acceptor Stenhouse adducts in polymer science DOI Creative Commons
Michèle Clerc, Sara Sandlass, Omar Rifaie‐Graham

et al.

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 52(23), P. 8245 - 8294

Published: Jan. 1, 2023

Donor-acceptor Stenhouse adduct (DASA) photoswitches have gained a lot of attention since their discovery in 2014. Their negative photochromism, visible light absorbance, synthetic tunability, and the large property changes between photoisomers make them attractive candidates over other commonly used for use materials with responsive or adaptive properties. The development such translation into advanced technologies continues to widely impact forefront research, DASAs thus attracted considerable interest field visible-light molecular switches dynamic materials. Despite this interest, there been challenges understanding complex behavior context both small molecule studies Moreover, incorporation polymers can be challenging due incompatibility conditions most common polymerization techniques. In review, therefore, we examine critically discuss recent developments DASA-containing polymers, aiming at providing better interplay properties constituents (matrix photoswitch). first part summarizes current DASA design switching second section discusses strategies materials, methods studying We also emerging applications polymeric ranging from light-responsive drug delivery systems, photothermal actuators, sensors photoswitchable surfaces. Last, summarize venture on steps required explore novel systems expand functional application opportunities polymers.

Language: Английский

Citations

54
Phenylazothiazoles as Visible-Light Photoswitches DOI
Runze Lin, P. K. Hashim, Saugata Sahu

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(16), P. 9072 - 9080

Published: April 12, 2023

A novel class of photoswitches based on a phenylazothiazole scaffold that undergoes reversible isomerization under visible-light irradiation is reported. The photoswitch, which comprises thiazole heteroaryl segment directly connected to phenyl azo chromophore, has very different spectral characteristics, such as redshifted absorption maximum wavelength and well-separated bands the trans cis isomers, than conventional azobenzene other compounds. Substituents at ortho para positions ring photoswitch resulted in further shift longer wavelengths up 525 nm with small thermal stability compensation. These showed excellent photostationary distributions half-lives 7.2 h, reductant stability. X-ray crystal structure analysis revealed isomers exhibited planar geometry T-shaped orthogonal geometry. Detailed ab initio calculations demonstrated plausible electronic transitions energy barriers, were consistent experimental observations. fundamental design principles elucidated this study will aid development wide variety for photopharmacological applications.

Language: Английский

Citations

50