Fused Bis(hemi‐indigo): Broad‐Range Wavelength‐Independent Photoswitches

Berdnikova, Daria V.; Kriesche, Bernhard M.; Paululat, Thomas; Hofer, Thomas S.

doi:10.1002/chem.202202752

Cited by 10 publications

(2 citation statements)

References 26 publications

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“…For these reasons it can be stated that HIs are highly promising photoswitches, yet their full potential awaits to be explored. Currently different structural modifications of monoaryl-HIs are investigated to improve property design and applicability [50][51][52][53] . In light of the advances made with HTIs, diaryl-substitution would be a fundamentally important next step to significantly elevate the capacity of HI photoswitches (Fig.…”

mentioning

confidence: 99%

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

2023

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

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confidence: 99%

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

2023

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“…In 1968, Ross and Blanc for the first time applied the Fischer method to calculate the extinction coefficients and quantum yields of the forward and backward isomerization of N,N'-diacetylindigo (9a) in toluene without isolation of the Z-form [49]. The Fischer method remains relevant up to date and is frequently used for the characterization of the photoinduced forms of various indigoid photoswitches [50][51][52][53][54].…”

Section: Nn'-diacylindigosmentioning

confidence: 99%

Photochromic derivatives of indigo: historical overview of development, challenges and applications

Kaplan,

Seferoğlu,

Berdnikova

2024

Beilstein J. Org. Chem.

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The importance of indigo dyes is constantly increasing with the evolution of novel textile materials and photochromic material technologies. The aim of this review article is to provide a comprehensive overview of the development of photochromic indigo derivatives from the first report on the photochromic N,N'-diacetylindigo in 1954 until now. We begin with the list of historical milestones in the development of photochromic indigo derivatives. Further, we provide a brief description of the synthetic procedures utilised to obtain indigo and its derivatives, outline the structural peculiarities, photophysical and photochemical properties of indigo and proceed with the detailed discussion of the photochromic indigo derivatives. Finally, we highlight the photochromism of the structural isomers of indigo (isoindigo and indirubin) and provide an overview of prospective applications of indigo photoswitches.

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Solar Azo‐Switches for Effective E→Z Photoisomerization by Sunlight

Zhang,

Dong,

Bösking

et al. 2024

Angewandte Chemie

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Natural photoactive systems have evolved to harness broad‐spectrum light from solar radiation for critical functions such as light perception and photosynthetic energy conversion. Molecular photoswitches, which undergo structural changes upon light absorption, are artificial photoactive tools widely used for developing photoresponsive systems and converting light energy. However, photoswitches generally need to be activated by light of specific narrow wavelength ranges for effective photoconversion, which limits their ability to directly work under sunlight and to efficiently harvest solar energy. Here, focusing on azo‐switches—the most extensively studied photoswitches, we demonstrate effective solar E→Zphotoisomerization with photoconversions exceeding 80% under unfiltered sunlight. These sunlight‐driven azo‐switches are developed by rendering the absorption of E isomers overwhelmingly stronger than that of Z isomers across a broad ultraviolet to visible spectrum. This unusual type of spectral profile is realized by a simple yet highly adjustable molecular design strategy, enabling the fine‐tuning of spectral window that extends light absorption beyond 600 nm. Notably, back‐photoconversion can be achieved without impairing the forward solar isomerization, resulting in unique light‐reversible solar switches. Such exceptional solar chemistry of photoswitches provides unprecedented opportunities for developing sustainable light‐driven systems and efficient solar energy technologies.

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Fused Bis(hemi‐indigo): Broad‐Range Wavelength‐Independent Photoswitches

Cited by 10 publications

References 26 publications

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

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

Photochromic derivatives of indigo: historical overview of development, challenges and applications

Solar Azo‐Switches for Effective E→Z Photoisomerization by Sunlight

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