Substituted Dibenzodiazocines: Rapid Synthesis and Photochemical Properties

Klockmann, Felix; Zender, Elena; Schanz, Tobias; Catapano, Claudia; Terfort, Andreas

doi:10.1021/acsomega.1c02524

Cited by 9 publications

(11 citation statements)

References 47 publications

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“…In 2021, Klockmann et al. reported the rapid synthesis and tuning of the photochemical properties of dibenzodiazocines via the substitution of different ring positions with different substituents 56 . Effects of substituents on photochemical properties of diazocine are less pronounced than that of unsubstituted AB.…”

Section: Main Contentsmentioning

confidence: 99%

Visible‐light‐switchable azobenzenes: Molecular design, supramolecular systems, and applications

et al. 2022

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Photocontrol of functional molecules and supramolecular systems provides promising directions for the development of innovative materials and technologies.Reversible photoswitches that can isomerize among different states play a vital role in such photoresponsive systems. However, the commonly used UV light for triggering the isomerization of photoswitches such as azobenzene (AB) has limited their applications in functional material systems because UV light penetrates poorly and causes damage to materials or biological tissues. Accordingly, tremendous endeavors have been devoted to the development of visible-light-switchable molecules and expand their new applications in various fields. Herein, we highlight the strategies of molecule design for visible-light-switchable ABs by discussing the effects of benzene substituents on the absorption spectrum. Based on this, visible-light-responsive supramolecular systems with metal-organic frames, cyclodextrins, nanoparticles, and biomolecules (DNAs, peptides, and proteins) are elaborated. Then, the light-responsive mechanical properties and their emerging applications in actuators, biological systems, information storage, energy storage, nonlinear optical devices, and photoswitchable adhesives are discussed. Finally, a summary of the challenges and perspective on visible-light-switchable ABs are outlined.

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Section: Main Contentsmentioning

confidence: 99%

Visible‐light‐switchable azobenzenes: Molecular design, supramolecular systems, and applications

et al. 2022

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“…General: Synthesis of monomers (BAzoDMA, AzoDMA, AzoDA, BCMA, BCA, and Bz6A) and photoisomerization behavior of BAzoDMA were described in Supporting Information. [46][47][48][49][50][51] NMR spectra were recorded on JEOL JNM-ECZ500R or Varian Mercury 400 spectrometers. DSC was performed on DSC-60 (Shimadzu).…”

Section: Methodsmentioning

confidence: 99%

Inducing Motions of Polymers in Liquid Nitrogen with Light

Ube,

Suka,

Ogikubo

et al. 2023

Advanced Materials

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Polymer materials that show macroscopic deformation in response to external stimuli are feasible for novel soft actuators including microactuators. Incorporation of photochromic moieties, such as azobenzenes, into polymer networks enables macroscopic deformation under irradiation with light through photoisomerization. Under cryogenic conditions, however, it has been difficult to induce macroscopic deformation as polymers lose their soft nature due to the severe restrictions of molecular motions. Here, activation of molecular motions and macroscopic deformation in liquid nitrogen only with light for polymers containing photochromic moieties is reported. Photoinduced bending of polymer networks with normal azobenzenes in liquid nitrogen is enabled by preliminary UV irradiation at room temperature to produce cis‐isomers. To realize photoinduced deformation directly in liquid nitrogen, polymer networks are functionalized with bridged azobenzenes, which exist as cis‐isomers in thermodynamic equilibrium. The films with bridged azobenzenes exhibit reversible photoisomerization and bending upon irradiation with light in liquid nitrogen without the need of preliminary irradiation, implying that the change in conformation of polymer chains can be isothermally induced even under cryogenic conditions. Achievement of flexible motions under cryogenic conditions through isothermal processes will greatly expand the operating temperature range of soft actuators.

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“…Diazocines also exhibit more efficient photoswitching using longer excitation wavelengths and possess higher quantum yields. [1][2][3][4][5][6][7][8][9][10][11][12][13] As a result, diazocines have found use in emerging elds, such as stimuli-responsive systems, [14][15][16][17][18][19] photoactuation, 20 and most notably, photopharmacology. [21][22][23][24][25][26][27][28] Unlike conventional azobenzene, whose triplet state properties have been investigated since the 1960s, 29 no studies on the triplet states of diazocine molecules have been published.…”

Section: Introductionmentioning

confidence: 99%

“…Diazocines also exhibit more efficient photoswitching using longer excitation wavelengths and possess higher quantum yields. 1–13 As a result, diazocines have found use in emerging fields, such as stimuli-responsive systems, 14–19 photoactuation, 20 and most notably, photopharmacology. 21–28…”

Section: Introductionmentioning

confidence: 99%