Tautomerizable Azophenol Dyes: Cornerstones for Advanced Light‐Responsive Materials

García-Amorós, Jaume; Velasco, Dolores

doi:10.1002/9783527695713.ch11

Cited by 6 publications

(2 citation statements)

References 93 publications

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“…It is also included among the most promising photochemically driven molecular motors [ 28 ]. The kinetics and mechanism for the photochromism of hydroxyazobenzenes have been the subject of many theoretical and experimental investigations [ 29 , 30 ]. The presence of a hydrogen bond between the hydroxyl and azo groups favors the formation of a tautomeric hydrazone-like intermediate with a partial breaking of the N=N bond.…”

Section: Introductionmentioning

confidence: 99%

The Versatile Photo-Thermal Behaviour of a 2-Hydroxyazobenzene

et al. 2023

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Photochromic compounds are employed in implementing neuron surrogates. They will boost the development of neuromorphic engineering in wetware. In this work, the photochromic behaviours of (E)-3,4,6-trichloro-2-(p-diazenil)-phenol (t-DZH) and its conjugated phenoxide base (t-DZ) have been investigated experimentally in three different media: (1) pure acetonitrile, (2) in water and acetonitrile mixed in a 1/1 volume ratio, and (3) in an aqueous micellar solution of 3-(N,N-Dimethylmyristylammonio)propanesulfonate (SB3-14). The analysis of the spectral and kinetic features of t-DZH and t-DZ has been supported by quantum-mechanical DFT calculations, the maximum entropy method, and the determination of their colourability (C). The versatility of t-DZH and t-DZ makes them promising molecular probes of micro-environments and potential ingredients of photochemical oscillators required for implementing pacemaker neurons capable of communicating through optical signals in wetware.

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Section: Introductionmentioning

confidence: 99%

The Versatile Photo-Thermal Behaviour of a 2-Hydroxyazobenzene

et al. 2023

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“…Indeed, the integration of azo dyes into host LCs of different nature has already allowed the access to a diversity of applications, from information and display technology to artificial actuation to intelligent wearables. − Generally, photo-irradiation with UV light transforms trans -azobenzenes into their metastable cis form; illumination with visible light or spontaneous thermal relaxation returns the system to its thermodynamically stable trans isomer . The lifetime of the cis form spans from several months (even years) to a few picoseconds, depending on the molecular structure of azobenzene; − furthermore, the solvent and general environment in which it is embedded also plays a determinant role. − Consequently, a complete understanding of the mechanism actuating for the thermal back reaction is crucial to control the rate of the process and, in turn, to design novel azobenzene-based photoactive liquid-crystalline materials with programmed properties and abilities.…”

Section: Introductionmentioning

confidence: 99%

High-Pressure Kinetics of Azo Dyes in Nematic Liquid Crystals

2019

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The introduction of organic photochromes into nematic liquid crystals (LCs) enables the modulation of their macroscopic properties and gives rise to unique applications. In particular, azo compounds are the dyes of common choice for this task because of their clean and reversible isomerization. In this context, gaining a good insight into how the LC medium influences the kinetics of the isomerization process is essential to develop novel liquid-crystalline materials with specific capabilities. Herein, we report the measure for the first time of the pressure activation parameters for the cis-to-trans thermal isomerization reaction of azo dyes in this self-organized state of condensed matter. For this purpose, a novel setup has been developed, which can also be utilized for highly lightabsorbing solutions. Initially, the mechanism of the thermal back reaction in the isotropic phase of the LC has been confirmed and compared with that observed in standard solvents (ΔV ⧧ ≈ 0). Further increase in pressure or decrease in temperature leads to the measure of the pressure dependence of such cis-to-trans thermal isomerization process in the nematic phase of the LC. This dependence, showing an increase in the rate with pressure, clearly does not directly relate to the activation volume of the motion of the dye but to the increase in the order of the LC.

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En Routeto Ultrafast Switchable Azo Dyes

García-Amorós

Velasco

2022

Molecular Photoswitches

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Tautomerizable Azophenol Dyes: Cornerstones for Advanced Light‐Responsive Materials

Cited by 6 publications

References 93 publications

The Versatile Photo-Thermal Behaviour of a 2-Hydroxyazobenzene

The Versatile Photo-Thermal Behaviour of a 2-Hydroxyazobenzene

High-Pressure Kinetics of Azo Dyes in Nematic Liquid Crystals

En Routeto Ultrafast Switchable Azo Dyes

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