The solvent-dependent isomerization dynamics of 4-(dimethylamino)azobenzene (DMAAB) studied by subpicosecond pump–probe spectroscopy

Mayer, Steven G.; Thomsen, Carsten; Philpott, Matthew P.; Reid, Philip J.

doi:10.1016/s0009-2614(99)01151-3

Cited by 34 publications

(19 citation statements)

References 18 publications

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“…There is ar ich literature treatingb oth the photoinduced properties of azobenzenes in solution [7][8][9][10][11] as well as in polymer films and liquid crystals. [14,[16][17][18][19][20][21][22][23][24][27][28][29][30][31] Much less work has been performed on pure solids.…”

Section: Discussionmentioning

confidence: 99%

“…[5,6] It has been the object of severalf undamental photophysical studies and reviews. [7][8][9][10][11][12][13] Furthermore,i t has been shown that azobenzene derivatives can be used as photoactuated switches in nanoscale devices. [14][15][16][17][18][19][20][21][22][23][24] Natanshon et al [19,20] showedthat polymers containing azobenzene deriva-tives could be used for reversible opticals torage.…”

Section: Introductionmentioning

confidence: 99%

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Photoinduced Trans‐to‐cis Phase Transition of Polycrystalline Azobenzene at Low Irradiance Occurs in the Solid State

et al. 2017

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The ability to produce large-scale, reversible structural changes in a variety of materials by photoexcitation of a wide variety of azobenzene derivatives has been recognized for almost two decades. Because photoexcitation of trans-azobenzene produces the cis-isomer in solution, it has generally been inferred that the macroscopic structural changes occurring in materials are also initiated by a similar large-amplitude trans-to-cis isomerization. This work provides the first demonstration that a trans-to-cis photoisomerization occurs in polycrystalline azobenzene, and is consistent with the previously hypothesized nature of the trigger in the photoactuated mechanisms of the materials in question. It is also demonstrated that under low irradiance, trans-to-cis isomerization occurs in the solid (not via a pre-melted phase); and the presence of the cis-isomer thus lowers the melting point of the sample, providing a liquid phase. A variety of experimental techniques were employed, including X-ray diffraction measurements of polycrystalline azobenzene during exposure to laser irradiation and fluorescence measurements of the solid sample. A practical consequence of this work is that it establishes trans-azobenzene as an easily obtainable and well-defined control for monitoring photoinduced structural changes in X-ray diffraction experiments, using easily accessible laser wavelengths.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Photoinduced Trans‐to‐cis Phase Transition of Polycrystalline Azobenzene at Low Irradiance Occurs in the Solid State

et al. 2017

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“…Figure 1 shows the UV/Vis absorption spectrum of PNA monomer 3, which exhibited a characteristic broad absorption band centered at 414 nm (in dichloromethane) corresponding to π -π * transition of the trans-azo moiety. [12] Upon illumination of 3 with near-UV light from a simple and convenient handheld source (366 nm), a decrease in the intensity of π -π * band at 414 nm (trans) was observed corresponding to the light-driven trans → cis isomerization. Irradiation of the peak maximum was done to minimize potential photochemical degradation of the dye.…”

Section: Resultsmentioning

confidence: 99%

“…Azobenzenes possessing a ring substituted with an electron-donating substituent, such as a dialkylamine, usually show a strong absorbance near 400 nm or slightly longer wavelengths and display similar photophysical behavior. [12] Herein, we report the synthesis of N,N -dimethylaminophenylazobenzene moiety as an integral component of a PNA monomer. This monomer is of interest because of its potential to photoregulate hybridization and as a mimic of the universal quencher DABCYL (4-((4-(dimethylamino)phenyl)azo)benzoic acid) for use in molecular beacons.…”

Section: Introductionmentioning

confidence: 99%

An Azo-Based PNA Monomer: Synthesis and Spectroscopic Study

Moustafa

Hudson

2011

Nucleosides, Nucleotides and Nucleic Acids

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The full synthetic details and photospectroscopic characterization of a peptide nucleic acid (PNA) monomer suitable for Fmoc-based oligomerization chemistry that bears an azobenzene moiety as a base surrogate are reported. The monomer showed the ability to quench the fluorescence emission of fluorescein and pyrene luminophores and proved to be a competent Föster resonance energy transfer partner in a PNA-based molecular beacon.

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“…30 Thus, the majority of the electron injection processes at 400~500 nm excitations occur at least earlier than 5 ps. Thus, we conclude that the electron injection efficiency is not influenced by the difference in the electronic couplings.…”

mentioning

confidence: 99%

Dye-Anchoring Functional Groups on the Performance of Dye-Sensitized Solar Cells: Comparison between Alkoxysilyl and Carboxyl Groups

Matta

Kakiage²,

Makuta

et al. 2014

J. Phys. Chem. C

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We have compared two dye anchoring functional groups, alkoxysilyl and carboxyl groups, to investigate their influence on the performance of dye sensitized solar cells. Dimethylaminoazobenzene was selected as a chromophore possessing a donor-accepter transition for the light absorption. Electrochemical and optical measurements were performed for 4-dimethylaminoazobenzene-4'-carboxylic acid and 4-dimethylaminoazobenzene-4'-triethoxysilane attached TiO 2 films. Electrochemical measurements and DFT calculation indicated almost identical potential energy levels and electron density of HOMO and LUMO states between these two dyes. Solar cell APCE spectra and charge recombination kinetics at the dye/TiO 2 interface revealed almost identical charge transfer rates/yields from and to the dye. The difference was observed on improvement of an open circuit photovoltage (Voc) by 60 mV and on the lifetimes of an electron in the TiO 2 conduction band for the dye with the alkoxysilyl functional group compared to the carboxyl group, suggesting that an alkoxysilyl functional group is more attractive to retard the charge recombination reaction between an electron in the TiO 2 conduction band and an oxidized form of an electrolyte redox couple. The highest solar energy conversion efficiency of 2.6 % was achieved for dye sensitized solar cells based on an azobenzene dye sensitizer under AM1.5G, one sun condition.

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The solvent-dependent isomerization dynamics of 4-(dimethylamino)azobenzene (DMAAB) studied by subpicosecond pump–probe spectroscopy

Cited by 34 publications

References 18 publications

Photoinduced Trans‐to‐cis Phase Transition of Polycrystalline Azobenzene at Low Irradiance Occurs in the Solid State

Photoinduced Trans‐to‐cis Phase Transition of Polycrystalline Azobenzene at Low Irradiance Occurs in the Solid State

An Azo-Based PNA Monomer: Synthesis and Spectroscopic Study

Dye-Anchoring Functional Groups on the Performance of Dye-Sensitized Solar Cells: Comparison between Alkoxysilyl and Carboxyl Groups

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