Optical and photovoltaic properties of salicylaldimine-based azo ligands

Dinçalp, Haluk; Yavuz, Sinem; Haklı, Özgül; Zafer, Ceylan; Ozsoy, Cihan; Durucasu, İnci; İçli, Sıddık

doi:10.1016/j.jphotochem.2009.12.012

Cited by 45 publications

(18 citation statements)

References 38 publications

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“…4,5 These dyes can be used as sensitizers in dye-sensitized solar cells (DSSCs) based on photosensitization of nanocrystalline titanium dioxide, 6 in optical data storage, 7 and in the photorefractive polymer industries. 1,8 These dyes can be classified into three main groups based on their photochemical behavior, 9 where unsubstituted azobenzenes, known as ''azobenzenes'', present relatively poor pp* and np* overlap. The ''aminoazobenzenes'' constitute the second group, which includes azobenzenes with an electrondonor group substituent, characterized by overlapping pp* and np* bands.…”

Section: Introductionmentioning

confidence: 99%

Evidence for excited state intramolecular charge transfer in benzazole-based pseudo-stilbenes

Santos

Descalzo

Gonçalves

et al. 2012

Phys. Chem. Chem. Phys.

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Two azo compounds were obtained through the diazotization reaction of aminobenzazole derivatives and N,N-dimethylaniline using clay montmorillonite KSF as catalyst. The synthesized dyes were characterized using elemental analysis, Fourier transform infrared spectroscopy, and (13)C and (1)H NMR spectroscopy in solution. Their photophysical behavior was studied using UV-vis and steady-state fluorescence in solution. These dyes present intense absorption in the blue region. The spectral features of the azo compounds can be related to the pseudo-stilbene type as well as the E isomer of the dyes. Excitation at the absorption maxima does not produce emissive species in the excited state. However, excitation around 350 nm allowed dual emission of fluorescence, from both a locally excited (LE, short wavelength) and an intramolecular charge transfer (ICT, long wavelength) state, which was corroborated by a linear relation of the fluorescence maximum (ν(max)) versus the solvent polarity function (Δf) from the Lippert-Mataga correlation. Evidence of TICT in these dyes was discussed from the viscosity dependence of the fluorescence intensity in the ICT emission band. Theoretical calculations were also performed in order to study the geometry and charge distribution of the dyes in their ground and excited electronic states. Using DFT methods at the theoretical levels BLYP/Aug-cc-pVDZ, for geometry optimizations and frequency calculations, and B3LYP/6-311+G(2d), for single-point energy evaluations, the calculations revealed that the least energetic and most intense photon absorption leads to a very polar excited state that relaxes non-radioactively, which can be associated with photochemical isomerization.

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Section: Introductionmentioning

confidence: 99%

Evidence for excited state intramolecular charge transfer in benzazole-based pseudo-stilbenes

Santos

Descalzo

Gonçalves

et al. 2012

Phys. Chem. Chem. Phys.

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“…Reactive dyes are the main colorants for cotton fabric dyeing owing to their excellent colour performance , and they attach themselves to the cotton fabric via their reactive groups during the dyeing process. This inspired an attempt to attach reactive dyes to SiO 2 via covalent bonds.…”

Section: Introductionmentioning

confidence: 99%

Mechanism and properties of coloured nanoscale SiO₂ prepared from silica and reactive dyes

Zhang

Tian

et al. 2016

Coloration Technology

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KH560‐modified SiO2 was prepared using tetraethyl orthosilicate (TEOS) and γ‐(2,3‐epoxypropoxy) propytrimethoxysilane (KH560) by the sol–gel method and then coloured with CI Reactive Blue 4 (X‐BR) to prepare coloured nanoscale SiO2. The antisolvent performance and the results of cross‐polarisation/magic angle spinning 13C nuclear magnetic resonance and Fourier transform infrared spectroscopy showed that the reaction of X‐BR with KH560‐modified SiO2 is a two‐step process: X‐BR is firstly adsorbed by KH560‐modified SiO2 via van der Waals forces, and then nucleophilic substitution occurs between dichloro triazine and the epoxy group. The grafting ratio of X‐BR on KH560‐modified SiO2 reached 95% under optimum conditions, i.e. a mass ratio of KH560 to TEOS of 20%, a temperature of 40 °C, a pH of 8.5, and a reaction time of 5 h. X‐ray diffraction analysis and transmission electron microscopy showed that the coloured nanoscale SiO2 was amorphous, with a mean diameter of 216 nm. Experimental application showed that the coloured nanoscale SiO2 had excellent stability to solvents and alkaline solution, and the absorptive capacity of the coloured nanoscale SiO2 in the 200–400 nm region was higher than that of X‐BR. The light fastness of the coloured nanoscale SiO2 reached 5–6 grade.

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“…However, small molecule azomethines are rather seldom tested as materials for OPVs. To the best of our knowledge, only a few papers report photovoltaic properties of AZs [23][24][25], one of which is our work [21]. Based on our former investigations it can be concluded that compounds comprised of imine and imide structure can be considered as perspective materials for organic optoelectronic devices [22,26].…”

Section: Introductionmentioning

confidence: 99%

Azomethine naphthalene diimides as component of active layers in bulk heterojunction solar cells

et al. 2015

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Optical and photovoltaic properties of salicylaldimine-based azo ligands

Cited by 45 publications

References 38 publications

Evidence for excited state intramolecular charge transfer in benzazole-based pseudo-stilbenes

Evidence for excited state intramolecular charge transfer in benzazole-based pseudo-stilbenes

Mechanism and properties of coloured nanoscale SiO₂ prepared from silica and reactive dyes

Azomethine naphthalene diimides as component of active layers in bulk heterojunction solar cells

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Optical and photovoltaic properties of salicylaldimine-based azo ligands

Cited by 45 publications

References 38 publications

Evidence for excited state intramolecular charge transfer in benzazole-based pseudo-stilbenes

Evidence for excited state intramolecular charge transfer in benzazole-based pseudo-stilbenes

Mechanism and properties of coloured nanoscale SiO2 prepared from silica and reactive dyes

Azomethine naphthalene diimides as component of active layers in bulk heterojunction solar cells

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Product

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Mechanism and properties of coloured nanoscale SiO₂ prepared from silica and reactive dyes