Triphenylamine-based allylidenemalononitrile chromophores: synthesis, and photophysical and second-order nonlinear optical properties

Çatal, Emine; Keleş, Ergin; Seferoğlu, Nurgül; Achelle, Sylvain; Barsella, Alberto; Guen, Françoise Robin Le; Seferoğlu, Zeynel

doi:10.1039/c8nj02794c

Cited by 22 publications

(9 citation statements)

References 57 publications

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“…For instance, in DCM, dye 8 showed absorption and emission maxima at 546 and 636 nm, whereas the maxima of dye 3 were observed at 531 and 617 nm, respectively. Moreover, both the styryl and the Schiff bases showed greater red shifts compared to the previously reported counterparts [31,32]. As can be seen from Figure 4, the absorption maxima of dyes 3-6 and 8-11 depended on the electron-donating nature of the substituents, and the values of the maximum absorption wavelengths in-creased in the following order: 4-morpholinyl (6, 11) < 4-piperidinyl (5, 10) < 4-pyrolidinyl (4, 9) < 4-julolidinyl (3,8).…”

Section: Substituent Effectsmentioning

confidence: 59%

“…The protocol for the synthesis of dye 2 was published previously [31,32]. Dyes 3-7 were synthesized using 2 and the appropriate benzaldehyde.…”

Section: Methodsmentioning

confidence: 99%

“…As depicted in Scheme 1, dye 2 was obtained in good yield by reacting malononitrile and 4-aminoacetophenone (compound 1) according to our previous published procedure [31,32].…”

Section: Synthesismentioning

confidence: 99%

“…The charge delocalization upon excitation leads to a red-shifted emission which is viable for the detection of various substrates in biological tissues and samples [28][29][30]. Recently, there was an increasingly growing interest in studies regarding push-pull organic molecules comprising of the dicyanomethylene group as a strong electron-accepting group coupled with various donors connected via a π-conjugation bridge [31][32][33]. Such dyes offer good NLO characteristics when compared to Disperse Red 1 as well as remarkable thermal stabilities with dissociation temperatures up to 300 °C [31,32].…”

Section: Introductionmentioning

confidence: 99%

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Styryl-based new organic chromophores bearing free amino and azomethine groups: synthesis, photophysical, NLO, and thermal properties

Putra¹,

Çakmaz²,

Seferoğlu³

et al. 2020

Beilstein J. Org. Chem.

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Herein we report the synthesis and characterization of a new series of styryl-based push-pull dyes containing a free amino group and their Schiff base derivatives. The dyes include the dicyanomethylene group as an acceptor and different para-substituted alkylamines as donors. Morever as a proton-sensitive group a pyridin-2-yl substituent was attached to the para-position of the phenyl moiety in both series of compounds. The photophysical properties of the dyes were examined in various solvents with different polarities and showed absorption in the visible region and green-red emission with low quantum yields. The absorption and the emission maxima were shifted bathocromically by increasing the solvent’s polarity. However, there was no correlation with the polarity parameters of the solvents. The pH-sensitive properties of all prepared Schiff bases were examined against TBAOH in DMSO, via deprotonation of the OH group in the salicylidene moiety and their reverse protonation was also investigated using TFA. The Schiff bases exhibited a bathochromic shift upon the addition of TBAOH to their solutions in DMSO. Therefore, they showed potential to be utilized as colorimetric and luminescence pH sensors. The second-order nonlinear optical (NLO) responses of the dyes were measured by the electric field-induced second harmonic (EFISH) generation method. The highest μβ values were obtained for the dyes bearing the julolidine donor as 1430 × 10−48 esu (for free amino derivative) and 1950 × 10−48 esu (for Schiff base derivative), respectively. The structural and electronic properties of the dyes as well as their NLO properties were further studied using DFT calculations. The thermal stabilities of all dyes were evaluated by thermogravimetric analysis (TGA). The TGA data showed that all dyes were thermally stable up to 250 °C.

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Section: Substituent Effectsmentioning

confidence: 59%

“…The protocol for the synthesis of dye 2 was published previously [31,32]. Dyes 3-7 were synthesized using 2 and the appropriate benzaldehyde.…”

Section: Methodsmentioning

confidence: 99%

“…As depicted in Scheme 1, dye 2 was obtained in good yield by reacting malononitrile and 4-aminoacetophenone (compound 1) according to our previous published procedure [31,32].…”

Section: Synthesismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Styryl-based new organic chromophores bearing free amino and azomethine groups: synthesis, photophysical, NLO, and thermal properties

Putra¹,

Çakmaz²,

Seferoğlu³

et al. 2020

Beilstein J. Org. Chem.

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“…Hence, NLOphoric materials with the azo unit in skeleton have useful applications in printing systems, information storage devices, second harmonic generations, dyes sensitized solar cells (DSSCs), sensing devices and optical switches, information technology applications, photo recording devices, detection of radiations and optical data storage . D‐π‐A motifs find application as NLOphores . Azo dyes with efficient donor and acceptor functions like thiophene, vinyl, and thiazole bridges possess large molecular hyperpolarizabilities originating from strong intramolecular charge transfer (ICT) and low optical damages .…”

Section: Introductionmentioning

confidence: 99%

NLO Properties of 2‐Napthol Monoazo Disperse Dyes by DFT and Z‐Scan Technique – A Detailed Study

Yadav

Sreenath²,

Chitrambalam³

et al. 2019

ChemistrySelect

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The non‐linear and linear optical properties of 2‐napthol based four monoazo dyes were examined by computational and Z‐scan methods. Time‐dependent (TD)‐density functional theory (DFT) computations were used to evaluate the linear polarizability (α), first‐order hyperpolarizability (β) and second‐order hyperpolarizability (γ) using global hybrid and range separated hybrid functionals at 6–311+ G (d) basis set. The functional, ωB97 performed better in the determination of linear polarizability (α) and ωB97X−D performed better in the determination of the first‐order hyperpolarizability (β) and second‐order hyperpolarizability (γ) among the global hybrid and range separated hybrid functionals. To support our theoretical findings for α, β, and γ, we have correlated with the Hammett‐coefficient (σ), excited state coefficient (σex) as well as by hyper‐hardness (Γ) relations. Third order NLO parameters – non‐linear refractive index (η2), non‐linear absorption coefficient (β), real parts and the imaginary parts of third order susceptibility (χ(3)), and second order hyperpolarizability (γ) were investigated by close and open aperture methods using Z‐scan technique. The –NO2 substituted dye 2 shows higher value of molecular susceptibility (χ(3)), polarizability (α), and hyperpolarizability (β, γ) parameters among the studied azo dyes. They are likely to have potential applications in optoelectronics and photonics.

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Electron‐Withdrawing Substituted Quinazoline Push‐Pull Chromophores: Synthesis, Electrochemical, Photophysical and Second‐Order Nonlinear Optical Properties

et al. 2020

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A series of chromophores bearing 4‐cyanoquinazoline, 2‐(4‐cyanophenyl)quinazoline or 2‐(4‐trifluorophenyl)quinazoline electron–acceptor (A) and 5‐(4‐aminophenyl)thiophen‐2‐yl or 4‐aminophenyl electron‐donor (D) units has been designed. The influence of the electron‐withdrawing substituent on the pyrimidine core as well as the nature of the amino electron donating group has been studied by cyclic voltammetry, UV/Vis and emission spectroscopy. Whereas 2‐(4‐cyanophenyl)quinazoline and 2‐(4‐trifluorophenyl)quinazoline derivatives are highly luminescent in chloroform solution, 4‐cyanoquinazolines are poorly emissive. Interestingly all compounds are luminescent in the solid state with the emission ranging from blue to red. The second order nonlinear optical properties were studied using electric field induced second harmonic generation (EFISH) method. Quantum‐chemical calculations corroborate the aforementioned experimental results.

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Triphenylamine-based allylidenemalononitrile chromophores: synthesis, and photophysical and second-order nonlinear optical properties

Abstract: A series of NLO chromophores based on a mono-, di- or tri-substituted triphenylamine core and allylidenemalononitrile fragments has been designed.

Cited by 22 publications

References 57 publications

Styryl-based new organic chromophores bearing free amino and azomethine groups: synthesis, photophysical, NLO, and thermal properties

Styryl-based new organic chromophores bearing free amino and azomethine groups: synthesis, photophysical, NLO, and thermal properties

NLO Properties of 2‐Napthol Monoazo Disperse Dyes by DFT and Z‐Scan Technique – A Detailed Study

Electron‐Withdrawing Substituted Quinazoline Push‐Pull Chromophores: Synthesis, Electrochemical, Photophysical and Second‐Order Nonlinear Optical Properties

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