Synthesis, spectroscopic and TD-DFT quantum mechanical study of azo-azomethine dyes. A laser induced trans-cis-trans photoisomerization cycle

Georgiev, Anton; Kostadinov, Anton; Ivanov, Deyan; Dimov, D; Stoyanov, Simeon; Nedelchev, Lian; Nazarova, Dimana; Yancheva, Denitsa

doi:10.1016/j.saa.2017.11.016

Cited by 28 publications

(10 citation statements)

References 33 publications

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“…36,37 Special attention has been focused on quinazoline-based compounds, [38][39][40] which belong to the class of nitrogen-containing heterocyclic compounds. The photochemical process in quinazolinones proceeds at the -N-N]C(H) array (in contrast to the N]N bond analysed in azobenzene 41,42 and its derivatives 43,44 ), which is part of a large p-system including a lone electron pair in the sp 2 -hybridised orbital of the nitrogen atom of the azomethine group. As shown previously, 45,46 photoisomerisation specically proceeds around the N-N linkage in the -N-N]C(H) atom array in quinazolinones.…”

Section: Introductionmentioning

confidence: 99%

A study of the photochemical behaviour and relaxation mechanisms of anti–syn isomerisation around quinazolinone –N–N bonds

2022

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Section: Introductionmentioning

confidence: 99%

A study of the photochemical behaviour and relaxation mechanisms of anti–syn isomerisation around quinazolinone –N–N bonds

2022

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“…The green surface is spread over the entire molecule of C-466 suggests that entire molecule is active in solvent. The robust interactions site of sample is found to be at ester group with the surrounding media [41,42].…”

Section: Solvent Accessible Surfacesmentioning

confidence: 97%

Solvent Dependence on Structure and Electronic Properties of 7-(Diethylamino) - 2H -1- Benzopyran-2- one (C-466) Laser Dye

Renuka

Nadaf²,

Sriprakash³

et al. 2018

J Fluoresc

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In this work, we studied influences on the absorption and fluorescence emission spectra of coumarin-4066 (C-466) with different solvent polarity scale. The spectral shifts reflect the effect of the equilibrium solvents association across the energized solute particle, which adjusts inertially as a result of quick charge realignment upon radiative deactivation to the lowest electronic state. The dipole moments of C-466 are determined by employing the Bakhshiev, Kawski-Chamma-Viallet, Lippert-Mataga and McRae relations. The results from all these methods are, excited state dipole moment of C-466 is higher than the ground state dipole moments and which indicates molecule is less polar in the ground state. Theoretical analysis was also carried out by Density Functional theory (DFT and TD -DFT) employing the BECKE-1998 (exchange)/STO-6G basic set in ethanol solvent and in vacuum medium. The HOMO-LUMO, Solvent Accessible Surfaces (SAS) and Molecular Electrostatic Potential (MEP) were analysed to acquire additional knowledge of the molecular arrangement and electronic properties of C-466. These photophysical properties suggest delineation can be mauled for laying out new luminescent tests for various solvents microenvironment.

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“…The arguments for the development of the azobenzene photoisomerization process by inversion or rotation are the subject of numerous molecular simulation studies [ 25 , 26 , 27 , 28 ]. A large number of articles track the computational characterization of these photocontrolled materials due to their prospective applications in different fields such as liquid crystals [ 29 , 30 , 31 ], optical data storage [ 32 ], photosensitive micelles [ 33 ], triggers in protein folding [ 34 ], and so on. Due to the complexity of the molecular migration phenomenon that induces the SRG formation process, the number of molecular studies is significantly lower [ 35 , 36 , 37 ].…”

Section: Introductionmentioning

confidence: 99%

Evaluation of Local Mechanical and Chemical Properties via AFM as a Tool for Understanding the Formation Mechanism of Pulsed UV Laser-Nanoinduced Patterns on Azo-Naphthalene-Based Polyimide Films

Stoica¹,

Epure

Constantin³

et al. 2021

Nanomaterials

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Aromatic polyimides containing side azo-naphthalene groups have been investigated regarding their capacity of generating surface relief gratings (SRGs) under pulsed UV laser irradiation through phase masks, using different fluencies and pulse numbers. The process of the material photo-fluidization and the supramolecular re-organization of the surface were investigated using atomic force microscopy (AFM). At first, an AFM nanoscale topographical analysis of the induced SRGs was performed in terms of morphology and tridimensional amplitude, spatial, hybrid, and functional parameters. Afterward, a nanomechanical characterization of SRGs using an advanced method, namely, AFM PinPoint mode, was performed, where the quantitative nanomechanical properties (i.e., modulus, adhesion, deformation) of the nanostructured azo-polyimide surfaces were acquired with a highly correlated topographic registration. This method proved to be very effective in understanding the formation mechanism of the surface modulations during pulsed UV laser irradiation. Additionally to AFM investigations, confocal Raman measurements and molecular simulations were performed to provide information about structured azo-polyimide chemical composition and macromolecular conformation induced by laser irradiation.

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Synthesis, spectroscopic and TD-DFT quantum mechanical study of azo-azomethine dyes. A laser induced trans-cis-trans photoisomerization cycle

Cited by 28 publications

References 33 publications

A study of the photochemical behaviour and relaxation mechanisms of anti–syn isomerisation around quinazolinone –N–N bonds

A study of the photochemical behaviour and relaxation mechanisms of anti–syn isomerisation around quinazolinone –N–N bonds

Solvent Dependence on Structure and Electronic Properties of 7-(Diethylamino) - 2H -1- Benzopyran-2- one (C-466) Laser Dye

Evaluation of Local Mechanical and Chemical Properties via AFM as a Tool for Understanding the Formation Mechanism of Pulsed UV Laser-Nanoinduced Patterns on Azo-Naphthalene-Based Polyimide Films

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