Asymmetric azomethine amines with azobenzene moieties – liquid crystalline and optical properties

Iftime, Manuela-Maria; Cozan, Vasile; Airinei, Anton; Varganici, Cristian–Dragos; Ailiesei, Gabriela-Liliana; Ţîmpu, Daniel; Sava, Ion

doi:10.1080/02678292.2019.1640903

Cited by 18 publications

(5 citation statements)

References 56 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Moreover, they can generate photoactive LC materials because they can easily undergo trans/cis photo-induced isomerization. Thus, azobenzenes are also widely reported [13][14][15][16][17][18][19][20][21][22][23][24][25][26].…”

Section: Introductionmentioning

confidence: 98%

Synthesis, Optical and DFT Characterizations of Laterally Fluorinated Phenyl Cinnamate Liquid Crystal Non-Symmetric System

et al. 2021

View full text Add to dashboard Cite

A new laterally fluorinated unsymmetric liquid crystalline homologous series, based on cinnamate linkage, named 2-fluoro-4-(4-(alkoxy)phenyl)diazenyl)phenyl cinnamate (In), was synthesized and evaluated via different experimental and computational tools. The series had different terminal alkoxy-chain lengths with a lateral F atom in the meta position with respect to the azo moiety. The experimental mesomorphic and optical investigations were carried out using differential scanning calorimetry (DSC) and polarized optical microscopy (POM). Theoretical calculations and geometrical parameter predictions were conducted using the DFT program method at B3LYP/6-311G** level of theory. The results revealed that all the designed compounds exhibited the nematic (N) mesophase enantiotropically. The nematic stability and temperature range were impacted by the terminal alkoxy chain length. Compounds with the shortest chains (I6 and I8) showed a monotropic smectic A (SmA) phase, while the longest chain derivative, I16, possessed enantiotropic Sm A phase. Theoretical density functional theory (DFT) predictions were correlated with the practically observed data from the mesomorphic investigations. Data revealed that the terminal alkoxy and lateral F groups had an essential impact on the total energy of possible geometrical structures and their physical and thermal parameters.

show abstract

Section: Introductionmentioning

confidence: 98%

Synthesis, Optical and DFT Characterizations of Laterally Fluorinated Phenyl Cinnamate Liquid Crystal Non-Symmetric System

et al. 2021

View full text Add to dashboard Cite

show abstract

“…The structure of all the tested compounds were sketched using HyperChem. 20 The geometry and energy of the structures were being optimized using ORCA soware 21 at DFT, B3LYP/cc-pvdz level of theory. The chain A of structure of c-Kit PDB ID 1T46 was selected for docking, 22 cognate ligand and all crystallographic water molecules removed from the macromolecular structure using the LePro module (http:// lephar.com).…”

Section: Molecular Docking Studiesmentioning

confidence: 99%

Green synthesis, anti-proliferative evaluation, docking, and MD simulations studies of novel 2-piperazinyl quinoxaline derivatives using hercynite sulfaguanidine-SA as a highly efficient and reusable nanocatalyst

Esam,

Akhavan,

Mirshafa

et al. 2023

RSC Adv.

View full text Add to dashboard Cite

show abstract

“…Considering the biological relevance and importance of stilbenes in material science, many related synthetic structures can be found in the literature, known as pseudo-stilbenes. These structures have 4 and 4 ′ positions of the two azo rings with electron-donating and electron-withdrawing groups at opposite ends of the aromatic system [33], which include azomethines (-CH=N-) [34][35][36][37], azobenzenes (-N=N-) [20,[38][39][40][41][42], and azo-coupling (-N=N-X-Y-) [26,37,[43][44][45]. Such structures are a well-known class of materials with reported NLO responses due to their potential for applications in photonic devices [46].…”

Section: Introductionmentioning

confidence: 99%

Pseudo-Stilbene- and Azobenzene-Type Systems for Optical Frequency Conversion: Estimating the First-Order Molecular Hyperpolarizability

Araújo,

Rodrigues,

Alencar

et al. 2024

Photonics

View full text Add to dashboard Cite

This study investigates the potential of a set of pseudo-stilbene and azobenzene molecular structures to become optical frequency converters for optical communications based on a detailed exploration of the first-order molecular hyperpolarizability (βHRS), which is the microscopic counterpart of second harmonic generation (SHG). βHRS values were obtained via quantum chemical calculations using the Gaussian 16 software package in solvent and gas-phase media at different wavelengths, i.e., 1064 nm, 1310 nm, and 1510 nm. The latter two wavelengths are of particular interest for optical communications. Our study focused on discerning how the molecular structure influences the βHRS response, explicitly highlighting the influence of the azomethine group (CH=N). The results revealed that the molecular planarity, affected by this group, plays a crucial role in modulating the optical properties. The highest βHRS value in a solvent medium using the CAM-B3LYP/6-311+G(2d,p) level of theory achieved in this work was around 1400 ×10−30cm4startvolt−1, four orders of magnitude higher than KDP (0.2 ×10−30cm4startvolt−1), which is a reference in SHG experiments at 1064 nm. The highest calculated βHRS value at the same level of theory and solvent at 1310 nm and 1550 nm was 631 × 10−30cm4startvolt−1 and 456 × 10−30cm4startvolt−1, respectively. All these values belong to molecular structures with azo-coupling with donor (4-NMe2) and acceptor (4′-NO2) peripheral groups, designated as AB-3.

show abstract

Asymmetric azomethine amines with azobenzene moieties – liquid crystalline and optical properties

Abstract: Supporting Information NMR spectra1D and 2D NMR spectra were recorded on a Bruker Avance III spectrometer, operating at 400.1, 100.6 and 40.6 MHz for 1 H, 13 C and 15 N nuclei, respectively. Samples were recorded with either

Cited by 18 publications

References 56 publications

Synthesis, Optical and DFT Characterizations of Laterally Fluorinated Phenyl Cinnamate Liquid Crystal Non-Symmetric System

Synthesis, Optical and DFT Characterizations of Laterally Fluorinated Phenyl Cinnamate Liquid Crystal Non-Symmetric System

Green synthesis, anti-proliferative evaluation, docking, and MD simulations studies of novel 2-piperazinyl quinoxaline derivatives using hercynite sulfaguanidine-SA as a highly efficient and reusable nanocatalyst

Pseudo-Stilbene- and Azobenzene-Type Systems for Optical Frequency Conversion: Estimating the First-Order Molecular Hyperpolarizability

Contact Info

Product

Resources

About