Self-assembling behaviour of new functional photosensitive cinnamoyl-based reactive mesogens

Bubnov, Alexej; Cigl, Martin; Sedláčková, Nela; Pociecha, Damian; Böhmová, Zuzana; Hamplová, Věra

doi:10.1080/02678292.2020.1783586

Cited by 21 publications

(6 citation statements)

References 92 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Cinnamate-composed LC materials were mostly approved to be important in applications and exhibited nematogenic phases [47][48][49][50][51][52][53][54][55][56][57]. In addition, the optical behavior of nematogenic materials was shown to be strongly enhanced by the inclusion of a lateral fluorine (F) atom.…”

Section: Introductionmentioning

confidence: 99%

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: 99%

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

“…While increasing the cooling rate, the Iso-N and N-SmA phase transition temperatures slightly decreased, and the stability of the phases increased, upon heating, the situation was the opposite (see Figure 6 ). However, the transition to the solid crystal (Cr) phase shows a clear sign of super-cooling [ 34 , 51 ], being more pronounced especially at cooling rates higher than 40 K. This effect is also related to the monotropic character of the lower temperature range of the SmA phase.…”

Section: Resultsmentioning

confidence: 99%

“…Utilisation of the various types of polymeric backbones (polyacrylate [ 16 ], polymethacrylate [ 4 , 21 , 22 , 24 ], polysiloxane [ 23 , 25 , 26 , 27 , 28 ], polyurethane [ 29 ], etc.) for the design of LC macromolecular materials requires a specific molecular structure of the reactive terminal groups (acrylate [ 16 , 30 , 31 , 32 , 33 ], methacrylate [ 4 , 21 , 22 , 32 ], vinyl [ 12 , 23 , 27 , 34 ], thiols [ 35 , 36 , 37 ], etc.) of the respective monomeric LC materials used as functional reactive mesogens.…”

Section: Introductionmentioning

confidence: 99%

Design and Self-Assembling Behaviour of Calamitic Reactive Mesogens with Lateral Methyl and Methoxy Substituents and Vinyl Terminal Group

Bubnov

Cigl

Penkov³

et al. 2021

Polymers

Self Cite

View full text Add to dashboard Cite

Smart self-organising systems attract considerable attention in the scientific community. In order to control and stabilise the liquid crystalline behaviour, and hence the self-organisation, the polymerisation process can be effectively used. Mesogenic units incorporated into the backbones as functional side chains of weakly cross-linked macromolecules can become orientationally ordered. Several new calamitic reactive mesogens possessing the vinyl terminal group with varying flexible chain lengths and with/without lateral substitution by the methyl (methoxy) groups have been designed and studied. Depending on the molecular structure, namely, the type and position of the lateral substituents, the resulting materials form the nematic, the orthogonal SmA and the tilted SmC phases in a reasonably broad temperature range, and the structure of the mesophases was confirmed by X-ray diffraction experiments. The main objective of this work is to contribute to better understanding of the molecular structure–mesomorphic property relationship for new functional reactive mesogens, aiming at further design of smart self-assembling macromolecular materials for novel sensor systems.

show abstract

“…A wide variety of photochromic materials exists undergoing valence isomerisations, E/Z isomerisations, cycloadditions or tautomerisations, among others. The photochromic processes can involve pericyclic reactions (spiropyrans/-oxazine, diarylethenes), E/Z isomerisations (azobenzenes, dithienylethene, stilbenes), photo-induced bond cleavages (triarylmethanes, perchlorotoulenes), intramolecular hydrogen-bond transfer (anils and polycyclic quinones) and electron transfer (viologens) [1][2][3][4][5]. Among these, azobenzene has been widely investigated as a photochromic group in lightresponsive materials due to its rapid, reversible and high quantum yield photo-isomerisation between E and Z conformations [6][7][8][9].…”

Section: Introductionmentioning

confidence: 99%

A new light-responsive resistive random-access memory device containing hydrogen-bonded complexes

Velayutham

Azmina

Manickam-Achari

et al. 2021

Journal of Photochemistry and Photobiology A: Chemistry

View full text Add to dashboard Cite

In the search to obtain new and more efficient components of memory devices, we report the photochromic, dielectric and electrochemical response of a light-responsive organic compound, and its memory performance under electrical fields. The so-called N(1)-[12-(4-(4'-isobutyloxyphenyldiazo)phenoxy)dodecyloxy)]thymine, tAZOi, molecule contains one azobenzene group, which provides with photochromic character, and one terminal thymine group, capable to form hydrogen bonds and assemble supramolecular dimers, (tAZOi)2. We have calculated the optical absorption coefficient, extinction coefficient and refractive index of tAZOi, which obeys the single oscillator Wemple-DiDomenico model. An ITO/tAZOi/Al device has been prepared and presents two switchable conductance states with preservation of memory performance. The mechanism linked to the resistive randomaccess memory (RRAM) has been evaluated by molecular modelling and is controlled by ptype conduction, possibly involving hydrogen-bonding. Upon UV irradiation at ~365 nm, tAZOi displays an increase in the complex permittivity driven by trans-to-cis

show abstract

Self-assembling behaviour of new functional photosensitive cinnamoyl-based reactive mesogens

Cited by 21 publications

References 92 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

Design and Self-Assembling Behaviour of Calamitic Reactive Mesogens with Lateral Methyl and Methoxy Substituents and Vinyl Terminal Group

A new light-responsive resistive random-access memory device containing hydrogen-bonded complexes

Contact Info

Product

Resources

About