Effect of the Chloro-Substitution on Electrochemical and Optical Properties of New Carbazole Dyes

Krawczyk, Przemysław; Jędrzejewska, Beata; Seklecka, Klaudia; Cytarska, Joanna; Łączkowski, Krzysztof Z.

doi:10.3390/ma14113091

Cited by 6 publications

(2 citation statements)

References 123 publications

(110 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The theoretical absorption maxima (

) are shown in Table S4 . According to the results obtained earlier [ 55 , 56 , 57 , 58 , 59 ], PBE0 gives the best agreement with the experimental values and should be considered as a reference. Comparing experimental measurements with vertical values, for A-1 the PBE0 functional shifts the position of the maximum

towards longer waves, while for A-2 and A-3 it shifts towards longer waves.…”

Section: Resultsmentioning

confidence: 79%

Can a Small Change in the Heterocyclic Substituent Significantly Impact the Physicochemical and Biological Properties of (Z)-2-(5-Benzylidene-4-oxo-2-thioxothiazolidin-3-yl)acetic Acid Derivatives?

Szlapa-Kula,

Kula,

Kaźmierski

et al. 2024

Sensors

Self Cite

View full text Add to dashboard Cite

Rhodanine-3-acetic acid derivatives are attractive compounds with versatile effects. What is very important is that compounds of this type have many biological properties. They are tested, among others, as fluorescent probes for bioimaging and aldose reductase inhibitors. Rhodanine-3-acetic acid derivatives also have antibacterial, antifungal and anticancer activity. The presented work demonstrates that a slight change in the five-membered heterocyclic substituent significantly affects the properties of the compounds under consideration. Three rhodanine-3-acetic acid derivatives (A-1–A-3) were obtained in the Knoevenagel condensation reaction with good yields, ranging from 54% to 71%. High thermal stability of the tested compounds was also demonstrated above 240 °C. The absorption and emission maxima in polar and non-polar solvents were determined. Then, the possibility of using the considered derivatives for fluorescence bioimaging was checked. Compounds A-1 and A-2 were successfully used as fluorescent dyes of fixed cells of mammalian origin. In addition, biological activity tests against bacteria and fungi were carried out. Our results showed that A-1 and A-2 showed the most excellent antimicrobial activity among the newly synthesized compounds, especially against Gram-positive bacteria.

show abstract

“…The theoretical absorption maxima (

towards longer waves, while for A-2 and A-3 it shifts towards longer waves.…”

Section: Resultsmentioning

confidence: 79%

Can a Small Change in the Heterocyclic Substituent Significantly Impact the Physicochemical and Biological Properties of (Z)-2-(5-Benzylidene-4-oxo-2-thioxothiazolidin-3-yl)acetic Acid Derivatives?

Szlapa-Kula,

Kula,

Kaźmierski

et al. 2024

Sensors

Self Cite

View full text Add to dashboard Cite

show abstract

“…The vertical absorption and emission maxima were estimated based on the time-dependent density functional theory (TDDFT) [39] by including the statespecific (SS) corrected linear response (cLR) approach [40]. Following previous research results [41][42][43][44][45][46], in this case, the PBE0 functional was used as it describes the electrical properties with the smallest error in relation to the experimental values. The dipole moment and polarity of the charge-transfer state (CT, µ CT ) were evaluated by the numerical differentiation of the excitation energies (E) as follows:…”

Section: Computational Detailsmentioning

confidence: 99%

The Influence of the Alkylamino Group on the Solvatochromic Behavior of 5-(4-substituted-arylidene)-1,3-dimethylpyrimidine-2,4,6-triones: Synthesis, Spectroscopic and Computational Studies

Pyszka,

Krawczyk,

Jędrzejewska

2024

Materials

Self Cite

View full text Add to dashboard Cite

Advances in electronics and medical diagnostics have made organic dyes extremely popular as key functional materials. From a practical viewpoint, it is necessary to assess the spectroscopic and physicochemical properties of newly designed dyes. In this context, the condensation of 1,3-dimethylbarbituric acid with electron-rich alkylaminobenzaldehyde derivatives has been described, resulting in a series of merocyanine-type dyes. These dyes exhibit intense blue-light absorption but weak fluorescence. An electron-donating alkylamino group at position C4 is responsible for the solvatochromic behavior of the dyes since the lone electron pair of the nitrogen atom is variably delocalized toward the barbituric ring, which exhibits electron-withdrawing properties. This was elucidated, taking into account the different geometry of the amino group. The intramolecular charge transfer in the molecules is responsible for the relatively high redshift in absorption and fluorescence spectra. Additionally, an increase in solvent polarity moves the absorption and fluorescence to lower energy regions. The observed solvatochromism is discussed in terms of the four-parameter Catalán solvent polarity scale. The differences in the behavior of the dyes were quantified with the aid of time-dependent density functional theory calculations. The obtained results made it possible to find regularities linking the basic spectroscopic properties of the compounds with their chemical structure. This is important in the targeted search for new, practically important dyes.

show abstract

Advancing Optoelectronics with Benzonitriles: Theoretical Understanding, Experimental Realization, and Single‐Molecule White Light Emission

Szukalski,

Szukalska,

El Karout

et al. 2024

Adv Materials Technologies

View full text Add to dashboard Cite

Benzonitrile derivatives (BDs) are very promising for applications in materials science, photonics, and optoelectronics due to their intriguing electronic and optical properties. This study comprehensively investigates BDs, aiming to uncover their fundamental characteristics and potential applications. Using advanced theoretical techniques like Gaussian software, it is gained unprecedented insights into the photoinduced isomerization phenomenon for all‐optical switching in these compounds. The theoretical framework clarifies molecular transition states and explores a range of properties, providing a comprehensive understanding of BDs. Empirical data on the emission properties of BDs, from fluorescence analyses in liquid solutions to light amplification in solid‐state PMMA thin films, complement the theoretical examinations. Notably, white light emission from a single benzonitrile compound is achieved, showcasing its potential for data transmission through Li‐Fi technology. Finally, the all‐optical switching phenomenon in BDs using 3rd order nonlinear optical effects is experimentally validated. This complementary and comprehensive study advances understanding of BDs and demonstrates their potential for practical applications in emerging photonic and optoelectronic technologies.

show abstract

Effect of the Chloro-Substitution on Electrochemical and Optical Properties of New Carbazole Dyes

Cited by 6 publications

References 123 publications

Can a Small Change in the Heterocyclic Substituent Significantly Impact the Physicochemical and Biological Properties of (Z)-2-(5-Benzylidene-4-oxo-2-thioxothiazolidin-3-yl)acetic Acid Derivatives?

Can a Small Change in the Heterocyclic Substituent Significantly Impact the Physicochemical and Biological Properties of (Z)-2-(5-Benzylidene-4-oxo-2-thioxothiazolidin-3-yl)acetic Acid Derivatives?

The Influence of the Alkylamino Group on the Solvatochromic Behavior of 5-(4-substituted-arylidene)-1,3-dimethylpyrimidine-2,4,6-triones: Synthesis, Spectroscopic and Computational Studies

Advancing Optoelectronics with Benzonitriles: Theoretical Understanding, Experimental Realization, and Single‐Molecule White Light Emission

Contact Info

Product

Resources

About