Fluorene vs carbazole substituent at quinoline core toward organic electronics

Słodek, Aneta; Zych, Dawid; Maroń, Anna; Golba, Sylwia; Schab‐Balcerzak, Ewa; Janeczek, Henryk; Siwy, Mariola; Maćkowski, Sebastian

doi:10.1016/j.dyepig.2019.03.032

Cited by 31 publications

(21 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Also, no reduction processes were observed which indicates the irreversible oxidation of the samples. Low onset oxidation potential values are related to low ionization potentials, which reflect the enhanced ability of the diphenylfluorene–biphenyl couple to donate electrons compared to similar small molecules or polymers containing fluorene‐based moieties …”

Section: Resultsmentioning

confidence: 99%

“…Low onset oxidation potential values are related to low ionization potentials, which reflect the enhanced ability of the diphenylfluorene-biphenyl couple to donate electrons compared to similar small molecules or polymers containing fluorene-based moieties. [51][52][53][54] From the voltammograms and the absorption spectra, the values of the highest occupied molecular orbital (HOMO) energies, lowest unoccupied molecular orbital (LUMO) energies and optical bandgap were obtained for each sample ( Table 4). The values of HOMO energy levels were calculated from E HOMO = −(E Ox onset + 4.80 − 0.09 eV), where 0.09 eV corresponds to the E 1/2 potential of the ferrocene/ferrocenium (Fc/Fc + ) redox couple.…”

Section: Cyclic Voltammetrymentioning

confidence: 99%

See 1 more Smart Citation

New cardo silylated poly(azomethine)s containing 9,9′‐diphenylfluorene units as materials with Brønsted acid‐dependent fluorescence

Hauyon

Garrido‐Gatica

Sobarzo

et al. 2019

Polymer International

View full text Add to dashboard Cite

Aromatic poly(azomethine)s have been studied due to their attractive properties such as high thermal stability, semiconducting behavior and the ability to coordinate species with their imine units (CN). In this paper, the synthesis and characterization of two novel silylated poly(azomethine)s containing cardo units are reported. These materials were highly soluble in organic solvents such as chloroform and m‐cresol and were thermally stable, and PAzMC1 exhibited a high glass transition temperature value (287 °C), while that for PAzMC2 was not observed. UV–visible spectrophotometry revealed absorption bands related to the aromatic backbone of both PAzMCs, 300–285 nm in tetrahydrofuran and 310–301 nm in dimethylsulfoxide, and bands attributed to the conjugated imine unit at around 350 nm. In order to investigate the phenomenon of the emission of fluorescence promoted by dopant agents with regard to potential optoelectronic applications, the materials were doped with H2SO4 and their optical and electrochemical properties investigated. Thus, the absorption band of the imine group was suppressed due to the nitrogen atoms being protonated. Fluorescence spectroscopy analysis developed in dilute solutions of polymers showed no emission from the undoped polymers, whereas the acid‐doped species emitted fluorescence in the UV and violet regions (322 nm). Cyclic voltammetry measurements were carried out and HOMO–LUMO energies were estimated. This study provides a starting point for the development of new poly(azomethine)s with doping‐dependent emission. © 2019 Society of Chemical Industry

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Cyclic Voltammetrymentioning

confidence: 99%

New cardo silylated poly(azomethine)s containing 9,9′‐diphenylfluorene units as materials with Brønsted acid‐dependent fluorescence

Hauyon

Garrido‐Gatica

Sobarzo

et al. 2019

Polymer International

View full text Add to dashboard Cite

show abstract

“…Some materials can be successfully used to produce both solar cells [117] and OLEDs [118]. Chemical compounds of pyrazoloquinoline derivatives have also been successfully used in OLED emission layers [119,120].…”

Section: Other Applicationsmentioning

confidence: 99%

Application of quinoline derivatives in third-generation photovoltaics

Lewińska

Sanetra

Marszałek

2021

J Mater Sci: Mater Electron

View full text Add to dashboard Cite

Among many chemical compounds synthesized for third-generation photovoltaic applications, quinoline derivatives have recently gained popularity. This work reviews the latest developments in the quinoline derivatives (metal complexes) for applications in the photovoltaic cells. Their properties for photovoltaic applications are detailed: absorption spectra, energy levels, and other achievements presented by the authors. We have also outlined various methods for testing the compounds for application. Finally, we present the implementation of quinoline derivatives in photovoltaic cells. Their architecture and design are described, and also, the performance for polymer solar cells and dye-synthesized solar cells was highlighted. We have described their performance and characteristics. We have also pointed out other, non-photovoltaic applications for quinoline derivatives. It has been demonstrated and described that quinoline derivatives are good materials for the emission layer of organic light-emitting diodes (OLEDs) and are also used in transistors. The compounds are also being considered as materials for biomedical applications.

show abstract

“… 3 , 4 For example, 9,9-dialkylated fluorene derivatives ( Figure 1 , I ) have been used extensively as efficient π-spacers in the construction of photoluminescent materials, dyes for dye-sensitized solar cells, and other optoelectronic applications. 5 − 11 The dialkylation significantly enhances solubility and has an influence on molecular packing, e.g., π-stacking; however, it does not significantly alter the optical and electronic properties compared to the parent 2H-fluorene. 12 Similarly, dibenzoheteroles of group 14 to 16 have found widespread use as optoelectronic materials.…”

Section: Introductionmentioning

confidence: 99%

Golden Age of Fluorenylidene Phosphaalkenes–Synthesis, Structures, and Optical Properties of Heteroaromatic Derivatives and Their Gold Complexes

et al. 2020

View full text Add to dashboard Cite

The substitution of 2,7-dibromo-9-fluorenyl phosphaalkenes with heteroaromatic substituents (bithiophene, benzothiophene, pyridine) offers access to interesting push–pull dye molecules. Steric shielding due to the bulky P-substituent gives marked different reactivities at the 2- and 7-positions, allowing the synthesis of mixed/asymmetric derivatives. Further functionalization via gold(I) coordination was demonstrated and increased the acceptor character, concomitant with a red-shifted absorption.

show abstract

Fluorene vs carbazole substituent at quinoline core toward organic electronics

Cited by 31 publications

References 33 publications

New cardo silylated poly(azomethine)s containing 9,9′‐diphenylfluorene units as materials with Brønsted acid‐dependent fluorescence

New cardo silylated poly(azomethine)s containing 9,9′‐diphenylfluorene units as materials with Brønsted acid‐dependent fluorescence

Application of quinoline derivatives in third-generation photovoltaics

Golden Age of Fluorenylidene Phosphaalkenes–Synthesis, Structures, and Optical Properties of Heteroaromatic Derivatives and Their Gold Complexes

Contact Info

Product

Resources

About