Carbazole-based D-π-A molecules: Determining the photophysical properties and comparing ICT effects of π-spacer and acceptor groups

Altınölçek, Nuray; Battal, Ahmet; Vardalli, Cemre Nur; Tavaslı, Mustafa; Yu, Holly A.; Peveler, William J.; Skabara, Peter J.

doi:10.1016/j.molstruc.2021.130494

Cited by 14 publications

(11 citation statements)

References 75 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It is observed that the surge of f w abates the fluorescence emission due to the intensifyication of twisted intramolecular charge transfer (TICT), which exhausts the excited energy. This is also a typical aptitude of ICT compounds. , …”

Section: Resultsmentioning

confidence: 88%

“…This is also a typical aptitude of ICT compounds. 40,41 Besides imparting long-emission wavelengths for QTBT, QTM, and QTE via the ICT establishment, the C�C constructed by Knoevenagel condensation and the thioether moiety are also response sites designed for HSO 3 − and HClO. In succession, fluorescence spectral analysis has been implemented for molecular screening.…”

Section: Photophysical Properties and Molecular Screeningmentioning

confidence: 99%

See 1 more Smart Citation

Taming Janus-Faced Quinoline-Derived Fluorescent Probes for Dual-Channel Distinguishable Visualization of HSO₃^– and HClO in Dried Foods and Living Cells

Xu,

Wang,

Xiao

et al. 2024

J. Agric. Food Chem.

View full text Add to dashboard Cite

With the booming development of food manufacturing, developing ideal analytical tools to precisely quantify food additives is highly sought after in the food science field. Herein, a new series of quinoline-derived multifunctional fluorescent probes has been synthesized. Bearing double reactive sites, these compounds display fluorescence response toward both bisulfite (HSO 3 − ) and hypochlorous acid (HClO). Among these compact structures, compound ethyl-2-cyano-3-(6-(methylthio)quinolin-2-yl)acrylate (QTE) was screened out. Probe QTE not only shows ratiometric variation toward HSO 3 − with little cross talk but also performs turn-off signal toward HClO. In addition, probe QTE has been utilized for bioimaging of HClO in living cells. Furthermore, the HSO 3 − content in dried food samples has been appraised by QTE with satisfactory results. Meanwhile, relying on the apparent chromaticity change, a flexible dark-box device has been elaborated for chromatic analysis, promoting visualization of HSO 3 − in the field.

show abstract

Section: Resultsmentioning

confidence: 88%

Section: Photophysical Properties and Molecular Screeningmentioning

confidence: 99%

Taming Janus-Faced Quinoline-Derived Fluorescent Probes for Dual-Channel Distinguishable Visualization of HSO₃^– and HClO in Dried Foods and Living Cells

Xu,

Wang,

Xiao

et al. 2024

J. Agric. Food Chem.

View full text Add to dashboard Cite

show abstract

“…The molecular structures of CZ‐Ph‐H , CZ‐Ph‐TA , CZ‐Ph‐CN , and CZ‐Ph‐TB are shown in Figure 1 and the synthesis of the four molecules is included in Supporting Information (Scheme S1). Intermediates 9‐butyl‐9H‐carbazole, [19] 3‐bromo‐9‐butyl‐9H‐carbazole, [20] and compound 1 [21] were synthesized according to previous literature. The target molecules were obtained through bromination, a Suzuki‐Miyaura reaction, and a Knoevenagel reaction.…”

Section: Resultsmentioning

confidence: 99%

Tuning Electronic Structures of Carbazole‐Cyanostyrene Molecules to Achieve Dual‐State Emission for Trace Water Analysis, Picric Acid Sensing, and Reversible Mechanofluorochromism

et al. 2022

View full text Add to dashboard Cite

Dual-state emissive (DSE) materials with efficient emission both in solution and in the solid state can be used in complex environments. In this work, we demonstrate the synthesis of DSE materials by finely tuning the electronic structures of luminogens. Four carbazole-cyanostyrene compounds with different terminal groups, i. e., CZ-Ph-H without additional substituent, CZ-Ph-TA with an N,N-dimethylamino functional group, CZ-Ph-CN with a cyano group, and CZ-Ph-TB with a tbutyl group, have been synthesized and their photophysical properties are fully investigated by spectroscopic studies, theoretical calculations, and crystallographic analysis. Interestingly, while CZ-Ph-H, CZ-Ph-CN, and CZ-Ph-TB are aggregation-induced emissive (AIE) molecules only showing strong emission in the aggregated states (aggregate suspension and solid powder), CZ-Ph-TA is a DSE molecule showing strong emission in both dilute solution and aggregated states. In addition, CZ-Ph-TA could serve as a fluorescent probe for trace water analysis in organic solvents and picric acid (PA) detection in both dilute solution and aggregate suspension. CZ-Ph-TA also exhibits reversible mechanofluorochromism with a spectral shift of 21 nm. The synthesis of the N,N-dimethylamino-substituted molecule with excellent photophysical properties represents an important attempt to achieve DSE by finely tuning the electronic structures of molecules.

show abstract

“…In the design of D–A molecules, carbazole is highlighted as a donor fragment, which has been reported as part of the molecular structure of fluorophores with dual state emission (DSE), 20–22 as well as systems with aggregation induced emission enhancement (AIEE) 23–25 with high fluorescence quantum yields in the solid state ( Φ F = 14–59%) and in the liquid state ( Φ F = 73–100%). 26 It is possible to take advantage of the optical properties of carbazole by including it in the chalcone structure, resulting in band gap values of ∼3.25 eV and an increasing in the ICT.…”

Section: Introductionmentioning

confidence: 99%

Fabrication of photoluminescent nanoparticles from carbazole-derived chalcones: a study of optical properties, cell biomarking, and metabolism

Estrada-Flores¹,

Garcías-Morales²,

Pérez-Berumen³

et al. 2023

Mater. Adv.

View full text Add to dashboard Cite

show abstract

Carbazole-based D-π-A molecules: Determining the photophysical properties and comparing ICT effects of π-spacer and acceptor groups

Cited by 14 publications

References 75 publications

Taming Janus-Faced Quinoline-Derived Fluorescent Probes for Dual-Channel Distinguishable Visualization of HSO₃^– and HClO in Dried Foods and Living Cells

Taming Janus-Faced Quinoline-Derived Fluorescent Probes for Dual-Channel Distinguishable Visualization of HSO₃^– and HClO in Dried Foods and Living Cells

Tuning Electronic Structures of Carbazole‐Cyanostyrene Molecules to Achieve Dual‐State Emission for Trace Water Analysis, Picric Acid Sensing, and Reversible Mechanofluorochromism

Fabrication of photoluminescent nanoparticles from carbazole-derived chalcones: a study of optical properties, cell biomarking, and metabolism

Contact Info

Product

Resources

About

Carbazole-based D-π-A molecules: Determining the photophysical properties and comparing ICT effects of π-spacer and acceptor groups

Cited by 14 publications

References 75 publications

Taming Janus-Faced Quinoline-Derived Fluorescent Probes for Dual-Channel Distinguishable Visualization of HSO3– and HClO in Dried Foods and Living Cells

Taming Janus-Faced Quinoline-Derived Fluorescent Probes for Dual-Channel Distinguishable Visualization of HSO3– and HClO in Dried Foods and Living Cells

Tuning Electronic Structures of Carbazole‐Cyanostyrene Molecules to Achieve Dual‐State Emission for Trace Water Analysis, Picric Acid Sensing, and Reversible Mechanofluorochromism

Fabrication of photoluminescent nanoparticles from carbazole-derived chalcones: a study of optical properties, cell biomarking, and metabolism

Contact Info

Product

Resources

About

Taming Janus-Faced Quinoline-Derived Fluorescent Probes for Dual-Channel Distinguishable Visualization of HSO₃^– and HClO in Dried Foods and Living Cells

Taming Janus-Faced Quinoline-Derived Fluorescent Probes for Dual-Channel Distinguishable Visualization of HSO₃^– and HClO in Dried Foods and Living Cells