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Photoluminescence: Applications01:14

Photoluminescence: Applications

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Photoluminescence offers a wide range of applications due to its inherent sensitivity and selectivity. This technique allows for both direct and indirect analyses of the analyte. Direct quantitative analysis is possible when the analyte exhibits a favorable quantum yield for fluorescence or phosphorescence. However, an indirect analysis may be feasible if the analyte is not fluorescent or phosphorescent, or if the quantum yield is unfavorable. Indirect methods include reacting the analyte with...
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Variables Affecting Phosphorescence and Fluorescence01:26

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Fluorescence and phosphorescence are essential phenomena in fields like analytical chemistry, biological imaging, and materials science, where they detect molecular properties and visualize cellular structures. Understanding the variables that influence these luminescent behaviors is crucial for maximizing accuracy and efficiency in their applications. These variables can broadly be grouped into chemical structure, solvent properties, and external conditions, each playing a distinct role in...
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Photoluminescence: Fluorescence and Phosphorescence01:23

Photoluminescence: Fluorescence and Phosphorescence

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Photoluminescence is a process where a molecule absorbs light energy and re-emits it in the form of light. This phenomenon occurs when a substance absorbs photons, promoting its electrons to higher energy level excited states, followed by a relaxation process in which the electrons return to their original ground state energy levels and emit light. Photoluminescence is widely observed in various materials, including semiconductors, and organic and inorganic compounds.
A pair of electrons in a...
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Fluorescence and Phosphorescence: Instrumentation01:25

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Fluorometers and spectrofluorometers are two types of instruments used for measuring molecular fluorescence. These instruments differ in how they select excitation and emission wavelengths and the type of light sources they utilize. Fluorometers use absorption interference filters to choose excitation and emission wavelengths. The excitation source in a fluorometer is typically a low-pressure mercury vapor lamp that emits intense lines distributed throughout the ultraviolet and visible regions.
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2° Amines to N-Nitrosamines: Reaction with NaNO2

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Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Naphthalonitriles featuring efficient emission in solution and in the solid state.

Sidharth Thulaseedharan Nair Sailaja1,2, Iván Maisuls1,2, Jutta Kösters1

  • 1Institut für Anorganische und Analytische Chemie, Westfälische Wilhelms-Universität Münster, Corrensstraße 28/30, 48149 Münster, Germany.

Beilstein Journal of Organic Chemistry
|December 18, 2020
PubMed
Summary
This summary is machine-generated.

Researchers synthesized novel diphenylnaphthalonitriles with tunable emission properties. Their fluorescence color shifts based on substituent electronic effects and aggregation, showing potential for advanced applications.

Keywords:
aggregation caused quenching (ACQ)aggregation-induced emission enhancement (AIEE)naphthalonitriles (NCNs)solution and solid state emitters (SSSE)solvent quenching (SQ)

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Photophysics

Background:

  • Developing luminescent materials with tunable emission is crucial for advanced technologies.
  • Understanding structure-property relationships in organic fluorophores guides material design.
  • Environmental sensitivity of photophysical properties is key for sensing applications.

Purpose of the Study:

  • To synthesize and characterize a series of γ-substituted diphenylnaphthalonitriles.
  • To investigate the influence of substituents on photophysical properties in solution and aggregated states.
  • To explore the environmental responsiveness of these novel luminescent materials.

Main Methods:

  • Synthesis and characterization of γ-substituted diphenylnaphthalonitriles.
  • Steady-state and time-resolved photoluminescence spectroscopy in tetrahydrofuran (THF) and THF/water mixtures.
  • Dynamic light scattering (DLS) for aggregate size analysis.
  • Crystal structure analysis of a representative compound.

Main Results:

  • Synthesized compounds exhibit efficient fluorescence in both solution and aggregated states.
  • Substituent electronic properties (π-donor capability) dictate emission color, ranging from blue to red.
  • Aggregation in aqueous media induces environment-specific emission shifts (red-shift for weak donors, blue-shift for strong donors).
  • Dimethylamino (NMe2) substituents yield higher luminescence quantum yields compared to methylsulfanyl (SMe) groups.

Conclusions:

  • The π-donor nature of substituents is the primary factor controlling photophysical properties.
  • These diphenylnaphthalonitriles offer tunable emission and environmental sensitivity.
  • The developed materials hold promise for applications in sensing, bioimaging, and optoelectronics.