Related Experiment Video
Updated: Jun 1, 2026
08:54
Facile Preparation and Photoactivation of Prodrug-Dye Nanoassemblies
Published on: February 17, 2023
Facile synthesis of highly fluorescent Boranil complexes
Denis Frath1, Sébastien Azizi, Gilles Ulrich
1Laboratoire de Chimie Organique et Spectroscopies Avancées (LCOSA), UMR7515 au CNRS, Ecole de Chimie, Polymères, Matériaux de Strasbourg (ECPM), 25 rue Becquerel, 67087 Strasbourg, Cedex 02, France.
Organic Letters
|June 9, 2011
Summary
Stable Boranils were synthesized from aniline-imines (Anils) and boron(III) precursors. Their fluorescence originates from an intraligand charge transfer (ILCT) state, achieving high quantum yields up to 90%.
Area of Science:
- * Inorganic Chemistry
- * Materials Science
- * Photophysics
Background:
- * Aniline-imines (Anils) are versatile organic ligands.
- * Boron(III) complexes offer unique electronic and optical properties.
- * Understanding structure-property relationships in novel boron compounds is crucial.
Purpose of the Study:
- * To synthesize and characterize novel Boranil compounds.
- * To investigate the photophysical properties, specifically fluorescence, of Boranils.
- * To explore chemical modifications of Boranils for advanced applications.
Main Methods:
- * Complexation reactions between various Anils and boron(III) precursors.
- * Structural characterization of selected Boranil complexes.
- * Spectroscopic analysis to determine optical properties and fluorescence quantum yields.
Main Results:
- * Successful synthesis of a diverse range of stable Boranils.
- * Identification of intraligand charge transfer (ILCT) as the primary fluorescence mechanism.
- * Achieved high fluorescence quantum yields, up to 90%.
- * Demonstrated successful grafting of photoactive modules (Bodipy, SubPc) onto Boranils.
Conclusions:
- * Boranils represent a promising class of fluorescent materials.
- * The ILCT state is key to their efficient fluorescence.
- * Boranils can be functionalized to create advanced photoactive systems.
More Related Videos
Related Concept Videos
01:13Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
03:08Hydroboration-Oxidation of Alkenes
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
01:14Photoluminescence: Applications
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...
01:26Variables Affecting Phosphorescence and Fluorescence
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...
02:47Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.