Related Experiment Video
Updated: Apr 26, 2026
09:46
Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores
Published on: August 19, 2013
13.7K
Aliphatic amine discrimination by pentafluorophenyl dibromo BODIPY
Adiki Raja Sekhar1, Masood Ayoub Kaloo, Jeyaraman Sankar
1Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Indore bypass road, Bhouri, Bhopal, 462066 (India), Fax: (+91) 755-6692392.
Chemistry, an Asian Journal
|July 22, 2014
Summary
New BODIPY dyes offer unprecedented dual-mode detection for primary, secondary, and tertiary aliphatic amines. This colorimetric and fluorescent method provides instantaneous recognition, advancing chemical sensing technologies.
Area of Science:
- Organic Chemistry
- Analytical Chemistry
- Materials Science
Background:
- Boron-dipyrromethene (BODIPY) dyes are widely used due to their strong fluorescence and tunable properties.
- Selective detection of aliphatic amines is crucial in various fields, including environmental monitoring and chemical synthesis.
- Existing methods for amine detection often lack selectivity or require complex procedures.
Purpose of the Study:
- To design and synthesize novel fluorescent BODIPY dyes.
- To investigate the selective reactivity of these dyes with different classes of aliphatic amines.
- To establish a dual-mode (colorimetric and fluorescent) sensing platform for amine discrimination.
Main Methods:
- Synthesis of two new BODIPY dyes with varying meso substituents.
- Exploration of their reactivity via an Ar-S(N)2 reaction mechanism.
- Spectroscopic analysis (UV-Vis absorption and fluorescence emission) to monitor the recognition events.
Main Results:
- Successful synthesis of two novel BODIPY dyes with distinct electronic properties.
- Demonstration of selective reactivity of the BODIPY dyes towards primary, secondary, and tertiary aliphatic amines.
- Observation of instantaneous colorimetric and fluorescent changes upon amine interaction, enabling dual-mode detection.
Conclusions:
- The developed BODIPY dyes serve as effective chemosensors for discriminating aliphatic amines.
- The unprecedented dual-mode, instantaneous recognition offers a significant advancement in amine sensing technology.
- This platform holds potential for developing rapid and selective analytical tools for amine detection.
More Related Videos
Related Concept Videos
01:18Basicity of Aromatic Amines
7.7K
The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...
7.7K
01:26Physical Properties of Amines
3.2K
Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
3.2K
01:13Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
6.5K
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.
6.5K
01:19NMR Spectroscopy Of Amines
9.9K
In proton NMR spectroscopy, primary amines and secondary amines showcase their N–H protons as a broad signal in the chemical shift range between δ 0.5 and 5 ppm. The exact position in this range depends on several factors, including sample concentration, hydrogen bonding, and the type of solvent used. Since amine protons undergo fast proton exchange in solution, the protons are labile and therefore do not participate in any splitting with adjacent protons. Thus, the observed peak is...
9.9K
01:10Nomenclature of Aryl and Heterocyclic Amines
2.2K
The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
2.2K
01:17Nomenclature of Primary Amines
3.7K
Primary, secondary, and tertiary amines are compounds consisting of one, two, and three alkyl groups connected to the amino group (–NH2), respectively. As depicted in Figure 1, the common name of the primary amines is obtained by adding the suffix -amine to the alkyl substituent attached to the amino group as the corresponding alkylamine.
3.7K