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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

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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.
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Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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Variables Affecting Phosphorescence and Fluorescence01:26

Variables Affecting Phosphorescence and Fluorescence

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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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Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

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Like benzene, cyclobutadiene and cyclooctatetraene are cyclic compounds with alternate single and double bonds. However, their chemical behavior differs from benzene, as they are unstable and not aromatic. So, what are the structural characteristics of unsaturated compounds categorized as aromatic?  
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Halogens03:01

Halogens

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Group 17 elements, known as halogens, are nonmetals. At room temperature, fluorine and chlorine are gases, bromine is a liquid, and iodine a solid. Astatine is a highly unstable radioactive element, so currently, most of its properties are unknown due to its short half-life. Tennessine is a synthetic element also predicted to be in this group. 
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Related Experiment Video

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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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Bis-(Fluorene)-Embedded Hexaphyrins.

Bharti Yadav1, Mangalampalli Ravikanth1

  • 1Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.

The Journal of Organic Chemistry
|February 16, 2022
PubMed
Summary

New bis-(fluorene)-embedded hexaphyrins, a type of expanded porphyrin, were synthesized and characterized. These flexible macrocycles exhibit unique electronic and structural properties, confirmed by spectroscopic and computational methods.

Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Expanded porphyrins, including hexaphyrins, are macrocyclic compounds with unique photophysical and electronic properties.
  • Incorporating polyaromatic hydrocarbon moieties like fluorene can significantly tune these properties.

Purpose of the Study:

  • To synthesize novel bis-(fluorene)-embedded hexaphyrins.
  • To characterize their structural, optical, and electrochemical properties.
  • To investigate the influence of fluorene units on the macrocycle's conjugation and flexibility.

Main Methods:

  • Synthesis via condensation of fluorene-based tripyrrane with pentafluorobenzaldehyde, followed by oxidation.
  • Characterization using High-Resolution Mass Spectrometry (HRMS) and Nuclear Magnetic Resonance (NMR) spectroscopy.

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  • Spectroscopic (absorption), electrochemical, and computational (Density Functional Theory/Time-Dependent DFT) analyses.

    • Main Results:

    • Successful synthesis of bis-(fluorene)-embedded hexaphyrins under specific reaction conditions.
    • NMR studies revealed significant flexibility at room temperature, with well-resolved spectra at lower temperatures.
    • DFT calculations indicated a non-planar structure with one fluorene unit largely detached from conjugation.
    • Absorption spectra showed distinct high and low-energy bands, characteristic of expanded porphyrins.
    • Electrochemical studies demonstrated electron-rich behavior with multiple oxidation and reduction potentials.

    Conclusions:

    • The synthesized hexaphyrins possess unique structural and electronic characteristics due to the embedded fluorene units.
    • The flexibility and partial conjugation impact their photophysical and electrochemical behavior.
    • These findings contribute to the understanding of structure-property relationships in expanded porphyrin systems.