Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

3.7K
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,...
3.7K
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

5.7K
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
5.7K
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

2.3K
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.
2.3K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

2.7K
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...
2.7K
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

10.2K
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?  
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as...
10.2K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

2.7K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
2.7K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Risk prediction models for cognitive impairment in patients with chronic kidney disease: a systematic review.

Frontiers in public health·2026
Same author

Mechanical force awakens dormant catalyst: Piezocatalytic CO<sub>2</sub> reduction outperforms photocatalysis by over two orders of magnitude.

Journal of colloid and interface science·2026
Same author

Design Principles for Nanobubble Regulation on Electrocatalytic Interfaces.

The journal of physical chemistry letters·2026
Same author

Diagnostic yield and feasibility of EBUS-guided cautery-assisted transbronchial forceps biopsy for suspected benign mediastinal and hilar lymphadenopathy: a prospective self-controlled pilot study.

BMC pulmonary medicine·2026
Same author

Serum DSDNA is Associated With Psoriasis.

Experimental dermatology·2026
Same author

Multi-scale analysis of seed dormancy in Lonicera maackii and functional identification of LmABI5 in promoting dormancy.

Plant science : an international journal of experimental plant biology·2026
Same journal

Y(OTf)<sub>3</sub>-Catalyzed Formal (3 + 2) Cycloadditions of Donor-Acceptor Cyclopropanes with KSCN under Mechanochemical Conditions.

Organic letters·2026
Same journal

Electro-Mediated Regioselective C2-Alkylation of <i>N</i>-Oxide Heteroarenes.

Organic letters·2026
Same journal

Organophosphine-Promoted Decarbynylative Hydrocarbenylation of the Carbon-Carbon Triple Bond.

Organic letters·2026
Same journal

Total Syntheses of BE-54238A and -B.

Organic letters·2026
Same journal

Visible Light-Induced <i>N</i>-Phenylbenzo[<i>c</i>]phenothiazine-Catalyzed α-C(sp<sup>3</sup>)-H Phosphonylation of Secondary Amines via Intramolecular 1,5-HAT.

Organic letters·2026
Same journal

Cobalt-Stabilized Propargylic Oxocarbenium Ions Enable Direct and Asymmetric Nickel(II) Catalyzed Aldol-Like Reactions.

Organic letters·2026
See all related articles

Related Experiment Video

Updated: Jun 5, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

11.4K

Heterocoronenes Containing Pyridine and 1,2-Azaborine Units.

Ruili Li1, Xiaohong Lin1, Changhua Ding1

  • 1Department of Chemistry, College of Sciences, Shanghai University, Shanghai 200444, China.

Organic Letters
|December 9, 2024
PubMed
Summary
This summary is machine-generated.

Researchers synthesized novel coronenes with pyridine and azaborine units. These materials exhibit unique BN-H---N hydrogen bonds and dual sensing capabilities for fluoride and protons.

More Related Videos

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants
08:56

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

Published on: March 25, 2017

7.6K
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

6.2K

Related Experiment Videos

Last Updated: Jun 5, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

11.4K
Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants
08:56

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

Published on: March 25, 2017

7.6K
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

6.2K

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Polycyclic aromatic hydrocarbons (PAHs) are crucial in organic electronics.
  • Incorporating heteroatoms like nitrogen and boron can tune electronic properties.
  • Understanding intermolecular interactions is key for material design.

Purpose of the Study:

  • To synthesize novel coronene derivatives incorporating pyridine and azaborine units.
  • To investigate the structural, electronic, and sensing properties of these new materials.
  • To explore the formation of non-covalent interactions in boron-nitrogen polycyclic aromatic hydrocarbons (BN-PAHs).

Main Methods:

  • Chemical synthesis of coronene derivatives.
  • X-ray crystallographic analysis for structural confirmation.
  • Spectroscopic and electrochemical techniques to study electronic properties.
  • Solution-based assays to evaluate sensing capabilities.

Main Results:

  • Successful synthesis and structural verification of pyridine- and azaborine-containing coronenes.
  • First observation of BN-H---N hydrogen bonds in BN-PAH crystals.
  • Short π-π stacking distances facilitating intermolecular electronic coupling.
  • Lowered Highest Occupied Molecular Orbital-Lowest Unoccupied Molecular Orbital (HOMO-LUMO) levels and a narrow band gap.
  • Unique dual sensing response to fluoride ions and protons in solution.

Conclusions:

  • The incorporation of pyridine and azaborine units into coronene frameworks yields materials with tunable electronic properties.
  • The identified BN-H---N hydrogen bonds play a significant role in crystal packing and material properties.
  • These novel BN-PAHs demonstrate potential for applications in sensing technologies due to their selective dual response.