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Related Concept Videos

Structure of Benzene: Kekulé Model01:07

Structure of Benzene: Kekulé Model

In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
Directing and Steric Effects in Disubstituted Benzene Derivatives01:18

Directing and Steric Effects in Disubstituted Benzene Derivatives

When disubstituted benzenes undergo electrophilic substitution, the product distribution depends on the directing effect of both substituents. When the directing effects of both substituents reinforce each other, a single product is obtained. For example, bromination of p-nitrotoluene occurs ortho to the methyl group and meta to the nitro group, which is the same position, resulting in a single product. However, if the directing effects of the two groups oppose each other, the more strongly...
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...

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Related Experiment Video

Updated: Jun 12, 2026

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

BN-Embedded Dibenzoullazine: Synthesis, Structures, and Properties.

Yiqing Liu1, Hui Qi1, Xiaojie Zhang2

  • 1Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion, School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384, People's Republic of China.

Organic Letters
|June 11, 2026
PubMed
Summary
This summary is machine-generated.

We synthesized bis-BN-embedded dibenzoullazine (BNDBU) in five steps. BNDBU-based organic photodetectors demonstrate excellent performance with ultra-low dark current and high on/off ratio.

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Published on: June 23, 2023

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Photodetector Technology

Background:

  • Dibenzoullazine derivatives are explored for optoelectronic applications.
  • Efficient synthesis of novel heterocyclic compounds is crucial for materials development.

Purpose of the Study:

  • To develop a concise synthesis for bis-BN-embedded dibenzoullazine (BNDBU).
  • To investigate the photophysical properties of BNDBU and its saturated analogs.
  • To evaluate BNDBU performance in organic photodetectors.

Main Methods:

  • A five-step synthesis involving ring-closing metathesis and dehydrogenation.
  • Isolation and characterization of BNDBU, f-BNDBU, and p-BNDBU.
  • Systematic investigation of photophysical properties.
  • Fabrication and testing of bulk heterojunction organic photodetectors.

Main Results:

  • A five-step synthesis of BNDBU was successfully achieved.
  • Fully saturated (f-BNDBU) and partially saturated (p-BNDBU) species were isolated.
  • BNDBU-based photodetectors exhibited an ultralow dark current density (6.01 × 10-9 A cm-2) and a high on/off ratio (5.89 × 104).

Conclusions:

  • The developed synthetic route provides efficient access to BNDBU.
  • BNDBU demonstrates promising photophysical properties for optoelectronic applications.
  • BNDBU is a competitive material for self-powered organic photodetectors.