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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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 with both...
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).
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.
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

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 Hückel’s rule or the 4n + 2 rule.

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TIPS-benzene-based two-dimensional perovskites.

Naoyuki Nishimura1, Takurou N Murakami1

  • 1National Institute of Advanced Industrial Science and Technology (AIST), 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan. naoyuki-nishimura@aist.go.jp.

Chemical Communications (Cambridge, England)
|May 26, 2026
PubMed
Summary
This summary is machine-generated.

Researchers synthesized novel triisopropylsilylethynyl (TIPS)-benzene-based amines and perovskites. This work demonstrates the use of TIPS-based ions in perovskite crystal lattices for the first time, advancing materials science.

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Crystallography

Background:

  • Organic-inorganic hybrid perovskites are a versatile class of materials with tunable properties.
  • Triisopropylsilylethynyl (TIPS) moieties offer unique steric and electronic characteristics.
  • Integrating novel organic components into perovskite structures is crucial for expanding their applications.

Purpose of the Study:

  • To synthesize novel triisopropylsilylethynyl (TIPS)-benzene-based amines.
  • To develop new two-dimensional organic-inorganic hybrid perovskites incorporating these TIPS-based ammoniums.
  • To demonstrate the applicability of TIPS-based ions within perovskite crystal lattices.

Main Methods:

  • Chemical synthesis of TIPS-benzene-based amines.
  • Crystallization techniques for forming two-dimensional organic-inorganic hybrid perovskites.
  • Structural characterization of the synthesized perovskite materials.

Main Results:

  • Successful synthesis of a novel TIPS-benzene-based amine.
  • Formation of two-dimensional organic-inorganic hybrid perovskites containing TIPS-benzene-based ammonium cations.
  • Experimental validation of the incorporation of TIPS-based ions into the perovskite crystal lattice.

Conclusions:

  • The study establishes the first demonstration of TIPS-based component ions in perovskite crystal lattices.
  • This research promotes advancements in TIPS chemistry and the development of functional materials leveraging TIPS moiety characteristics.
  • The findings contribute to the broader field of perovskite materials science and engineering.