Enhanced yet Inverted Effects of π-Extension in Self-Assembly of Curved π-Systems with Helicity

Taisuke Matsuno1, Kanako Kogashi2, Sota Sato1

  • 1Department of Chemistry, The University of Tokyo and JST, ERATO, Isobe Degenerate π-Integration Project , Hongo 7-3-1, Bunkyo-ku, Tokyo 113-0033, Japan.

Organic Letters
|November 22, 2017
PubMed

Related Concept Videos

Determination of Pi Terms01:15

Determination of Pi Terms

The Buckingham Pi theorem is a valuable method in dimensional analysis, reducing complex relationships between variables into dimensionless terms. Relevant variables in analyzing the lift force on an airplane wing include lift force, air density, wing area, aircraft velocity, and air viscosity. Expressing each variable in terms of fundamental dimensions — mass, length, and time — provides a consistent foundation for constructing these dimensionless terms.
The theorem indicates that the...
636
Thermal Sigmatropic Reactions: Overview01:16

Thermal Sigmatropic Reactions: Overview

Sigmatropic rearrangements are a class of pericyclic reactions in which a σ bond migrates from one part of a π system to another. These are intramolecular rearrangements where the total number of σ and π bonds remain unchanged.
Sigmatropic shifts are classified based on an order term [i, j ], where i and j indicate the number of atoms across which each end of the σ bond migrates. Below are examples of a [3,3] sigmatropic shift in 1,5-hexadiene, referred...
2.6K
π Electron Effects on Chemical Shift: Overview01:27

π Electron Effects on Chemical Shift: Overview

An applied magnetic field causes loosely bound π-electrons in organic molecules to circulate, producing a local or induced diamagnetic field over a large spatial volume. As the molecules tumble in solution, the field generated by π-electrons in spherical substituents results in a zero net field. However, the net field generated by π-electrons in non-spherical substituents is not zero. The effect of this induced field depends on the orientation of the molecule with respect to B0,...
1.7K
Deformations in a Symmetric Member in Bending01:18

Deformations in a Symmetric Member in Bending

When analyzing the deformation of a symmetric prismatic member subjected to bending by equal and opposite couples, it becomes clear that as the member bends, the originally straight lines on its wider faces curve into circular arcs, with a constant radius centered at a point known as Point C. This phenomenon helps to understand the stress and strain distribution within the member more clearly.
When the member is segmented into tiny cubic elements, it is observed that the primary stress...
536
Fischer Projections02:18

Fischer Projections

Learning to draw Fischer projections of molecules and understanding their relevance plays a crucial role in the visual depiction of organic molecules. A Fischer projection is a two-dimensional projection on a planar surface to simplify the three-dimensional wedge–dash representation of molecules. This is especially helpful in the case of molecules with multiple chiral centers that can be difficult to draw. Here, all the bonds of interest are represented as horizontal or vertical lines. While...
16.7K
π Molecular Orbitals of 1,3-Butadiene01:24

π Molecular Orbitals of 1,3-Butadiene

Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...
12.1K