Video Experimental Relacionado

Updated: Mar 28, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

Published on: June 10, 2021

(Z) -1,2-Di ((1-pirenil) disileno: síntesis, estructura y emisión por transferencia de carga intramolecular

Megumi Kobayashi¹, Naoki Hayakawa², Tsukasa Matsuo^1,2,3

¹Functional Elemento-Organic Chemistry Unit, RIKEN Advanced Science Institute , 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.

Journal of the American Chemical Society

|January 5, 2016

Resumen

Los investigadores sintetizaron una nueva molécula de (Z) -1,2-Di ((1-pirenil) disileno con grupos voluminosos de octaetil-s-hidrindaceno (Eind). Esta estructura de engranaje molecular única exhibe fluorescencia de transferencia de carga intramolecular dependiente del disolvente.

Área de la Ciencia:

Química del silicio orgánico
Ciencias de los materiales
La fotofísica

Sus antecedentes:

Los disilenos son análogos de silicio de los alquenos, que ofrecen propiedades electrónicas y estructurales únicas.
Los fenómenos de transferencia de carga intramolecular (TIC) son cruciales para el diseño de materiales funcionales avanzados.
Los sustituyentes estéricamente exigentes a menudo se emplean para estabilizar las especies reactivas de silicio y controlar la arquitectura molecular.

Objetivo del estudio:

Síntesis y caracterización de un nuevo derivado de (Z) -1,2-di ((1-pirenil) disileno con grupos Eind voluminosos.
Investigar la estructura en estado sólido y las propiedades fotofísicas del disileno sintetizado.
Explorar la influencia de los sustituyentes de pirenilo y Eind en el comportamiento electrónico y óptico del núcleo de disileno.

Principales métodos:

Acoplamiento reductivo de un precursor de dibromosilano utilizando naftalenuro de litio.
Difracción de rayos X monocristalino para el análisis estructural detallado.
Absorción UV-Vis y espectroscopia de fluorescencia en varios disolventes.
Estudios computacionales que incluyen cálculos de estado excitado.

Principales resultados:

Síntesis y aislamiento exitosos de (Z) -1,2-Di ((1-pirenil) disileno con grupos Eind en forma de cristales morados.
La cristalografía de rayos X reveló una estructura similar a un engranaje molecular con apilamiento π-π intramolecular entre grupos pirenilo (3.635 Å).
El disileno exhibió fluorescencia TIC a temperatura ambiente (π ((Si-Si) → π * ((pyrene)) sensible a la polaridad del disolvente.

Conclusiones:

Los gruesos grupos de Eind estabilizan efectivamente el núcleo de disileno y hacen cumplir una configuración Z específica.
La fluorescencia TIC observada pone de relieve el potencial de este sistema de disileno para aplicaciones optoelectrónicas.
La interacción entre las interacciones de silicio-π y los sustituyentes voluminosos ofrece una vía para diseñar nuevos materiales de organosilicio.

Más Videos Relacionados

Author Spotlight: Experimental Approaches for the Synthesis of Low-Valent Metal-Organic Frameworks from Multitopic Phosphine Linkers

Author Spotlight: Experimental Approaches for the Synthesis of Low-Valent Metal-Organic Frameworks from Multitopic Phosphine Linkers

Published on: May 12, 2023

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core

Published on: October 24, 2017

Videos de Conceptos Relacionados

Structure of Conjugated Dienes

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...

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.

Hybridization of Atomic Orbitals II

Hybridization of Atomic Orbitals II

sp3d and sp3d 2 Hybridization

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.

Diels–Alder Reaction: Characteristics of Dienes

Diels–Alder Reaction: Characteristics of Dienes

The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable,...

Thermal and Photochemical Electrocyclic Reactions: Overview

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.