Related Experiment Video
Updated: Apr 9, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Electron-Deficient Tetrabenzo-Fused Pyracylene and Conversions into Curved and Planar π-Systems Having Distinct
Chaolumen1, Michihisa Murata2, Yasunori Sugano1
1Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan).
Abstract:
Polycyclic aromatic compounds containing fully unsaturated five-membered ring(s) have been intensively studied because of their unique properties, which include high electron affinity and reactivity. Reported herein is an efficient route for the synthesis of tetrabenzo-fused pyracylene, which comprises pyracylene and tetracene segments, using intramolecular oxidative C-H coupling. It was shown to possess high electron affinity and was found to undergo addition reactions with n-butyllithium or benzyne. These reactions led to either a 1,4-addition compound or triptycene-type adduct with a curved or planar π-system, respectively. Although these compounds exhibited similar sky-blue emissions in a dilute solution, the emission band of the 1,4-addition compound was significantly red-shifted in the solid state and exhibited intense yellow emission attributable to the excimer, while the triptycene-type adduct retained the intense blue color emission in the solid state.
More Related Videos
09:17Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes
Published on: January 30, 2015
11:44Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds
Published on: October 18, 2018
Related Concept Videos
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group...
Thermal and Photochemical Electrocyclic Reactions: Overview
Five-Membered Heterocyclic Aromatic Compounds: Overview
Aromatic Hydrocarbon Anions: Structural Overview
Due to the absence of continuous...
π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds