Yamamoto Coupling for the Synthesis of Benzophenes and Acene-Based Cyclooctatetraenes.

Elias C RüdigerSilke KoserFrank RomingerJan FreudenbergUwe H F Bunz

Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2018)

Two TIPS-ethynylated dibromoacenes were used in a shotgun Yamamoto-reaction with 1,2-dibromobenzene or 4,5-dibromoveratrol. Four soluble benzononaphenes/benzoundecaphenes were isolated in satisfactory yields. Examples of tetracene- and pentacene-fused tetrabenzocyclooctatetraenes also isolated from this reaction are reported. All compounds were characterized by UV/Vis and fluorescence spectroscopy, cyclic voltammetry, X-ray crystallography as well as DFT and NICS calculations.

Keyphrases

density functional theory
high resolution
single molecule
electron transfer
molecular dynamics
molecular dynamics simulations
molecular docking
room temperature
dual energy
computed tomography
energy transfer
magnetic resonance imaging
mass spectrometry
quantum dots
ionic liquid