Synthesis and Characterization of Naphtho[2,1‐b:7,8‐b′]bis[1]benzothiophene

We describe a simple three‐step synthesis of naphtho[2,1‐b:7,8‐b′]bis[1]benzothiophene, which is scalable to multi‐hundred‐gram. We report the subsequent functionalization of this compound into iodine, boronic ester and silane derivatives, which are useful intermediates for various applications. The...

Full description

Saved in:
Bibliographic Details
Published in:European journal of organic chemistry 2020-01, Vol.2020 (1), p.66-69
Main Authors: Kaiser, Jens, Mekic, Amel, Parham, Amir Hossain, Buchholz, Herwig, König, Burkhard
Format: Article
Language:English
Subjects:
Building blocks
Organic electronics
Sulfur heterocycles
Synthetic methods
Upscaling
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:We describe a simple three‐step synthesis of naphtho[2,1‐b:7,8‐b′]bis[1]benzothiophene, which is scalable to multi‐hundred‐gram. We report the subsequent functionalization of this compound into iodine, boronic ester and silane derivatives, which are useful intermediates for various applications. The core structure was analyzed by NMR and single‐crystal X‐ray diffraction, and the physical properties were investigated by cyclic voltammetry, UV/Vis‐ and fluorescence spectroscopy. Naphtho[2,1‐b:7,8‐b′]bis[1]benzothiophene is synthesised in three steps on a multi‐hundred‐gram scale. Subsequent functionalization of the compound yields the iodine, boronic ester and silane derivatives, which are valuable intermediates for subsequent coupling reactions.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201901299