Chemistry of Anthracene–Acetylene Oligomers: Synthesis and Enantiomeric Resolution of a Chiral 1,8-Anthrylene–Ethynylene Cyclic Tetramer

✍ Scribed by Shinji Toyota; Shinya Suzuki; Michio Goichi

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 262 KB
• Volume: 12
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.200501111

✦ Synopsis

Abstract

To construct a new type of chiral π‐conjugated system, the title anthracene–acetylene oligomer containing two octyl groups at position 10 of 1,2‐alternating anthracene groups was synthesized. Each anthracene unit was connected by Sonogashira coupling, and the tetrameric precursor was cyclized by a cross‐coupling reaction to form the desired C~2~‐symmetric compound. Its enantiomers were resolved by chiral HPLC with a Chiralcel OD column, and the chiroptical properties were investigated by optical rotation ([α]${{{23\hfill \atop {\rm D}\hfill}}}$=−95 and +91) and circular dichroism (CD) measurements. The structural and spectroscopic features of this oligomer were discussed in terms of the molecular symmetry and the dynamic behavior of the macrocyclic framework.