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Chemistry of Anthracene–Acetylene Oligomers: Synthesis and Enantiomeric Resolution of a Chiral 1,8‐Anthrylene–Ethynylene Cyclic Tetramer
Author(s) -
Toyota Shinji,
Suzuki Shinya,
Goichi Michio
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200501111
Subject(s) - anthracene , tetramer , chemistry , oligomer , circular dichroism , sonogashira coupling , enantiomer , acetylene , cotton effect , dimer , crystallography , conjugated system , polymer chemistry , stereochemistry , photochemistry , organic chemistry , polymer , enzyme , catalysis , palladium
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.