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Novel Chiral Macrocycles Containing Two Electronically Interacting Arylene Chromophores
Author(s) -
Köhler Bernhard,
Enkelmann Volker,
Oda Masao,
Pieraccini Silvia,
Spada Gian Piero,
Scherf Ullrich
Publication year - 2001
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 - 10.1002/1521-3765(20010716)7:14<3000::aid-chem3000>3.0.co;2-2
Subject(s) - chromophore , mesogen , liquid crystal , materials science , helicity , arylene , crystallography , photochemistry , chemistry , liquid crystalline , optoelectronics , alkyl , physics , aryl , organic chemistry , particle physics
Novel chiral macrocycles consisting of two rigid oligoarylene rods and two chiral spiroindane clips have been synthesized by condensation of spiroindane diols and CF 3 ‐activated α ‐ ω ‐difluorooligoaryls. Since a broad variety of planar aromatic macrocycles is known, our non‐planar, chiral rings represent a new class of macrocyclic compounds. The first two examples, which contain quaterphenylene and diphenylbithiophene rods, are presented in this communication; for one of them a crystal structure is given. The chiroptical properties of the macrocycles can be interpreted as an interplay of the “intra‐rod” helicity of individual oligoarylene rods and the “inter‐rod” helicity between both chromophores of the macrocycle. The macrocycles can act as chiral dopands of commercially available, and novel, polymeric nematic liquid crystals (emissive polyfluorenes). The “intra‐rod” helicity of individual oligoarylene rods is the main feature in determining the resulting helical twisting power (HTP). The cholestric induction in mesogenic, emissive polyfluorenes is of special interest for a realization of electronic devices that have a circularly polarized electroluminescence. The results are also important for an understanding of larger ensembles of chiral rodlike molecules, especially their π–π interactions.