Novel Chiral Macrocycles Containing Two Electronically Interacting Arylene Chromophores

✍ Scribed by Bernhard Köhler; Volker Enkelmann; Masao Oda; Silvia Pieraccini; Gian Piero Spada; Ullrich Scherf

• Publisher: John Wiley and Sons
• Year: 2001
• Tongue: English
• Weight: 110 KB
• Volume: 7
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/1521-3765(20010716)7:14<3000::aid-chem3000>3.0.co;2-2

✦ Synopsis

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 aw-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 ªintrarodº helicity of individual oligoarylene rods and the ªinter-rodº 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 ªintra-rodº 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 p ± p interactions.