Suzuki Coupling of Chiral 1,1′-Binaphthyl Systems − New Synthetic Routes to Functionalize the 2- and 2,2′-Positions

Abstract

1,1′‐Binaphthyl derivatives 1‐5, substituted in the 2‐ or 2,2′‐positions are used in palladium‐catalyzed Suzuki coupling reactions. The mono‐ and bis‐borylated coupling components 2, 4 and 5 can easily be prepared and purified, are air‐stable and are therefore interesting starting materials for Suzuki coupling reactions with several aryl halides. Thus a variety of new axially‐chiral 2‐ and 2,2′‐arylated 1,1′‐binaphthyls can be synthesized. Selective monoarylation of 3, 4 and 5 can be performed. Subsequent and stepwise arylation offers general access to unsymmetrically substituted binaphthyls. Moreover, interesting atropisomeric complex molecules, such as 4,4′‐bis[2‐(1,1′‐binaphthyl)]‐1,1′‐biphenyl (18a), are accessible. Compounds of type 18, which can be obtained by twofold Pd‐catalyzed coupling reactions, are of high potential value as ligands or promoters in catalytic, asymmetric processes or as chiral precursor molecules for host‐guest interactions.

Alkyl and allyl substituted polydibenzofluorene: blue emitters for future display applications

“…Conjugated polymers were the basis for comprehensive research in strongly conjugated organic polymers. Many conjugated polymers with various optical, electrical, and magnetic properties have been synthesized for display applications [5][6][7]. Poly(phenylenevinylene) (PPV), poly(2,7-(9,9-dialkyl)fluorene)s (PFs) and their derivatives have gained considerable attention in recent decades as a promising substrate for full-color flat panel display [8].…”