End‐Capped, Conjugated (Dimethylamino)naphthyl Nanostructures with Alternating (1‐Naphthylethynyl‐p‐phenylethynyl)_x Branches on a 1,3,5‐Substituted Benzene Core

Abstract

Alternating (1‐naphthylethynyl‐p‐phenylethynyl)x 1,3,5‐trisubstituted benzene dendrons were efficiently synthesised by the heterocoupling reaction between (1‐naphthylethynyl‐p‐phenyl)xacetylene (x = 1) and 1,3,5‐triiodobenzene in the presence of a palladium‐copper catalyst system. A longer terminal acetylene chain (x = 2) was obtained from the heterocoupling between 1,3,5‐tri(1‐ethynyl‐5‐naphthylethynyl)benzene and the appropriate iodoaryl derivative. The alternating chains, and their dendron structures, show fluorescence emission, with similar wavelengths and quantum yields. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

Synthesis, Characterization and Properties of 1,4-Bis(Naphthalen-1-Ylethynyl)Benzene and Its Derivatives: Monomers of Oligomers or Polymers Based on Linear 1,4-Phenylethynyl or 1,5-Naphthylethynyl Subunits

“…The naphthalenethynylene-type polymers or oligomers were the outstanding representatives, for different ways can be used to link the naphthalene units [28,29]; e.g., Rodriguez and co-workers have successfully synthesized large numbers of naphthalenethynylene-type oligomers, such as 1,5-naphthalene nanostructures [30,31], 1,5-bis(p-phenylethynyl)naphthalene nanostructures [31] and a series of end-capped, conjugated (dimethylamino) naphthyl nanostructures with alternating (1-naphthylethynyl-p-phenylethynyl) x branches on a 1,3,5-or 1,4substituted benzene core [32][33][34][35], and indicated that these oligomers exhibited excellent quantum yields for the fluorescent emission. However, poor solubility of these oligomers remained the most serious problem.…”