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Synthesis of the end-capped 5-(N,N-dimethylamino)naphthyl-1-ethynyl derivatives and their 1,4-di[5-(N,N-dimethylamino)naphthyl]-1,3-butadiynes:antirotamer structure

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
61
Issue
12
Identifiers
DOI: 10.1016/j.tet.2005.01.109
Keywords
  • 1
  • 4-Di[5-(N
  • N-Dimethylamino)Naphthyl]-1
  • 3-Butadiynes
  • X-Ray Structure
  • Sonogashira Reaction
  • Fluorescence

Abstract

Abstract A new family of the end-capped 5-( N, N-dimethylamino)naphthylethynyl chains were synthesized, as terminal acetylenes or poly(yne) structures, by heterocoupling between 5-iodo- N, N-dimethylnaphthalen-1-amine and 2-methyl-3-butyn-2-ol or 4-(5-iodo-1-naphthyl)-2-methyl-3-butyn-2-ol, catalyzed by the palladium–copper system. Catalytic homocoupling of the terminal acetylenes, affords to 1,4-dinaphthyl-1,3-butadiyne nanostructures. X-ray diffraction analysis of 1,4-di(α-naphthyl)-1,3-butadiyne shows that the naphthalene rings are in the anti configuration along the acetylene axis. All the conjugated compounds show an important fluorescent emission radiation.

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