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Updated: Jul 29, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Synthesis, structure, and properties of switchable cross-conjugated 1,4-diaryl-1,3-butadiynes based on
Semyon V Tsybulin1, Ekaterina A Filatova1, Alexander F Pozharskii1
1Department of Chemistry, Southern Federal University, Zorge str. 7, Rostov-on-Don 344090, Russian Federation.
Abstract:
A set of novel 1,4-diaryl-1,3-butadiynes terminated by two 7-(arylethynyl)-1,8-bis(dimethylamino)naphthalene fragments was prepared via the Glaser-Hay oxidative dimerization of 2-ethynyl-7-(arylethynyl)-1,8-bis(dimethylamino)naphthalenes. The oligomers synthesized in this way are cross-conjugated systems, in which two conjugation pathways are possible: π-conjugation of 1,8-bis(dimethylamino)naphthalene (DMAN) fragments through a butadiyne linker and a donor-acceptor aryl-C≡C-DMAN conjugation path. The conjugation path can be "switched" simply by protonation of DMAN fragments. X-ray diffraction, UV-vis spectroscopy and cyclic voltammetry are applied to analyze the extent of π-conjugation and the efficiency of particular donor-acceptor conjugation path in these new compounds. X-ray structures and absorption spectra of doubly protonated tetrafluoroborate salts of the oligomers are also discussed.
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