Synthesis, structure, and properties of switchable cross-conjugated 1,4-diaryl-1,3-butadiynes based on 1,8-bis(dimethylamino)naphthalene

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 sy...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2023-05, Vol.19 (1), p.674-686
Main Authors: Tsybulin, Semyon V, Filatova, Ekaterina A, Pozharskii, Alexander F, Ozeryanskii, Valery A, Gulevskaya, Anna V
Format: Article
Language:English
Subjects:
1,4-diaryl-1,3-butadiynes
1,8-bis(dimethylamino)naphthalene
Chemistry
cross-conjugated systems
donor–acceptor systems
Full Research Paper
glaser–hay reaction
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Summary: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.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.19.49