Arylene‐Ethynylene Oligomers Based on the Proton Sponge

A new family of arylene‐ethynylene oligomers consisting of two, three and four “proton sponge” fragments (1,8‐bis(dimethylamino)naphthalene or DMAN) alternating with C≡C bonds were synthesized using various 2‐ and 4‐ethynyl and 2‐ and 4‐iodo derivatives of DMAN as synthetic building blocks in the So...

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Bibliographic Details
Published in:European journal of organic chemistry 2019-11, Vol.2019 (42), p.7128-7141
Main Authors: Filatova, Ekaterina A., Pozharskii, Alexander F., Gulevskaya, Anna V., Ozeryanskii, Valery A., Tsybulin, Semyon V., Filarowski, Aleksander
Format: Article
Language:English
Subjects:
Construction materials
Electrochemical analysis
Electron conductivity
Materials chemistry
Naphthalene
Oligo(naphthylene‐ethynylene)s
Oligomers
Organic chemistry
Proton dynamics
Proton sponges
Protonation
Protons
Synthesis design
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Summary:A new family of arylene‐ethynylene oligomers consisting of two, three and four “proton sponge” fragments (1,8‐bis(dimethylamino)naphthalene or DMAN) alternating with C≡C bonds were synthesized using various 2‐ and 4‐ethynyl and 2‐ and 4‐iodo derivatives of DMAN as synthetic building blocks in the Sonogashira coupling. X‐ray structural, photophysical, chemical and electrochemical properties showed that the oligomers are promising candidates to construct materials with varied rigidity (tuned by protonation), electron conductivity (tuned by mode of linkage), and proton conductivity (equilibration of protonated and free DMAN subunits). A new family of arylene‐ethynylene oligomers consisting of two, three, and four “proton sponge” fragments alternating with C≡C bonds were synthesized. X‐ray structural, photophysical, chemical, and electrochemical properties of the oligomers were investigated.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201901292