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Arylene‐Ethynylene Oligomers Based on the Proton Sponge
Author(s) -
Filatova Ekaterina A.,
Pozharskii Alexander F.,
Gulevskaya Anna V.,
Ozeryanskii Valery A.,
Tsybulin Semyon V.,
Filarowski Aleksander
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901292
Subject(s) - chemistry , arylene , protonation , sonogashira coupling , proton , polymer chemistry , electrochemistry , stereochemistry , crystallography , organic chemistry , ion , palladium , alkyl , physics , quantum mechanics , aryl , catalysis , electrode
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).