Arylene‐Ethynylene Oligomers Based on the Proton Sponge. Issue 42 (6th November 2019)

• Record Type: Journal Article
• Authors: Filatova, Ekaterina A.; Pozharskii, Alexander F.; Gulevskaya, Anna V.; Ozeryanskii, Valery A.; Tsybulin, Semyon V.; Filarowski, Aleksander
• Is Part Of: European journal of organic chemistry. Issue 42(2019)
• Page Start: 7128
• Page End: 7141
• Publication Date: 2019-11-06
• Subjects: Oligo(naphthylene‐ethynylene)s -- Proton sponges -- Proton dynamics -- Synthesis design -- Materials chemistry; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201901292
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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). Abstract : 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.