A novel generation of 7-aryl phenothiazinyl substituted polyacetylenes is readily accessible controlled rhodium-catalyzed polymerization of the corresponding 3-ethynyl 7-aryl phenothiazines. The monomers are synthesized by Suzuki coupling, Heck coupling, or Buchwald-Hartwig amination, and Bestmann-Ohira reaction. This allows for the introduction of electron donating and releasing substituents with different ligation patterns. The obtained polymers display narrow molecular weight distributions, with very few exceptions, and are soluble in many organic solvents. The photophysical properties of novel monosubstituted polyacetylenes and corresponding monomers were compared. While the monomers exhibit strong emission in solution with quantum yields of up to 0.84 only selected polymers are luminescent ( = 0.06) and display moderate Stokes shifts and positive emission solvatochromism.
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http://dx.doi.org/10.1039/d4ra01912a | DOI Listing |
RSC Adv
March 2024
Heinrich Heine University Düsseldorf, Faculty of Mathematics and Natural Sciences, Institute of Organic Chemistry and Macromolecular Chemistry Universitätsstrasse 1 D-40225 Düsseldorf Germany
A novel generation of 7-aryl phenothiazinyl substituted polyacetylenes is readily accessible controlled rhodium-catalyzed polymerization of the corresponding 3-ethynyl 7-aryl phenothiazines. The monomers are synthesized by Suzuki coupling, Heck coupling, or Buchwald-Hartwig amination, and Bestmann-Ohira reaction. This allows for the introduction of electron donating and releasing substituents with different ligation patterns.
View Article and Find Full Text PDFJ Org Chem
July 2021
School of Chemical Sciences, National Institute of Science Education and Research (NISER), HBNI, Bhubaneswar, Jatani, Odisha 752050, India.
The ruthenium(II)-catalyzed regioselective annulation of -(7-azaindole)amides with 1,3-diynes has been demonstrated. Bioactive -amino-7-azaindole has been used as a new bidentate directing group to furnish an array of 3-alkynylated isoquinolones. Furthermore, the developed protocol works efficiently for both aryl- and heteroaryl-substituted amides producing a range of pharmacologically useful 7-azaindole-based isoquinolones with a wide range of functionality.
View Article and Find Full Text PDFChem Commun (Camb)
December 2014
Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700032, India.
An efficient cross-coupling of alkynes with alkynyl and alkenyl halides catalysed by a Ni-Cu system without any ligand has been achieved. The reaction is suggested to proceed by Ni(0) catalysis assisted by Cu(I). A series of functionalised diaryl, aryl-alkyl, aryl-heteroaryl, diheteroaryl 1,3-di-ynes and en-ynes are obtained in high yields.
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