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Polyacetylenes with (hetero)aryl-, styryl-, and amino-phenothiazinyl sidechains: synthesis and photophysics.

ABSTRACT: A novel generation of 7-aryl phenothiazinyl substituted polyacetylenes is readily accessible via 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 (Φ_f = 0.06) and display moderate Stokes shifts and positive emission solvatochromism.

SUBMITTER: Pisetsky W

PROVIDER: S-EPMC10985593 | biostudies-literature | 2024 Mar

REPOSITORIES: biostudies-literature

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Polyacetylenes with (hetero)aryl-, styryl-, and amino-phenothiazinyl sidechains: synthesis and photophysics.

Pisetsky Wladislaw W Müller Thomas J J TJJ

RSC advances 20240301 15

A novel generation of 7-aryl phenothiazinyl substituted polyacetylenes is readily accessible <i>via</i> 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 distr ...[more]

PMID: 38567317

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