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Metal-Free Nitrogen-Containing Polyheterocyclic Near-Infrared (NIR) Absorption Dyes: Synthesis, Absorption Properties, and Theoretical Calculation of Substituted 5-Methylisoindolo[2,1-a]quinolines.

ABSTRACT: We have synthesized and theoretically calculated 5-methylisoindolo[2,1-a]quinoline derivatives as novel near-infrared absorption dyes via a ruthenium-catalyzed one-pot metathesis/oxidation/1,3-dipolar cycloaddition protocol. The reactivity in 1,3-dipolar cycloaddition was governed by the electronic effect of aromatic ring substituents. Substrates with an electron-withdrawing group on the aromatic ring afforded higher yields. The maximal absorption wavelength of 3,5-dimethyl-11-phenylisoindolo[2,1-a]quinoline-7,10-dione and 11-(4-methoxyphenyl)-5-methylisoindolo[2,1-a]quinoline-7,10-dione in MeOH increased to 736 and 737 nm, although that of 3a was 727 nm.

SUBMITTER: Fujii Y

PROVIDER: S-EPMC6648314 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

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Metal-Free Nitrogen-Containing Polyheterocyclic Near-Infrared (NIR) Absorption Dyes: Synthesis, Absorption Properties, and Theoretical Calculation of Substituted 5-Methylisoindolo[2,1-<i>a</i>]quinolines.

Fujii Yuki Y Suwa Yukinori Y Wada Yuki Y Takehara Tsunayoshi T Suzuki Takeyuki T Kawashima Yusuke Y Kawashita Norihito N Takagi Tatsuya T Fujioka Hiromichi H Arisawa Mitsuhiro M

ACS omega 20190308 3

We have synthesized and theoretically calculated 5-methylisoindolo[2,1-<i>a</i>]quinoline derivatives as novel near-infrared absorption dyes via a ruthenium-catalyzed one-pot metathesis/oxidation/1,3-dipolar cycloaddition protocol. The reactivity in 1,3-dipolar cycloaddition was governed by the electronic effect of aromatic ring substituents. Substrates with an electron-withdrawing group on the aromatic ring afforded higher yields. The maximal absorption wavelength of 3,5-dimethyl-11-phenylisoin ...[more]

PMID: 31459684

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