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

Yuki Fujii | Zendy; Y Suwa | Zendy; Yuki Wada | Zendy; Tsunayoshi Takehara | Zendy; Takeyuki Suzuki | Zendy; Yusuke Kawashima | Zendy; Norihito Kawashita | Zendy; Tatsuya Takagi | Zendy; Hiromichi Fujioka | Zendy; Mitsuhiro Arisawa | Zendy

Open Access

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

Author(s) -

Yuki Fujii,

Y Suwa,

Yuki Wada,

Tsunayoshi Takehara,

Takeyuki Suzuki,

Yusuke Kawashima,

Norihito Kawashita,

Tatsuya Takagi,

Hiromichi Fujioka,

Mitsuhiro Arisawa

Publication year - 2019

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.9b00315

Subject(s) - quinoline , chemistry , absorption (acoustics) , cycloaddition , ruthenium , photochemistry , ring (chemistry) , reactivity (psychology) , metathesis , absorption spectroscopy , catalysis , organic chemistry , materials science , medicine , alternative medicine , polymer , physics , pathology , quantum mechanics , composite material , polymerization

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.

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