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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
[Image: see text] 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...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2019
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648314/ https://www.ncbi.nlm.nih.gov/pubmed/31459684 http://dx.doi.org/10.1021/acsomega.9b00315 |
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author | Fujii, Yuki Suwa, Yukinori Wada, Yuki Takehara, Tsunayoshi Suzuki, Takeyuki Kawashima, Yusuke Kawashita, Norihito Takagi, Tatsuya Fujioka, Hiromichi Arisawa, Mitsuhiro |
author_facet | Fujii, Yuki Suwa, Yukinori Wada, Yuki Takehara, Tsunayoshi Suzuki, Takeyuki Kawashima, Yusuke Kawashita, Norihito Takagi, Tatsuya Fujioka, Hiromichi Arisawa, Mitsuhiro |
author_sort | Fujii, Yuki |
collection | PubMed |
description | [Image: see text] 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. |
format | Online Article Text |
id | pubmed-6648314 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-66483142019-08-27 Metal-Free Nitrogen-Containing Polyheterocyclic Near-Infrared (NIR) Absorption Dyes: Synthesis, Absorption Properties, and Theoretical Calculation of Substituted 5-Methylisoindolo[2,1-a]quinolines Fujii, Yuki Suwa, Yukinori Wada, Yuki Takehara, Tsunayoshi Suzuki, Takeyuki Kawashima, Yusuke Kawashita, Norihito Takagi, Tatsuya Fujioka, Hiromichi Arisawa, Mitsuhiro ACS Omega [Image: see text] 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. American Chemical Society 2019-03-08 /pmc/articles/PMC6648314/ /pubmed/31459684 http://dx.doi.org/10.1021/acsomega.9b00315 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
spellingShingle | Fujii, Yuki Suwa, Yukinori Wada, Yuki Takehara, Tsunayoshi Suzuki, Takeyuki Kawashima, Yusuke Kawashita, Norihito Takagi, Tatsuya Fujioka, Hiromichi Arisawa, Mitsuhiro Metal-Free Nitrogen-Containing Polyheterocyclic Near-Infrared (NIR) Absorption Dyes: Synthesis, Absorption Properties, and Theoretical Calculation of Substituted 5-Methylisoindolo[2,1-a]quinolines |
title | Metal-Free Nitrogen-Containing Polyheterocyclic Near-Infrared
(NIR) Absorption Dyes: Synthesis, Absorption Properties, and Theoretical
Calculation of Substituted 5-Methylisoindolo[2,1-a]quinolines |
title_full | Metal-Free Nitrogen-Containing Polyheterocyclic Near-Infrared
(NIR) Absorption Dyes: Synthesis, Absorption Properties, and Theoretical
Calculation of Substituted 5-Methylisoindolo[2,1-a]quinolines |
title_fullStr | Metal-Free Nitrogen-Containing Polyheterocyclic Near-Infrared
(NIR) Absorption Dyes: Synthesis, Absorption Properties, and Theoretical
Calculation of Substituted 5-Methylisoindolo[2,1-a]quinolines |
title_full_unstemmed | Metal-Free Nitrogen-Containing Polyheterocyclic Near-Infrared
(NIR) Absorption Dyes: Synthesis, Absorption Properties, and Theoretical
Calculation of Substituted 5-Methylisoindolo[2,1-a]quinolines |
title_short | Metal-Free Nitrogen-Containing Polyheterocyclic Near-Infrared
(NIR) Absorption Dyes: Synthesis, Absorption Properties, and Theoretical
Calculation of Substituted 5-Methylisoindolo[2,1-a]quinolines |
title_sort | metal-free nitrogen-containing polyheterocyclic near-infrared
(nir) absorption dyes: synthesis, absorption properties, and theoretical
calculation of substituted 5-methylisoindolo[2,1-a]quinolines |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648314/ https://www.ncbi.nlm.nih.gov/pubmed/31459684 http://dx.doi.org/10.1021/acsomega.9b00315 |
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