Synthesis of azafluoranthenes by iridium-catalyzed [2+2+2] cycloaddition and evaluation of their fluorescence properties

被引：4

作者：

Sawano, Takahiro ^{[1
]}

Takamura, Kaho ^{[1
]}

Yoshikawa, Tomoka ^{[1
]}

Murata, Kayo ^{[1
]}

Koga, Marina ^{[1
]}

Yamada, Risa ^{[1
]}

Saito, Takahide ^{[1
]}

Tabata, Kazumasa ^{[1
]}

Ishii, Yugo ^{[1
]}

Kashihara, Wataru ^{[1
]}

Nishihara, Tatsuya ^{[1
]}

Tanabe, Kazuhito ^{[1
]}

Suzuki, Tadashi ^{[1
]}

Takeuchi, Ryo ^{[1
]}

机构：

[1] Aoyama Gakuin Univ, Dept Chem & Biol Sci, 5-10-1 Fuchinobe, Chuo Ku, Sagamihara, Kanagawa 2525258, Japan

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2023年 / 21卷 / 02期

关键词：

ANNULATED ANALOGS; A-D; ALKALOIDS; DERIVATIVES; ALPHA; OMEGA-DIYNES; INDUCTION; NITRILE; SPECTRA; DIYNES;

D O I：

10.1039/d2ob01921c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a method for the synthesis of azafluoranthenes under neutral reaction conditions in a highly atom-economical manner by the iridium-catalyzed [2 + 2 + 2] cycloaddition of 1,8-dialkynylnaphthalenes with nitriles. A variety of nitriles react with methyl- or phenyl-substituted 1,8-dialkynylnaphthalenes to give a wide range of azafluoranthenes. Azafluoranthenes bearing an amino group show intense fluorescence at around 500 nm. Comparison of the fluorescence properties of amine-substituted azafluoranthenes with related compounds revealed the importance of the amine moiety for obtaining a high fluorescence quantum yield. The choice of the solvent affected the emission maxima and the fluorescence quantum yield. Azafluoranthenes bearing pyrrolidine exhibited blue-shifted emission bands in a non-polar solvent and gave a fluorescence quantum yield of 0.76 in toluene. A Lippert-Mataga plot and computational studies provide insight into the origin of the fluorescence of azafluoranthenes. Furthermore, cellular experiments using human breast adenocarcinoma cells SK-BR-3 demonstrated the feasibility of using azafluoranthenes as fluorescent probes.

引用

页码：323 / 331

页数：9

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