Preparation of Chromeno[b]quinoline Derivatives and Their Application for Lipid Droplets Markers

Functional dyes with a chromeno­[b]­quinoline skeleton (3a–d) were synthesized by one-step cyclization between coumarin derivatives and aromatic amines under the promotion of anhydrous aluminum chloride in 41.2–45.8% yields. Their maximum absorption and emission wavelengths locate at 358–396 and 420...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-08, Vol.87 (15), p.10385-10389
Main Authors: Zhu, Ming-Sen, Zhang, Xiao-Qing, Wang, Ya-Nan, Xu, Yu-Jie, Sun, Ru, Ge, Jian-Feng
Format: Article
Language:English
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Summary:Functional dyes with a chromeno­[b]­quinoline skeleton (3a–d) were synthesized by one-step cyclization between coumarin derivatives and aromatic amines under the promotion of anhydrous aluminum chloride in 41.2–45.8% yields. Their maximum absorption and emission wavelengths locate at 358–396 and 420–603 nm with large Stokes shifts (168–231 nm), and their intramolecular charge transfer has been corroborated by density functional theory calculations. Cell experiments have proved that the probes 3a–c possess the ability to target lipid droplets.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c00667