Flow-Assisted Synthesis of [10]Cycloparaphenylene through Serial Microreactions under Mild Conditions
- Authors
- 김희진
- Issue Date
- 1월-2016
- Publisher
- WILEY-V C H VERLAG GMBH
- Citation
- ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.55, no.4, pp.1422 - 1426
- Indexed
- SCIE
SCOPUS
- Journal Title
- ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Volume
- 55
- Number
- 4
- Start Page
- 1422
- End Page
- 1426
- URI
- https://scholar.korea.ac.kr/handle/2021.sw.korea/139893
- DOI
- 10.1002/anie.201509748
- ISSN
- 1433-7851
- Abstract
- Cycloparaphenylene (CPP) has been recognized as an attractive template for the bottom-up synthesis of carbon nanotubes with uniform diameter, and is important for the chemistry of graphitic as well as ring-shaped macromolecules. However, the reported routes from halogenated benzenes have suffered from low yields even under time-and labor-consuming multistep conditions. Herein we report a flow-assisted synthesis of [10]CPP in four steps under mild conditions. For the synthesis, a selective nucleophilic addition of the unprotected diketone without the double-added byproduct was achieved within 3 s in high yield. Subsequently, the obtained compound was reacted with dilithiated benzene at 25 degrees C to form a U-shaped precursor for CPP in a separate microreactor, which was finally dimerized and aromatized to obtain [10]CPP by a two-step in-flask reaction. Precise control of time and flow facilitated by the flow-assisted system enabled the development of an efficient synthetic route for [10]CPP.
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