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°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.
Original language | English |
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Pages (from-to) | 1422-1426 |
Number of pages | 5 |
Journal | Angewandte Chemie - International Edition |
Volume | 55 |
Issue number | 4 |
DOIs | |
Publication status | Published - 2016 Jan 22 |
Externally published | Yes |
Bibliographical note
Funding Information:This work was supported by a National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIP; No. 2008–0061983)
Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Keywords
- cycloparaphenylene
- flow chemistry
- lithiation
- microfluidics
- microreactors
ASJC Scopus subject areas
- Catalysis
- General Chemistry