Flow-Assisted Synthesis of [10]Cycloparaphenylene through Serial Microreactions under Mild Conditions

Heejin Kim, Hyune Jea Lee, Dong Pyo Kim

Research output: Contribution to journalArticle

15 Citations (Scopus)

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 languageEnglish
Pages (from-to)1422-1426
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number4
DOIs
Publication statusPublished - 2016 Jan 22
Externally publishedYes

Keywords

  • cycloparaphenylene
  • flow chemistry
  • lithiation
  • microfluidics
  • microreactors

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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