An Adaptable Water-Soluble Molecular Boat for Selective Separation of Phenanthrene from Isomeric Anthracene

J Am Chem Soc. 2022 Apr 27;144(16):7504-7513. doi: 10.1021/jacs.2c02540. Epub 2022 Apr 18.

Abstract

Anthracene crude oil is a common source of phenanthrene for its industrial use. The isolation of phenanthrene from this source is a challenging task due to very similar physical properties to its isomer anthracene. We report here a water-soluble Pd(II) molecular boat (MB1) with unusual structural topology that was obtained by assembling a flexible tetrapyridyl donor (L) with a cis-Pd(II) acceptor. The flexible backbone of the boat enabled it to breathe in the presence of a guest optimizing the fit within the cavity. The boat binds phenanthrene more strongly than anthracene, which enabled separation of phenanthrene with an >98% purity from an equimolar mixture of the two isomers using MB1 as an extracting agent. MB1 represents a unique example of a coordination receptor suitable for selective aqueous extraction of phenanthrene from anthracene with reusability of several cycles.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anthracenes / chemistry
  • Phenanthrenes* / chemistry
  • Ships*
  • Water / chemistry

Substances

  • Anthracenes
  • Phenanthrenes
  • Water