An Iodine-Vapour-Induced Cyclization in a Crystalline Molecular Flask

Jane Knichal, Helena Shepherd, Charles Wilson, Paul Raithby, William Gee, Andrew Burrows

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Abstract

A vapour-induced cyclisation has been demonstrated in the hosted environment of a crystalline molecular flask (CMF), within which 1,8-bis(2-phenylethynyl)naphthalene (bpen), a diarenynyl system primed for cyclisation, has been exposed to iodine vapour to yield the corresponding indeno[2,1-α]phenalene species. The cyclisation process, unique in its vapour-induced, solvent-free nature, has been followed spectroscopically, and found to occur concurrently with the displacement of lattice solvent for molecular iodine in CMF·0.75bpen·2.25CHCl3·H2O. The cyclisation occurs under mild conditions and without the need to suspend the crystals in solvent. The ability of CMFs to host purely gas-induced reactions is further highlighted by a subsequent, sequential, oxidation reaction of the cyclised 7-iodo-12-phenylindeno[2,1-α]phenalene (ipp) with molecular oxygen derived from air, yielding 12-hydroxy-7-iodo-2-phenylindeno[2,1-α]phenalen-1(12H)-one (hipp).
Original languageEnglish
Pages (from-to)5943-5946
Number of pages4
JournalAngewandte Chemie-International Edition
Volume55
Issue number20
Early online date6 Apr 2016
DOIs
Publication statusPublished - 3 May 2016

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Cyclization
Iodine
Gases
Air
Oxygen

Keywords

  • Cyclization
  • Host-guest systems
  • Iodine
  • Porous networks
  • X-ray diffraction

Cite this

An Iodine-Vapour-Induced Cyclization in a Crystalline Molecular Flask. / Knichal, Jane; Shepherd, Helena; Wilson, Charles; Raithby, Paul; Gee, William; Burrows, Andrew.

In: Angewandte Chemie-International Edition, Vol. 55, No. 20, 03.05.2016, p. 5943-5946.

Research output: Contribution to journalArticle

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AB - A vapour-induced cyclisation has been demonstrated in the hosted environment of a crystalline molecular flask (CMF), within which 1,8-bis(2-phenylethynyl)naphthalene (bpen), a diarenynyl system primed for cyclisation, has been exposed to iodine vapour to yield the corresponding indeno[2,1-α]phenalene species. The cyclisation process, unique in its vapour-induced, solvent-free nature, has been followed spectroscopically, and found to occur concurrently with the displacement of lattice solvent for molecular iodine in CMF·0.75bpen·2.25CHCl3·H2O. The cyclisation occurs under mild conditions and without the need to suspend the crystals in solvent. The ability of CMFs to host purely gas-induced reactions is further highlighted by a subsequent, sequential, oxidation reaction of the cyclised 7-iodo-12-phenylindeno[2,1-α]phenalene (ipp) with molecular oxygen derived from air, yielding 12-hydroxy-7-iodo-2-phenylindeno[2,1-α]phenalen-1(12H)-one (hipp).

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