title: An Iodine-Vapor-Induced Cyclization in a Crystalline Molecular Flask.
abstract: A vapor-induced cyclization has been observed in the host environment of a crystalline molecular flask (CMF), within which 1,8-bis(2-phenylethynyl)naphthalene (bpen), a diarenynyl system primed for cyclization, was exposed to iodine vapor to yield the corresponding indeno[2,1-α]phenalene species. The cyclization process, unique in its vapor-induced, solvent-free nature, was followed spectroscopically, and found to occur concurrently with the displacement of lattice solvent for molecular iodine in CMF⋅0.75 bpen⋅2.25 CHCl3 ⋅H2 O. The cyclization occurred 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 the subsequent sequential oxidation reaction of cyclized 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).
authors.affiliation: Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, UK.
authors.forename: Jane V
authors.initials: JV
authors.lastname: Knichal
authors.affiliation: School of Physical Sciences, University of Kent, Canterbury, Kent, CT2 7NH, UK.
authors.forename: Helena J
authors.initials: HJ
authors.lastname: Shepherd
authors.affiliation: Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, UK.
authors.forename: Chick C
authors.initials: CC
authors.lastname: Wilson
authors.affiliation: Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, UK.
authors.forename: Paul R
authors.initials: PR
authors.lastname: Raithby
authors.affiliation: Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, UK.
authors.forename: William J
authors.initials: WJ
authors.lastname: Gee
authors.affiliation: Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, UK. A.D.Burrows@bath.ac.uk.
authors.forename: Andrew D
authors.identifier: 0000-0002-9268-4408
authors.initials: AD
authors.lastname: Burrows
keywords: X-ray diffraction; cyclization; host-guest systems; iodine; porous networks