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An Iodine‐Vapor‐Induced Cyclization in a Crystalline Molecular Flask

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. Th...

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Autores principales: Knichal, Jane V., Shepherd, Helena J., Wilson, Chick C., Raithby, Paul R., Gee, William J., Burrows, Andrew D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5071776/
https://www.ncbi.nlm.nih.gov/pubmed/27060377
http://dx.doi.org/10.1002/anie.201601525
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author Knichal, Jane V.
Shepherd, Helena J.
Wilson, Chick C.
Raithby, Paul R.
Gee, William J.
Burrows, Andrew D.
author_facet Knichal, Jane V.
Shepherd, Helena J.
Wilson, Chick C.
Raithby, Paul R.
Gee, William J.
Burrows, Andrew D.
author_sort Knichal, Jane V.
collection PubMed
description 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 CHCl(3)⋅H(2)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).
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spelling pubmed-50717762016-11-02 An Iodine‐Vapor‐Induced Cyclization in a Crystalline Molecular Flask Knichal, Jane V. Shepherd, Helena J. Wilson, Chick C. Raithby, Paul R. Gee, William J. Burrows, Andrew D. Angew Chem Int Ed Engl Communications 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 CHCl(3)⋅H(2)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). John Wiley and Sons Inc. 2016-04-06 2016-05-10 /pmc/articles/PMC5071776/ /pubmed/27060377 http://dx.doi.org/10.1002/anie.201601525 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution (http://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Knichal, Jane V.
Shepherd, Helena J.
Wilson, Chick C.
Raithby, Paul R.
Gee, William J.
Burrows, Andrew D.
An Iodine‐Vapor‐Induced Cyclization in a Crystalline Molecular Flask
title An Iodine‐Vapor‐Induced Cyclization in a Crystalline Molecular Flask
title_full An Iodine‐Vapor‐Induced Cyclization in a Crystalline Molecular Flask
title_fullStr An Iodine‐Vapor‐Induced Cyclization in a Crystalline Molecular Flask
title_full_unstemmed An Iodine‐Vapor‐Induced Cyclization in a Crystalline Molecular Flask
title_short An Iodine‐Vapor‐Induced Cyclization in a Crystalline Molecular Flask
title_sort iodine‐vapor‐induced cyclization in a crystalline molecular flask
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5071776/
https://www.ncbi.nlm.nih.gov/pubmed/27060377
http://dx.doi.org/10.1002/anie.201601525
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