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Halogen‐Bond‐Templated [2+2] Photodimerization in the Solid State: Directed Synthesis and Rare Self‐Inclusion of a Halogenated Product
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Halogen‐Bond‐Templated [2+2] Photodimerization in the Solid State: Directed Synthesis and Rare Self‐Inclusion of a Halogenated Product

Michael A Sinnwell and Leonard R MacGillivray
Angewandte Chemie (International ed.), Vol.55(10), pp.3477-3480
03/01/2016
DOI: 10.1002/anie.201510912
PMID: 26836572

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Abstract

A ditopic halogen‐bond acceptor organizes a diiodooctafluorostilbene for a [2+2] photodimerization reaction to take place between two stilbene molecules in the solid state. The resultant cyclobutane product is functionalized with halogen atoms and undergoes self‐assembly to form a channel‐type host–guest compound that exhibits a very rare form of self‐inclusion. This way, please: A ditopic halogen‐bond acceptor organizes a halogenated stilbene for a stereoselective [2+2] photodimerization reaction to take place between two stilbenes in the solid state. The resultant halogen‐functionalized cyclobutane product self‐assembles to form a host–guest compound that exhibits a very rare form of self‐inclusion. Atom colors: C=gray; I=purple; N=blue; F=green.
dimerization halocarbon compounds halogen bonding molecular recognition self-assembly

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