Paracyclophane as a target of the organic solid state: Emergent properties via supramolecular construction

Elizabeth Elacqua, Tomislav Friščić, Leonard R. MacGillivray

Research output: Contribution to journalReview articlepeer-review

22 Scopus citations

Abstract

In this account, we review the synthesis of [2.2]paracyclophanes in the organic solid state. Reactions in crystalline solids provide a means to obtain molecules with high degrees of stereocontrol that can also be unattainable in solution. We show that [2.2]paracyclophanes form in the solid state stereospecifically and in quantitative yield via intermolecular [2+2] double photodimerization reactions. The double cycloaddition that affords a paracyclophane in the solid state does not readily occur in solution. Small molecules in the form of hydrogen-bond-donor templates can provide access to [2.2]paracyclophanes in a solid by design. A [2.2]paracyclophane obtained using a hydrogen-bond template is shown to exhibit attractive optical properties and has been employed as a building block of a metal-organic framework (MOF).

Original languageEnglish (US)
Pages (from-to)53-59
Number of pages7
JournalIsrael Journal of Chemistry
Volume52
Issue number1-2
DOIs
StatePublished - Feb 1 2012

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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