Journal article
[2.2]Paracyclophane as a Target of the Organic Solid State: Emergent Properties via Supramolecular Construction
Israel journal of chemistry, Vol.52(1-2), pp.53-59
02/2012
DOI: 10.1002/ijch.201100089
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). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Details
- Title: Subtitle
- [2.2]Paracyclophane as a Target of the Organic Solid State: Emergent Properties via Supramolecular Construction
- Creators
- Elizabeth Elacqua - Department of Chemistry, University of Iowa, Iowa City, IA 52245-1294 (USA) phone:+319 335-3504 fax:+319 335-1270Tomislav Friščić - Department of Chemistry, University of Iowa, Iowa City, IA 52245-1294 (USA) phone:+319 335-3504 fax:+319 335-1270Leonard R MacGillivray - Department of Chemistry, University of Iowa, Iowa City, IA 52245-1294 (USA) phone:+319 335-3504 fax:+319 335-1270
- Resource Type
- Journal article
- Publication Details
- Israel journal of chemistry, Vol.52(1-2), pp.53-59
- Publisher
- WILEY-VCH Verlag
- DOI
- 10.1002/ijch.201100089
- ISSN
- 0021-2148
- eISSN
- 1869-5868
- Number of pages
- 7
- Language
- English
- Date published
- 02/2012
- Academic Unit
- Pharmaceutical Sciences and Experimental Therapeutics; Chemistry
- Record Identifier
- 9984216675402771
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