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[2.2]Paracyclophane as a Target of the Organic Solid State: Emergent Properties via Supramolecular Construction
Author(s) -
Elacqua Elizabeth,
Friščić Tomislav,
MacGillivray Leonard R.
Publication year - 2012
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.201100089
Subject(s) - chemistry , supramolecular chemistry , solid state , intermolecular force , cycloaddition , molecule , yield (engineering) , template , hydrogen bond , block (permutation group theory) , organic molecules , small molecule , computational chemistry , combinatorial chemistry , nanotechnology , organic chemistry , thermodynamics , catalysis , biochemistry , physics , materials science , geometry , mathematics
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).