Molecular Tectonics. Construction of Porous Hydrogen-Bonded Networks from Bisketals of Pentaerythritol

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DOIResolve DOI: http://doi.org/10.1021/jo026267tS0022-3263(02)06267-9
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TypeArticle
Journal titleJournal Of Organic Chemistry
ISSN00223263
Volume68
Issue2
Pages240246; # of pages: 7
Abstract2,4,8,10-Tetraoxaspiro[5,5]undecanes tetrasubstituted at the 3 and 9 positions with groups incorporating diaminotriazines can be used for the construction of extensively hydrogen-bonded networks by the strategy of molecular tectonics. Four such compounds, tectons 1-4, were made by short and efficient syntheses involving bisketalization of pentaerythritol and subsequent reactions. Unlike tectons typically used in previous studies, compounds 1-4 are flexible and chiral, and they orient four sticky diaminotriazine groups in a distorted tetrahedral geometry. Tecton 1 crystallizes from DMF/toluene as an inclusion compound of approximate composition 1?8DMF?xH2O. In the resulting structure, each tecton participates in a total of 16 hydrogen bonds. Eight of these bonds involve four principal neighbors, and the tectons linked in this way define a distorted diamondoid network. Despite 8-fold interpenetration, 60% of the volume of the network is available for including guests. The guests are disordered and occupy parallel helical channels that have cross sections of approximately 11 ? 12 ?2 at the narrowest points. These channels provide access to the interior of the crystals and permit guests to be exchanged quantitatively without loss of crystallinity. It is noteworthy that tecton 1, despite its flexibility, small size, and structural simplicity, is apparently unable to find a periodic three-dimensional structure in which the dictates of hydrogen bonding and close packing are satisfied simultaneously.
Publication date
AffiliationNational Research Council Canada; NRC Steacie Institute for Molecular Sciences
Peer reviewedNo
Identifier10008226
NPARC number12339212
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Record identifier95ba041f-5641-4f92-8cb1-9097665673bd
Record created2009-09-11
Record modified2016-05-09
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