para-Bridged Symmetrical Pillar[5]arenes: Their Lewis Acid Catalyzed Synthesis and Host–Guest Property

Condensation of 1,4-dimethoxybenzene (DMB) with paraformaldehyde in the presence of BF3·O(C2H5)2 gave novel para-bridged pentacyclic pillar DMB (DMpillar[5]arene). Moreover, para-bridged pentacyclic hydroquinone (pillar[5]arene) was prepared. Pillar[5]arene formed 1:1 host–guest complexes with dialk...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 130; no. 15; pp. 5022 - 5023
Main Authors Ogoshi, Tomoki, Kanai, Suguru, Fujinami, Shuhei, Yamagishi, Tada-aki, Nakamoto, Yoshiaki
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.04.2008
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
COMPLEXATION
CYCLODEXTRIN
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Summary:Condensation of 1,4-dimethoxybenzene (DMB) with paraformaldehyde in the presence of BF3·O(C2H5)2 gave novel para-bridged pentacyclic pillar DMB (DMpillar[5]arene). Moreover, para-bridged pentacyclic hydroquinone (pillar[5]arene) was prepared. Pillar[5]arene formed 1:1 host–guest complexes with dialkyl viologen and alkyl pyridinium derivatives. However, pillar[5]arene did not form complexes with the diadamantyl viologen derivative since a bulky adamantyl group was unable to thread the cavity of pillar[5]arene.
Bibliography:Experimental section, 1H, 13C, and variable-temperature 1H NMR spectra of DMpillar[5]arene and pillar[5]arene, X-ray crystallographic data in CIF format, ORTEP drawing of DMpillar[5]arene, structures of DMpillar[5]arene and calix[6]arene, Job plots, MALDI-TOF mass spectrum of the host–guest complex of C8BpyC8 with pillar[5]arene, and 1H NMR spectra of C8BpyC8 with p-tert-butylcalix[6]arene and AdBpyAd with pillar[5]arene, determination of the association constants from fluorescence measurements. This material is available free of charge via the Internet at http://pubs.acs.org.
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja711260m