Self‐assembly of daisy chain oligomers from heteroditopic molecules containing secondary ammonium ion and crown ether moieties |
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| Authors: | Harry W. Gibson Nori Yamaguchi Zhenbin Niu Jason W. Jones Carla Slebodnick Arnold L. Rheingold Lev N. Zakharov |
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| Affiliation: | 1. Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, Virginia 24061;2. Department of Chemistry, University of Delaware, Newark, Delaware 19716 |
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| Abstract: | MALDI‐TOF MS of the heteroditopic compound 2 ‐(benzylammoniomethyl)dibenzo‐24‐crown‐8 hexafluorophosphate ( 4 ) revealed oligomeric “daisy chain” species up to the hexamer. Similar results were obtained for 2‐(6′‐hydroxyhexylammoniomethyl)dibenzo‐24‐crown‐8 hexafluorophosphate ( 8 ). The complexations of two substituted dibenzylammonium salts, 2,2′‐dimethyldibenzylammonium hexaflurophosphate ( 9a ) and 2,2′,5‐trimethoxydibenzylammonium hexafluorophosphate ( 9b ), with dibenzo‐24‐crown‐8 were examined as models for slippage systems; association constants are reported for these systems. A crystal structure is reported for the new dimethylbenzylammonoium pseudorotaxane. The trimethoxy analog is shown to be capable of slippage formation of a rotaxane, albeit in low yield. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 975–985, 2010 |
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| Keywords: | crown ether crystal structure host– guest systems macrocycles mass spectrometry pseudorotaxane self‐organization supramolecular polymer |
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