| A self-locking molecule operative with a photoresponsive key. | |
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MedLine Citation:
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PMID: 16939284 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Rotary host 1, composed of a ferrocene unit as a rotary module, is conformationally locked internally in apolar solvents such as benzene by a double intramolecular Zn-N coordination between the zinc porphyrin and aniline units, attached to each cyclopentadienyl (Cp) ring. Upon addition of the cis form of 1,2-bispyridylethylene (cis-2) to (+)-1 ([cis-2]/[(+)-1] = 5.0), an enantiomer of 1, the intramolecular Zn-N coordination bonds in (+)-1 are readily cleaved to form an externally locked, cyclodimeric one-to-one complex (+)-1 subset cis-2, accompanying a rotation of the ferrocene module, as visualized by CD spectroscopy. In contrast, use of trans-2, in place of cis-2, under otherwise identical conditions to the above, did not result in releasing the internal double lock of (+)-1. Such a large difference between the isomers of 2 in the affinity toward host 1, along with their capabilities of photochemical interconversion, allowed for the demonstration of a reversible self-locking operation of 1. Namely, the externally locked state of 1, as in the form of 1 supersetcis-2, spontaneously retrieves the internally locked state, after the release of 2 from 1 upon cis-to-trans photochemical isomerization of ligating 2, while the backward photochemical isomerization of 2 in the presence of 1 results in switching of 1 to its externally locked state. |
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Authors:
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Takahiro Muraoka; Kazushi Kinbara; Takuzo Aida |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Journal of the American Chemical Society Volume: 128 ISSN: 0002-7863 ISO Abbreviation: J. Am. Chem. Soc. Publication Date: 2006 Sep |
Date Detail:
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Created Date: 2006-08-30 Completed Date: 2007-08-08 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 7503056 Medline TA: J Am Chem Soc Country: United States |
Other Details:
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Languages: eng Pagination: 11600-5 Citation Subset: IM |
Affiliation:
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Department of Chemistry and Biotechnology, School of Engineering, and Center for NanoBio Integration, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656, Japan. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Aniline Compounds
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chemistry Circular Dichroism Cyclopentanes / chemistry Ferrous Compounds / chemical synthesis*, chemistry* Magnetic Resonance Spectroscopy Metalloporphyrins / chemistry Models, Molecular Photochemistry Pyridines / chemistry Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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0/Aniline Compounds; 0/Cyclopentanes; 0/Ferrous Compounds; 0/Metalloporphyrins; 0/Pyridines; 102-54-5/ferrocene; 13939-11-2/zinc hematoporphyrin; 62-53-3/aniline |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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