| Synthesis and photochromic properties of molecules containing [e]-annelated dihydropyrenes. Two and three way pi-switches based on the dimethyldihydropyrene-metacyclophanediene valence isomerization. | |
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MedLine Citation:
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PMID: 12617665 Owner: NLM Status: PubMed-not-MEDLINE |
Abstract/OtherAbstract:
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The syntheses of several new simple negative, a simple positive, and multiple negative photochromes containing the dihydropyrene-cyclophanediene photochromic system are described. The photo-openings of the negative photochromes, the [e]-annelated benzo (7), naphtho (9), anthro (11), furano (19), and triphenyleno (15) derivatives of the parent 2,7-di-tert-butyl-trans-10b,10c-dimethyl-dihydropyrene (5), as well as its 4,5-dibromo derivative (13), are described to give the corresponding cyclophanedienes, as well as their photoclosures and thermal closures back to the dihydropyrenes. These are compared to the results obtained for the positive photochrome dibenzo[e,l]dihydropyrene (21) and to the bis(dihydropyreno)chrysene (44) and the (dihydropyrenobenzo)(benzo)metacyclophanediene (47) photochromes, which have more than one photochromic switch present and thus have more than a simple "on-off" state. Thermodynamic data are obtained for the thermal closing reactions. The anthrodihydropyrene (12) has the fastest thermal closing (tau(1/2) = 20 min), while the furanodihydropyrene (19') has the slowest (tau(1/2) = 63 h) at 46 degrees C. An electrochemical readout of the state of the switch is demonstrated for the benzodihydropyrene (7). |
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Authors:
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Reginald H Mitchell; Timothy R Ward; Yongsheng Chen; Yunxia Wang; S Ananda Weerawarna; Peter W Dibble; Michael J Marsella; Adah Almutairi; Zhi-Qiang Wang |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Journal of the American Chemical Society Volume: 125 ISSN: 0002-7863 ISO Abbreviation: J. Am. Chem. Soc. Publication Date: 2003 Mar |
Date Detail:
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Created Date: 2003-03-05 Completed Date: 2004-04-19 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: 2974-88 Citation Subset: - |
Affiliation:
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Department of Chemistry, University of Victoria, P.O. Box 3065, Victoria, British Columbia, Canada V8W 3V6. regmitch@uvic.ca |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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