Chiral Discrimination in Photochromic Helicenes

A photoresponsive dithienylethene derivative bearing chiral pinene-based arms underwent a stereoselective photoinduced cyclization reaction to produce greater than 98% of a single diastereomer. The magnitude of the optical rotation changed as much as Δ[α]373 = 8698° upon alternate irradiation with 4...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 127; no. 20; pp. 7272 - 7273
Main Authors Wigglesworth, Tony J, Sud, David, Norsten, Tyler B, Lekhi, Vikram S, Branda, Neil R
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 25.05.2005
Amer Chemical Soc
Subjects
Atomic and molecular physics
Chemistry
Chemistry, Multidisciplinary
Exact sciences and technology
Molecular properties and interactions with photons
Optical activity and dichroism; magnetooptical and electrooptical spectra
Optical activity, optical rotation; circular dichroism
Physical Sciences
Physics
Science & Technology
OPTICAL-PROPERTIES
CRYSTALS
DIARYLETHENE
SUPRAMOLECULAR CHIRALITY
Aromatics
Sulfur heterocycle
Photochromism
Organic solvents
Benzene
Optical activity
Helicene
Experimental study
Organic compounds
Circular dichroism
Ultraviolet visible spectrometry
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Summary:A photoresponsive dithienylethene derivative bearing chiral pinene-based arms underwent a stereoselective photoinduced cyclization reaction to produce greater than 98% of a single diastereomer. The magnitude of the optical rotation changed as much as Δ[α]373 = 8698° upon alternate irradiation with 400 nm and greater than 434 nm light.
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ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja050190j