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Improving Fatigue Resistance of Dihydropyrene by Encapsulation within a Coordination Cage

Canton, Martina (author)
Weizmann Institute of Science,Universita di Bologna,University of Bologna
Grommet, Angela Beth, 1991 (author)
Weizmann Institute of Science
Pesce, Luca (author)
Scuola Universitaria Professionale della Svizzera Italiana (SUPSI),University of Applied Sciences and Arts of Italian Switzerland (SUPSI)
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Gemen, Julius (author)
Weizmann Institute of Science
Li, Shiming, 1947 (author)
Chalmers tekniska högskola,Chalmers University of Technology
Diskin-Posner, Yael (author)
Weizmann Institute of Science
Credi, Alberto (author)
Universita di Bologna,University of Bologna
Pavan, Giovanni M. (author)
Politecnico di Torino,Polytechnic University of Turin,Scuola Universitaria Professionale della Svizzera Italiana (SUPSI),University of Applied Sciences and Arts of Italian Switzerland (SUPSI)
Andreasson, Joakim, 1973 (author)
Chalmers tekniska högskola,Chalmers University of Technology
Klajn, Rafal (author)
Weizmann Institute of Science
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 (creator_code:org_t)
2020-08-14
2020
English.
In: Journal of the American Chemical Society. - : American Chemical Society (ACS). - 1520-5126 .- 0002-7863. ; 142:34, s. 14557-14565
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  • Journal article (peer-reviewed)
Abstract Subject headings
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  • Photochromic molecules undergo reversible isomerization upon irradiation with light at different wavelengths, a process that can alter their physical and chemical properties. For instance, dihydropyrene (DHP) is a deep-colored compound that isomerizes to light-brown cyclophanediene (CPD) upon irradiation with visible light. CPD can then isomerize back to DHP upon irradiation with UV light or thermally in the dark. Conversion between DHP and CPD is thought to proceed via a biradical intermediate; bimolecular events involving this unstable intermediate thus result in rapid decomposition and poor cycling performance. Here, we show that the reversible isomerization of DHP can be stabilized upon confinement within a (PdIIL4)-L-6 coordination cage. By protecting this reactive intermediate using the cage, each isomerization reaction proceeds to higher yield, which significantly decreases the fatigue experienced by the system upon repeated photocycling. Although molecular confinement is known to help stabilize reactive species, this effect is not typically employed to protect reactive intermediates and thus improve reaction yields. We envisage that performing reactions under confinement will not only improve the cyclic performance of photochromic molecules, but may also increase the amount of product obtainable from traditionally low-yielding organic reactions.

Subject headings

NATURVETENSKAP  -- Kemi -- Polymerkemi (hsv//swe)
NATURAL SCIENCES  -- Chemical Sciences -- Polymer Chemistry (hsv//eng)
NATURVETENSKAP  -- Biologi -- Biokemi och molekylärbiologi (hsv//swe)
NATURAL SCIENCES  -- Biological Sciences -- Biochemistry and Molecular Biology (hsv//eng)
NATURVETENSKAP  -- Fysik -- Atom- och molekylfysik och optik (hsv//swe)
NATURAL SCIENCES  -- Physical Sciences -- Atom and Molecular Physics and Optics (hsv//eng)

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