Improving Fatigue Resistance of Dihydropyrene by Encapsulation within a Coordination Cage

Canton, MartinaWeizmann Institute of Science,Universita di Bologna,University of Bologna (författare)

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.

Grommet, Angela Beth,1991Weizmann Institute of Science(Swepub:cth)grommet (författare)
Pesce, LucaScuola Universitaria Professionale della Svizzera Italiana (SUPSI),University of Applied Sciences and Arts of Italian Switzerland (SUPSI) (författare)
Gemen, JuliusWeizmann Institute of Science (författare)
Li, Shiming,1947Chalmers tekniska högskola,Chalmers University of Technology(Swepub:cth)shiming (författare)
Diskin-Posner, YaelWeizmann Institute of Science (författare)
Credi, AlbertoUniversita di Bologna,University of Bologna (författare)
Pavan, Giovanni M.Politecnico di Torino,Polytechnic University of Turin,Scuola Universitaria Professionale della Svizzera Italiana (SUPSI),University of Applied Sciences and Arts of Italian Switzerland (SUPSI) (författare)
Andreasson, Joakim,1973Chalmers tekniska högskola,Chalmers University of Technology(Swepub:cth)a-son (författare)
Klajn, RafalWeizmann Institute of Science (författare)
Weizmann Institute of ScienceUniversita di Bologna (creator_code:org_t)

Ingår i:Journal of the American Chemical Society: American Chemical Society (ACS)142:34, s. 14557-145651520-51260002-7863

Av författaren/redakt...: Canton, Martina; Grommet, Angela ...; Pesce, Luca; Gemen, Julius; Li, Shiming, 194 ...; Diskin-Posner, Y ...; visa fler...; Credi, Alberto; Pavan, Giovanni ...; Andreasson, Joak ...; Klajn, Rafal; visa färre...

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