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Issue 8, 2011
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Steady state and transient kinetics in crystalline solids: the photochemistry of nanocrystalline 1,1,3-triphenyl-3-hydroxy-2-indanone

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Abstract

Electronic excitation of crystalline 1,3,3-triphenyl-1-hydroxy-2-indanone results in the exclusive formation of hydroxy-benzocyclobutane while irradiation in solution leads to formation of the isomeric photoenols, which subsequently tautomerize. Using nanocrystals suspended in water we were able to use transmission pump–probe methods to detect the reactive intermediates involved in the solid state. Transients assigned to the 1,4-biradical (triplet enol) formed by adiabatic photodecarbonylation were detected. It was found that product formation occurs from analogous transients, both in solution and in the solid state. While enols revert to ketones in time scales that range from a few hundred nanoseconds to tens of microseconds, benzocyclobutanol remains kinetically trapped in the crystal lattice, but undergoes a thermal ring opening when dissolved.

Graphical abstract: Steady state and transient kinetics in crystalline solids: the photochemistry of nanocrystalline 1,1,3-triphenyl-3-hydroxy-2-indanone

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Article information


Submitted
24 Mar 2011
Accepted
21 Apr 2011
First published
19 May 2011

Chem. Sci., 2011,2, 1497-1501
Article type
Edge Article

Steady state and transient kinetics in crystalline solids: the photochemistry of nanocrystalline 1,1,3-triphenyl-3-hydroxy-2-indanone

G. Kuzmanich, J. Xue, J. Netto-Ferreira, J. C. Scaiano, M. Platz and M. A. Garcia-Garibay, Chem. Sci., 2011, 2, 1497 DOI: 10.1039/C1SC00184A

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