Insights into the mechanism of the photoinduced Wolff rearrangement of diazonaphthquinone

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dc.contributor.author Li, Quansong
dc.date.issued 2010-07-05
dc.identifier.citation Li, Q. (2010). Insights into the mechanism of the photoinduced Wolff rearrangement of diazonaphthquinone. A 'IX Girona Seminar'. Girona: Universitat. [Consulta 3 setembre 2010]. Disponible a: http://hdl.handle.net/10256.1/1678
dc.identifier.uri http://hdl.handle.net/10256.1/1678
dc.description.abstract Diazonaphthoquinone (DNQ) undergoes the light-induced Wolff rearrangement (WR), which is widely applied in the fabrication of photoresists. Based on the vertical excitation spectrum, the WR mechanism of DNQ has been determined by calculating the reaction paths on the ground and excited state potential energy surface at the CASPT2//CASSCF level. The minimum energy paths (MEPs) start from the Franck-Condon structure on the two lowest energy states of ππ* and ππ*NN character. Both paths lead without a barrier to a conical intersection seam between the ground state (S0) and first excited state (S1). The S1/S0 intersection seam is energetically accessible in experiments (with UV of 400 nm or between 300 and 350 nm) and from this seam different species can be formed: the final ketene product of the rearrangement, a carbene intermediate, a diazirine side product, and the reactant DNQ. According to our calculations, the photo-induced WR of DNQ may occur in a nonsynchronous concerted way or via a carbene intermediate. The comprehensive WR mechanism agrees well with previous experimental observations and may have important implications in organic synthesis and photoresists fabrication
dc.format.mimetype audio/mpeg
dc.format.mimetype video/H263
dc.language.iso eng
dc.publisher Universitat de Girona. Departament de Química
dc.publisher Universitat de Girona. Institut de Química Computacional
dc.relation.ispartofseries IX Girona Seminar
dc.rights Aquest document està subjecte a una llicència Creative Commons: Reconeixement - No comercial - Compartir igual (by-nc-sa)
dc.rights.uri http://creativecommons.org/licenses/by-nc-sa/3.0/es/deed.ca
dc.subject Química quàntica -- Congressos
dc.subject Quantum chemistry -- Congresses
dc.title Insights into the mechanism of the photoinduced Wolff rearrangement of diazonaphthquinone
dc.type info:eu-repo/semantics/lecture


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