Wolff Rearrangement of 2-diazo-1(2H)-naphthalenone induced by nonresonant two-photon absorption of NIR radiation |
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Authors: | Urdabayev Nurtay K Popik Vladimir V |
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Institution: | Center for Photochemical Sciences, Bowling Green State University, Bowling Green, Ohio 43402, USA. |
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Abstract: | The irradiation of 2-diazo-1(2H)-naphthalenone (1), the common component of positive photoresists, with 800 nm pulses of ultrafast laser results in Wolff rearrangement via nonresonant two-photon absorbance of light. The 10% conversion of starting material resulting in the formation of methyl 1H-indene-3-carboxylate (2) was achieved after 11 min of irradiation of the methanol solution of 1 with an unfocused beam of a Ti:Sapphire laser operating at 1 kHz. The two-photon cross-section of the diazonaphthoquinone 1 at 800 nm was calculated to be sigma = 2.2 x 10-51 cm4 s photon-1 (0.2 GM). |
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