Laboratory for Molecular Photonics
Department of Chemistry
University of Miami
Goal: The goal of this project was the identification of structural designs for the realization of photochromic compounds with fast switching speeds and good fatigue resistances.
Results: The Laboratory of Molecular Photonics developed a new family of photochromic compounds, based on the photoinduced opening and thermal closing of oxazine rings, with submicrosecond switching speeds and excellent fatigue resistances.
Keywords: Isomerizations Molecular Switches Oxazines Photochromism
"Fast and Stable Photochromic Oxazines": M. Tomasulo, S. Sortino, A. J. P. White, F. M. Raymo, J. Org. Chem., 2005, 70, 8180–8189
"Bichromophoric Photochromes Based on the Opening and Closing of a Single Oxazine Ring": M. Tomasulo, S. Sortino, F. M. Raymo, J. Org. Chem., 2008, 73, 118–126
"Substituent Effects on the Photochromism of Bichromophoric Oxazines": E. Deniz, M. Tomasulo, S. Sortino, F. M. Raymo, J. Phys. Chem. C, 2009, 113, 8491–8497
"Computational Insights on the Isomerization of Photochromic Oxazines": Raymo, F. M. J. Phys. Chem. A, 2012, 116, 11888–11895
"Photochromic Compounds Based on Ring Opening and Closing of a [1,3]Oxazine Compound": F. M. Raymo, M. Tomasulo, U.S. Pat. 7,790,068 B2: September 7, 2010
"Use of Oxazine Compounds for Making Chromogenic Materials": F. M. Raymo, M. Tomasulo, U.S. Pat. Appl. 20100249403: September 30, 2010
"Photochromic Compounds Based on Ring Opening and Closing of a [1,3]Oxazine Compound": F. M. Raymo, M. Tomasulo, U.S. Pat. Appl. 20110095243: April 8, 2011
"A New Family of Photochromic Compounds Based on the Photoinduced Opening and Thermal Closing of [1,3]Oxazine Rings": M. Tomasulo, S. Sortino, F. M. Raymo, J. Photochem. Photobiol. A, 2008, 200, 44–49
"Fast and Stable Photochromic Oxazines for Fluorescence Switching": E. Deniz, M. Tomasulo, J. Cusido, S. Sortino, F. M. Raymo, Langmuir, 2011, 27, 11773–11783
The photoinduced opening and thermal closing of oxazine rings can be exploited to perform a full photochromic switching cycle on a timescale of nanoseconds with no sign of photobleaching.
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