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


Selected Articles

  "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, 1188811895


Patents

   "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


Selected Reviews

  "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.