Use of Halochromic Oxazine Compounds for Making Chromogenic Materials
Françisco Raymo and Massimiliano Tomasulo
Problem
This invention relates to color changing compounds. In particular, it relates to compounds that change color after paint or coating application. Examples of practical application of color changing compounds are adjusting color of paint after application to match adjacent areas, or changing article color completely for decorative purposes. Existing color changing chemical agents, such as those used for indicating acidity, are not stable to be used in painting applications and cannot be fine tuned for specific purposes. What is needed is a color adjustable compound that has high color adjustability and can maintain specified color for an extended time period, such as several months.
Solution
The present invention employs oxazine molecules that change color properties according to the pH of environment. Applying acidic solution to a paint coating composed of the oxazine compound will change the color of paint. The color will persist indefinitely unless a solution with basic pH is applied. The structure of the compounds can also be adjusted to fine tune their reversibility. For example, systems that fade in the rain by design, or systems that remain colored even after extensive washing with water can be engineered. Other mechanisms to control the color state of oxazine molecules may be explored as well.
Competitive Advantage
The invention offers a color adjustable compound that can be used in commercial paint products that will have high color adjustability and can maintain a specified color for an extended time period.
Applications
This invention can be used for temporarily or permanently changing colors of various articles.
Patent Status
International patent application entitled "USE OF HALOCHROMIC OXAZINE COMPOUNDS FOR MAKING CHROMOGENIC MATERIALS" was filed on October 17, 2008.
Licensing Opportunity
We are looking for a commercialization partner with capabilities in product development, sales, and marketing. An exclusive worldwide license is available.
About the Inventors
Françisco M. Raymo received a Laurea in Chemistry from the University of Messina (Italy) in 1992 and a Ph.D. in Chemistry from the University of Birmingham (UK) in 1996. He was a postdoctoral associate at the University of Birmingham (UK) in 1996-1997 and at the University of California, Los Angeles in 1997-1999. He was appointed Assistant Professor of Chemistry at the University of Miami in 2000 and promoted to Associate Professor in 2004. His research interests combine the design, synthesis, and analysis of functional molecule-based materials. Specifically, he is developing electroactive films, fluorescent probes and photochromic glasses for chemical sensing and signal processing applications. He is the author of more than 130 publications in the areas of chemical synthesis, computational chemistry, materials science, and supramolecular chemistry.
Massimiliano Tomasulo received a Laurea in Chemistry from the University of Bologna (Italy) in 1999 and a Ph.D. in Chemistry from the University of Miami in 2005. Currently, he is a postdoctoral associate in the research group of Professor Raymo. His research focuses on the design and synthesis of photochromic compounds, the electrochemical, photochemical and photophysical investigation of their behavior in solution, the entrapment of these molecules in rigid matrices, and the analysis of the optical properties of the resulting photochromic materials.
Selected References
"Signal Processing at the Molecular Level": F. M. Raymo, S. Giordani, J. Am. Chem. Soc., 2001, 123, 4651-4652
"Digital Communication through Intermolecular Fluorescence Modulation": F. M. Raymo, S. Giordani, Org. Lett., 2001, 3, 1833-1836
"Signal Communication between Molecular Switches": F. M. Raymo, S. Giordani, Org. Lett., 2001, 3, 3475-3478
"Multichannel Digital Transmission in an Optical Network of Communicating Molecules": F. M. Raymo, S. Giordani, J. Am. Chem. Soc., 2002, 124, 2004-2007
"All-Optical Processing with Molecular Switches": F. M. Raymo, S. Giordani, Proc. Natl. Acad. Sci. USA, 2002, 99, 4941-4944
"Supramolecular Association of Dopamine with Immobilized Fluorescent Probes": F. M. Raymo, M. A. Cejas, Org. Lett., 2002, 4, 3183-3185
"A Switch in a Cage with a Memory": S. Giordani, F. M. Raymo, Org. Lett., 2003, 5, 3559-3562
"Memory Effects Based on Intermolecular Photoinduced Proton Transfer": F. M. Raymo, R. J. Alvarado, S. Giordani, M. A. Cejas, J. Am. Chem. Soc., 2003, 125, 2361-2364
"Digital Processing with A Three-State Molecular Switch": F. M. Raymo, S. Giordani, A. J. P. White, D. J. Williams, J. Org. Chem., 2003, 68, 4158-4169
"Electron Transport in Self-Assembled Bipyridinium Multilayers": F. M. Raymo, R. J. Alvarado, E. J. Pacsial, D. Alexander, J. Phys. Chem. B, 2004, 108, 8622-8625
"Donor/Acceptor Interactions in Self-Assembled Monolayers and Their Consequences on Interfacial Electron Transfer": E. J. Pacsial, D. Alexander, R. J. Alvarado, M. Tomasulo, F. M. Raymo, J. Phys. Chem. B, 2004, 108, 19307-19313
"A Fast and Stable Photochromic Switch Based on the Opening and Closing of an Oxazine Ring": M. Tomasulo, S. Sortino, F. M. Raymo, Org. Lett., 2005, 7, 1109-1112
"Self-Assembling Bipyridinium Multilayers": R. J. Alvarado, J. Mukherjee, E. J. Pacsial, D. Alexander, F. M. Raymo, J. Phys. Chem. B, 2005, 109, 6164-6173
"Fluorescent Diazapyrenium Films and Their Response to Dopamine": M. A. Cejas, F. M. Raymo, Langmuir, 2005, 21, 5795-5802
"Fluorescence Modulation with Photochromic Switches": F. M. Raymo, M. Tomasulo, J. Phys. Chem. A, 2005, 109, 7343-7352
"Fast and Stable Photochromic Oxazines": M. Tomasulo, S. Sortino, A. J. P. White, F. M. Raymo, J. Org. Chem., 2005, 70, 8180-8189
"Colorimetric Detection of Cyanide with a Chromogenic Oxazine": M. Tomasulo, F. M. Raymo, Org. Lett., 2005, 7, 4633-4636
"Chromogenic Oxazines for Cyanide Detection": M. Tomasulo, S. Sortino, A. J. P. White, F. M. Raymo, J. Org. Chem., 2006, 71, 744-753
"pH-Sensitive Quantum Dots": M. Tomasulo, I. Yildiz, F. M. Raymo, J. Phys. Chem. B, 2006, 110, 3853-3855
"A Mechanism to Signal Receptor-Substrate Interactions with Luminescent Quantum Dots": I. Yildiz, M. Tomasulo, F. M. Raymo, Proc. Natl. Acad. Sci. USA, 2006, 103, 11457-11460
