Influence of the solvent on the thermal back reaction of one spiropyran

Journal of Chemical Education

Volumn 91, Issue 12, 2014, Pages 2105-2111

  Piard, Jonathan ^a  

^a Ecole Normale Superieure de Cachan   (France)

Author keywords

First year undergraduate general; Hands on learning manipulatives; Photochemistry; Physical chemistry; Second year undergraduate; UV Vis spectroscopy

Indexed keywords

EID: 84916623742     PISSN: 00219584     EISSN: 19381328     Source Type: Journal    
DOI: 10.1021/ed4005003     Document Type: Article

References (31)

1. Braslavsky, S. E. Glossary of Terms Used in Photochemistry. Pure Appl. Chem. 2007, 79 (3), 293-465.
2. Brown, G. H. Photochromism ; Wiley-Interscience: New York, 1971; p 853.
3. Dürr, H.; Bouas-Laurent, H. Photochromism, Molecules, and Systems ; Elsevier: Amsterdam, 1990.
4. Feringa, B. L.; Delden, R. A.; Wiel, M. K. J., Chiroptical Molecular Switches. In Molecular Switches; Feringa, B. L., Ed.; Wiley-VCH: Darmstadt, 2001.
5. Osterby, B.; McKelvey, R. D.; Hill, L. Photochromic Sunglasses: A Patent-Based Advanced Organic Synthesis Project and Demonstration. J. Chem. Educ. 1991, 68, 424-425.
6. Dvornikov, A. S.; Walker, E. P.; Rentzepis, P. M. Two-Photon Three-Dimensional Optical Storage Memory. J. Phys. Chem. A 2009, 113 (49), 13633-13644.
7. Parthenopoulos, D. A.; Rentzepis, P. M. 3-Dimensional Optical Storage Memory. Science 1989, 245 (4920), 843-845.
8. Raymo, F. M.; Giordani, S.; White, A. J. P.; Williams, D. J. Digital Processing with a Three-State Molecular Switch. J. Org. Chem. 2003, 68 (11), 4158-4169.
9. Raymo, F. M.; Tomasulo, M. Electron and Energy Transfer Modulation with Photochromic Switches. Chem. Soc. Rev. 2005, 34 (4), 327-336.
10. Zhu, L. Y.; Wu, W. W.; Zhu, M. Q.; Han, J. J.; Hurst, J. K.; Li, A. D. Q. Reversibly Photoswitchable Dual-Color Fluorescent Nanoparticles As New Tools for Live-Cell Imaging. J. Am. Chem. Soc. 2007, 129 (12), 3524-3526.
11. Zhu, M. Q.; Zhang, G. F.; Li, C.; Aldred, M. P.; Chang, E.; Drezek, R. A.; Li, A. D. Q. Reversible Two-Photon Photoswitching and Two-Photon Imaging of Immunofunctionalized Nanoparticles Targeted to Cancer Cells. J. Am. Chem. Soc. 2011, 133 (2), 365-372.
12. Irie, M.; Fukaminato, T.; Sasaki, T.; Tamai, N.; Kawai, T. Organic Chemistry: A Digital Fluorescent Molecular Photoswitch. Nature 2002, 420 (6917), 759-760.
13. Kawai, T.; Sasaki, T.; Irie, M. A Photoresponsive Laser Dye Containing Photochromic Dithienylethene Units. Chem. Commun. 2001, No. 8, 711-712.
14. Norsten, T. B.; Peters, A.; McDonald, R.; Wang, M. T.; Branda, N. R. Reversible [7]-Thiahelicene Formation Using a 1,2-Dithienylcyclopentene Photochrome. J. Am. Chem. Soc. 2001, 123 (30), 7447-7448.
15. Chauvin, J.; Kawai, T.; Irie, M. Refractive Index Change of an Amorphous Bisbenzothienylethene. Jpn. J. Appl. Phys., Part 1 2001, 40 (4A), 2518-2522.
16. Kawai, T.; Fukuda, N.; Groschl, D.; Kobatake, S.; Irie, M. Refractive Index Change of Dithienylethene in Bulk Amorphous Solid Phase. Jpn. J. Appl. Phys., Part 2 1999, 38 (10B), L1194-L1196.
17. Kim, E.; Choi, Y. K.; Lee, M. H. Photoinduced Refractive Index Change of a Photochromic Diarylethene Polymer. Macromolecules 1999, 32 (15), 4855-4860.
18. Kim, M. S.; Maruyama, H.; Kawai, T.; Irie, M. Refractive Index Changes of Amorphous Diarylethenes Containing 2,4-Diphenylphenyl Substituents. Chem. Mater. 2003, 15 (24), 4539-4543.
19. Gilat, S. L.; Kawai, S. H.; Lehn, J. M. Light-Triggered Molecular Devices - Photochemical Switching of Optical and Electrochemical Properties in Molecular Wire Type Diarylethene Species. Chem. - Eur. J. 1995, 1 (5), 275-284.
20. Kawai, T.; Kunitake, T.; Irie, M. Novel Photochromic Conducting Polymer Having Diarylethene Derivative in the Main Chain. Chem. Lett. 1999, 9, 905-906.
21. Matsuda, K.; Irie, M. A Diarylethene with Two Nitronyl Nitroxides: Photoswitching of Intramolecular Magnetic Interaction. J. Am. Chem. Soc. 2000, 122 (30), 7195-7201.
22. Guglielmetti, R.; Meyer, R.; Dupuy, C. J. Synthesis of a Photochromic Benzothiazolinic Spiropyran. J. Chem. Educ. 1973, 50, 413-415.
23. Byrne, J. P. Thermodynamic Data from the Thermochromic Effect. J. Chem. Educ. 1978, 55, 267-268.
24. Chambers, K. W.; Smith, I. M. An Inexpensive Flash Photolysis Apparatus and Demonstration Experiment. J. Chem. Educ. 1974, 51, 354-356.
25. Jacques, P. Synergistic Effects in Binary Solvent Mixtures. A Simple Approach to a Special Case of Nonideal Binary Mixture Behavior. J. Chem. Educ. 1991, 68, 347-348.
26. Prypsztejn, H. R.; Martín Negri, R. An Experiment on Photochromism and Kinetics for the Undergraduate Laboratory. J. Chem. Educ. 2001, 78, 645-648.
27. Calvert, J. G.; Pitts, J. N., Jr. Photochemistry; Wiley and Sons: New York, 1966; p 487.
28. Sigma Aldrich Web Page. http://www.sigmaaldrich.com (accessed Aug 2014).
29. Acros Organics Web Page. http://www.acros.com (accessed Aug 2014).
30. Shah, S. S.; Henscheid, L. G. Absorption Spectroscopy in Homogeneous and Micellar solutions. J. Chem. Educ. 1983, 60, 685-687.
31. Flannery, J. B. J. Photo- and Thermochromic Transients from Substituted 1′,3′,3′-Trimethylindolinobenzospiropyrans. J. Am. Chem. Soc. 1968, 90, 5660-5671.