Tuning the temperature dependence for switching in dithienylethene photochromic switches

Journal of Physical Chemistry A

Volumn 117, Issue 34, 2013, Pages 8222-8229

  Kudernac, Tibor ^a,e   Kobayashi, Takao ^b   Uyama, Ayaka ^c   Uchida, Kingo ^c   Nakamura, Shinichiro ^d   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b MITSUBISHI CHEMICAL CORPORATION   (Japan)

^c RYUKOKU UNIVERSITY   (Japan)

^d RIKEN   (Japan)

^e UNIVERSITY OF TWENTE   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROCYCLIZATION REACTIONS; IMPLICATIONS FOR FUTURES; PHOTOCHEMICAL SWITCHING; PHOTOCHROMIC SWITCHES; STRUCTURAL VARIATIONS; SWITCHING EFFICIENCY; TEMPERATURE DEPENDENCE; THERMAL ACTIVATION;

EFFICIENCY; ISOMERS; OLEFINS; OPTIMIZATION; PHOTOCHROMISM; QUANTUM CHEMISTRY; STRUCTURAL DESIGN; TEMPERATURE DISTRIBUTION;

SWITCHING;

EID: 84883330305     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp404924q     Document Type: Conference Paper

References (48)

1. Molecular Switches; Feringa, B. L., Ed.; Wiley-VCH: Weinheim, Germany, 2001.
2. Crano, J. C.; Guglielmetti, R. Organic Photochromic and Thermochromic Compounds; Plenum Press: New York, 1999; Vol. 1.
3. Irie, M. Diarylethenes for Memories and Switches Chem. Rev. 2000, 100, 1685-1716
4. Irie, M.; Fukaminato, T.; Sasaki, T.; Tamai, N.; Kawai, T. A Digital Fluorescent Molecular Photoswitch Nature 2002, 420, 759-760
5. Norsten, T. B.; Branda, N. R. Photoregulation of Fluorescence in a Porphyrinic Dithienylethene Photochrome J. Am. Chem. Soc. 2001, 123, 1784-1785
6. Tsivogulis, G. M.; Lehn, J. -M. Reversibly Photoswitchable Fluorophores for Non-Destructive Readout for Optical Memory Angew. Chem., Int. Ed. 1995, 34, 1119-1122
7. Tian, H.; Chen, B. Z.; Tu, H. Y.; Mullen, K. Novel Bisthienylethene-Based Photochromic Tetraazaporphyrin with Photoregulating Luminescence Adv. Mater. 2002, 14, 918-923
8. Luo, Q. F.; Chen, B. Z.; Wang, M. Z.; Tian, H. Mono-Bisthienylethene Ring-Fused versus Multi-Bisthienylethene Ring-Fused Photochromic Hybrids Adv. Funct. Mater. 2003, 13, 233-239
9. Tian, H.; Qin, B.; Yao, R. X.; Zhao, X. L.; Yang, S. J. A Single Photochromic Molecular Switch with Four Optical Outputs Probing Four Inputs Adv. Mater. 2003, 15, 2104
10. Matsuda, K.; Irie, M. Photoswitching of Intramolecular Magnetic Interaction Using a Photochromic Spin Coupler: An ESR Study J. Am. Chem. Soc. 2000, 122, 8309-8310
11. Fraysse, S.; Coudret, C.; Launay, J. P. Synthesis and Properties of Dinuclear Complexes with a Photochromic Bridge: An Intervalence Electron Transfer Switching "On" and "Off" Eur. J. Inorg. Chem. 2000, 1581-1590
12. Kudernac, T.; Katsonis, N.; Browne, W. R.; Feringa, B. L. Nano-Electronic Switches: Light-Induced Switching of the Conductance of Molecular Systems J. Mater. Chem. 2009, 19, 7168-7177
13. Katsonis, N.; Kudernac, T.; Walko, M.; van der Molen, S. J.; van Wees, B. J.; Feringa, B. L. Reversible Conductance Switching of Single Diarylethenes on a Gold Surface Adv. Mater. 2006, 18, 1397-1400
14. He, J.; Chen, F.; Liddell, P. A.; Andreasson, J.; Straight, S. D.; Gust, D.; Moore, T. A.; Moore, A. L.; Li, J.; Sankey, O. F.; Lindsay, S. M. Switching of a Photochromic Molecule on Gold Electrodes: Single-Molecule Measurements Nanotechnology 2005, 16, 695-702
15. Matsuda, K.; Yamaguchi, H.; Sakano, T.; Ikeda, M.; Tanifuji, N.; Irie, M. Conductance Photoswitching of Diarylethene-Gold Nanoparticle Network Induced by Photochromic Reaction J. Phys. Chem. C 2008, 112, 17005-17010
16. Dulic, D.; van der Molen, S. J.; Kudernac, T.; Jonkman, H. T.; de Jong, J. J. D.; Bowden, T. N.; van Esch, J.; Feringa, B. L.; van Wees, B. J. One-Way Optoelectronic Switching of Photochromic Molecules on Gold Phys. Rev. Lett. 2003, 91, 207402
17. Gilat, S. L.; Kawai, S. H.; Lehn, J.-M. Photochemical Switching of Optical and Electrochemical Properties in Molecular Wire Type Diarylethene Species Chem.-Eur. J. 1995, 1, 275-284
18. Peters, A.; Branda, N. R. Electrochromism in Photochromic Dithienylcyclopentenes J. Am. Chem. Soc. 2003, 125, 3404-3405
19. Browne, W. R.; de Jong, J. J. D.; Kudernac, T.; Walko, M.; Lucas, L. N.; Uchida, K.; van Esch, J. H.; Feringa, B. L. Oxidative Electrochemical Switching in Dithienylcyclopentenes: Effect of Electronic Perturbation on the Efficiency and Direction of Molecular Switching Chem.-Eur. J. 2005, 11, 6414-6429
20. Areephong, J.; Browne, W. R.; Katsonis, N.; Feringa, B. L. Photo- and Electro-chromism of Diarylethene Modified ITO Electrodes-Towards Molecular Based Read-Write-Erase Information Storage Chem. Commun. 2006, 3930-3932
21. Murguly, E.; Norsten, T. B.; Branda, N. R. Nondestructive Data Processing Based on Chiroptical 1,2-Dithienylethene Photochromes Angew. Chem., Int. Ed. 2001, 40, 1752-1755
22. Irie, M.; Kobatake, S.; Horichi, M. Reversible Surface Morphology Changes of a Photochromic Diarylethene Single Crystal by Photoirradiation Science 2001, 291, 1769-1772
23. Kobatake, S.; Takami, S.; Muto, H.; Ishikawa, T.; Irie, M. Rapid and Reversible Shape Changes of Molecular Crystals on Photoirradiation Nature 2007, 446, 778-781
24. Uchida, K.; Sukata, S. I.; Matsuzawa, Y.; Akazawa, M.; de Jong, J. J. D.; Katsonis, N.; Kojima, Y.; Nakamura, S.; Areephong, J.; Meetsma, A. Photoresponsive Rolling and Bending of Thin Crystals of Chiral Diarylethenes Chem. Commun. 2008, 326-328
25. de Jong, J. J. D.; Lucas, L. N.; Kellogg, R. M.; van Esch, J. H.; Feringa, B. L. Reversible Optical Transcription of Supramolecular Chirality into Molecular Chirality Science 2004, 304, 278-281
26. Zhang, P.; Buncel, E.; Lemieux, R. P. Compatibilization of a Photochromic Dithienylethene Dopant and Ferroelectric Liquid-Crystal Host via Siloxane Nanosegregation Adv. Mater. 2005, 17, 567-571
27. Maly, K. E.; Wand, M. D.; Lemieux, R. P. Bistable Ferroelectric Liquid Crystal Photoswitch Triggered by a Dithienylethene Dopant J. Am. Chem. Soc. 2002, 124, 7898-7899
28. Frigoli, M.; Welch, C.; Mehl, G. H. Design of Mesomorphic Diarylethene-Based Photochromes J. Am. Chem. Soc. 2004, 126, 15382-15383
29. Dulic, D.; Kudernac, T.; Pugzlys, A.; Feringa, B. L.; van Wees, B. J. Temperature Gating of the Ring-Opening Process in Diarylethene Molecular Switches Adv. Mater. 2007, 19, 2898-2902
30. Nakamura, S.; Kobayashi, T.; Takata, A.; Uchida, K.; Asano, Y.; Murakami, A.; Goldberg, A.; Guillaumont, D.; Yokojima, S.; Kobatake, S. Quantum Yields and Potential Energy Surfaces: A Theoretical Study J. Phys. Org. Chem. 2007, 20, 821-829
31. Uchida, K.; Tsuchida, E.; Aoi, Y.; Nakamura, S.; Irie, M. Substituent Effect on the Coloration Quantum Yield of a Photochromic Bisbenzothienylethene Chem. Lett. 1999, 63-64
32. Irie, M.; Lifka, T.; Kobatake, S.; Kato, N. Photochromism of 1,2-Bis(2-methyl-5-phenyl-3-thienyl)perfluorocyclopentene in a Single-Crystalline Phase J. Am. Chem. Soc. 2000, 122, 4871-4876
33. Uchida, K.; Matsuoka, T.; Kobatake, S.; Yamaguchi, T.; Irie, M. Substituent Effect on the Photoreactivity of Bis(2-thienyl) perfluorocyclopentenes Tetrahedron 2001, 57, 4559-4565
34. Irie, M.; Sakemura, K.; Okinaka, M.; Uchida, K. Photochromism of Dithienylethenes with Electron-Donating Substituents J. Org. Chem. 1995, 60, 8305-8309
35. Woodward, R. B.; Hoffmann, R. Stereochemistry of Electrocyclic Reactions J. Am. Chem. Soc. 1965, 87, 395-397
36. Nakamura, S.; Irie, M. Thermally Irreversible Photochromic Systems. A Theoretical Study J. Org. Chem. 1988, 53, 6136-6138
37. Asano, Y.; Murakami, A.; Kobayashi, T.; Goldberg, A.; Guillaumont, D.; Yabushita, S.; Irie, M.; Nakamura, S. Theoretical Study on the Photochromic Cycloreversion Reactions of Dithienylethenes, on the Role of the Conical Intersections J. Am. Chem. Soc. 2004, 126, 12112-12120
38. Guillaumont, D.; Kobayashi, T.; Kanda, K.; Miyasaka, H.; Uchida, K.; Kobatake, S.; Shibata, S.; Nakamura, S.; Irie, M. An Ab Initio MO Study of the Photochromic Reaction of Dithenylethenes J. Phys. Chem. A 2002, 106, 7222
39. Staykov, A.; Areephong, J.; Browne, W. R.; Feringa, B. L.; Yoshizawa, K. Electrochemical and Photochemical Cyclization and Cycloreversion of Diarylethenes and Diarylethene-Capped Sexithiophene Wires ACS Nano 2011, 5, 1165-1178
40. Nakamura, S.; Yokojima, S.; Uchida, K.; Tsujioka, T.; Goldberg, A.; Murakami, A.; Shinoda, K.; Mikami, M.; Kobayashi, T.; Kobatake, S. Theoretical Investigation on Photochromic Diarylethene, a Short Review J. Photochem. Photobiol., A 2008, 200, 10-18
41. Tatsumi, Y.; Kitai, J.; Uchida, W.; Ogata, K.; Nakamura, S.; Uchida, K. Photochromism of 1,2-Bis(2-thienyl)perfluorocyclopentene Derivatives: Substituent Effect on the Reactive Carbon Atoms J. Phys. Chem. A 2012, 116, 10973-10979
42. Perrier, A.; Aloise, S.; Olivucci, M.; Jacquemin, D. Inverse versus Normal Dithienylethenes: Computational Investigation of the Photocyclization Reaction J. Phys. Chem. Lett. 2013, 4, 2190-2196
43. 2-symmetric avoided crossing region; see: van der Lugt, W. T. A. M.; Oosterhoff, L. J. Symmetry Control and Photoinduced Reactions J. Am. Chem. Soc. 1969, 91, 6042-6049
44. Garavelli, M.; Page, C. S.; Celani, P.; Olivucci, M.; Schmid, W. E.; Trushin, S. A.; Fuß, W. Reaction Path of a Sub-200 fs Photochemical Electrocyclic Reaction J. Phys. Chem. A 2001, 105, 4458-4469
45. Proceedings of ICCMSE 2007, volume 2, parts A and B; AIP Conference Proceedings, 2007; Vol. 963, pp 338-341.
46. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Gaussian 03, revision C.02, Gaussian, Inc.: Wallingford, CT, 2004.
47. Yokoyama, Y.;; Kurita, Y. Synthesis and Photoreaction of Photochromic Fulgides. J. Synth. Org. Chem. 1991, 49, 364-372 (in Japanese).
48. Uchida, K.; Sumino, H.; Shimobayashi, Y.; Ushiogi, Y.; Takata, A.; Kojima, Y.; Yokojima, S.; Kobatake, S.; Nakamura, S. Unusual Photochromic Behavior of C3-Methoxy-Substituted Bis(2-thienyl)perfluorocyclopentene Bull. Chem. Soc. Jpn. 2009, 82, 1441-1446