Ab initio investigation of the electronic properties of coupled dithienylethenes

Journal of Physical Chemistry Letters

Volumn 1, Issue 1, 2010, Pages 434-438

  Jacquemin, Denis ^a   Perpète, Eric A ^b   Maurel, François ^b   Perrier, Aurélie ^b  

^a UNIVERSITY OF NAMUR   (Belgium)

^b UNIVERSITÉ PARIS DIDEROT   (France)

Author keywords

Electron transport; Hard matter; Optical and electronic devices

Indexed keywords

AB INITIO; AB INITIO INVESTIGATION; CLOSED FORM; CONJUGATED BRIDGES; DITHIENYLETHENE; ELECTRON TRANSPORT; ELECTRONIC DEVICE; MOLECULAR SWITCHES; PHOTOCHROMES; REFINED STRUCTURES; SPECTRAL PROPERTIES; TIME-DEPENDENT;

ELECTRON TRANSITIONS; ELECTRON TRANSPORT PROPERTIES; ELECTRONIC PROPERTIES; THERMOELECTRIC EQUIPMENT;

DENSITY FUNCTIONAL THEORY;

EID: 77149121827     PISSN: None     EISSN: 19487185     Source Type: Journal    
DOI: 10.1021/jz900293g     Document Type: Article

References (29)

1. Irie, M. Diarylethenes for Memories and Switches. Chem. Rev. 2000, 100, 1685-1716.
2. Matsuda, K.; Irie, M. Photochromism of Diarylethenes with Two Nitronyl Nitroxides: Photoswitching of an Intramolecular Magnetic Interaction. Chem.-Eur. J. 2001, 7, 3466-3473.
3. Guirado, G.; Coudret, C.; Launay, J.-P. Electrochemical Remote Control for Dithienylethene-Ferrocene Switches J. Phys. Chem. C 2007, 111, 2770-2776.
4. Kobatake, S.; Takami, D.; Muto, H.; Ishikawa, T.; Irie, M. Rapid and Reversible Shape Changes of Molecular Crystals on Photoirradiation. Nature 2007, 446, 778-781.
5. Mrozek, T.; Görner, H.; Daub, J. Towards Multifold Cycloswitching of Biphotochromes: Investigation on a Bond-Fused Dihydroazulene/Vinylheptafulvene and Dithienylethene/Dihydrothienobenzothiophene. Chem. Commun. 1999, 1487-1488.
6. Frigoli, M.; Mehl, G. H. Multiple Addressing in a Hybrid Biphotochromic System. Angew. Chem., Int. Ed. 2005, 44, 5048-5052.
7. Peters, A.; Branda, N. R. Linked Photochromism in Covanlently Linked Double 1,2-Dithienylethenes. Adv. Mater. Opt. Electron. 2000, 10, 245-249.
8. Matsuda, K.; Irie, M. Photoswitching of Intramolecular Magnetic Interaction Using a Diarylethene Dimer J. Am. Chem. Soc. 2001, 123, 9896-9897.
9. Kawai, S. H.; Sasaki, T.; Irie, M. A Photoresponsive Laser Dye Containing Photochromic Dithienylethene Units. Chem. Commun. 2001, 711-712.
10. Kaieda, T.; Kobatake, S.; Miyasaka, H.; Murakami, M.; Iwai, N.; Nagata, Y.; Itaya, A.; Irie, M. Efficient Photocyclization of Dithienylethene Dimer, Trimer, and Tetramer: Quantum Yield and Reaction Dynamics J. Am. Chem. Soc. 2002, 124, 2015-2024.
11. Kobatake, S.; Irie, M. Synthesis and Photochromic Reactivity of a Diarylethene Dimer Linked by a Phenyl Group. Tetrahedron 2003, 59, 8359-8364.
12. Jung, I.; Choi, H.; Kim, E.; Lee, C. H.; Kang, S. O.; Ko, J. Synthesis and Photochromic Reactivity of Macromolecules Incorporating Four Dithienyletehene Units. Tetrahedron 2005, 61, 12256-12263.
13. Areephong, J.; Browne, W. R.; Feringa, B. L. Three-State Photochromic Switching in a Silyl Bridged Diarylethene Dimer. Org. Biomol. Chem. 2007, 5, 1170-1174.
14. Ko, C. C.; Lam, W. H.; Yam, V. W. W. Photochromic Oligothienoacene Derivatives with Photo-Switchable Luminescence Properties and Computational Studies. Chem. Commun. 2008, 5203-5205.
15. Areephong, J.; Hurenkamp, J. H.; Milder, M. T. W.; Meetsma, A.; Herek, J. L.; Browne, W. R.; Feringa, B. L. Photoswitchable Sexithiophene-Based Molecular Wires. Org. Lett. 2009, 11, 721-724.
16. Zhong, Y. W.; Vila, N.; Henderson, J. C.; Abruna, H. D. Dithienylcyclopentenes-Containing Transition Metal Bisterpyridine Complexes Directed toward Molecular Electronic Applications. Inorg. Chem. 2009, 48, 991-999.
17. Kim, H. E.; Jang, J. H.; Choi, H.; Lee, T.; Ko, J.; Yoon, M.; Kim, H. J. Photoregulated Fluorescence Switching in Axially Coordinated Tin(IV) Porphyrinic Dithienylethene. Inorg. Chem. 2008, 47, 2411-2415.
18. Zhong, Y. W.; Vila, N.; Henderson, J. C.; Abruna, H. D. Transition-Metal Tris-Bipyridines Containing Three Dithienylcyclopentenes: Synthesis, Photochromic, and Electronic Properties. Inorg. Chem. 2009, 48, 7080-7085.
19. Perrier, A.; Maurel, F.; Aubard, J. Theoretical Investigation of the Substituent Effect on the Electronic and Optical Properties of Photochromic Dithienylethene Derivatives. J. Photochem. Photobiol., A 2007, 189, 167-176.
20. Maurel, F.; Perrier, A.; Perpète, E. A.; Jacquemin, D.A Theoretical Study of the Perfluoro-Diarylethenes Electronic Spectra J. Photochem. Photobiol., A 2008, 199, 211-223.
21. Chen, D. Z.; Wang, Z.; Zhao, X. Theoretical Study on Geometric Electronic Structures and Absorption Wavelengths Properties of Closed-Ring Isomers of Diarylmaleic Anhydres J. Mol. Struct.: THEOCHEM 2006, 774, 77-81.
22. Patel, P. D.; Masunov, A. E. Theoretical Study of Photochromic Compounds. 1. Bond Length Alternation and Absorption Spectra for the Open and Closed Forms of 29 Diarylethene Derivatives J. Phys. Chem. A 2009, 113, 8409-8414.
23. Choi, H.; Jung, I.; Song, K. H.; Song, K.; Shin, D. S.; Kang, S. O.; Ko, J. Synthesis and Photochromic Reactivity of Diarylethene Trimers Bridged by Ethenyl and Ethynyl Unit. Tetrahedron 2006, 62, 9059-9065.
24. Laurent, A. D.; Andrè, J. M.; Perpète, E. A.; Jacquemin, D. Photochromic Properties of Dithienylazoles and Other Conjugated Diarylethenes. J. Photochem. Photobiol., A 2007, 192, 211-219.
25. Jacquemin, D.; Perpète, E. A.; Ciofini, I.; Adamo, C. Accurate Simulation of Optical Properties in Dyes. Acc. Chem. Res. 2009, 42, 326-334.
26. Frisch, M. J.; et al. Gaussian 03, revisions D.02 and E.01; Gaussian, Inc.: Wallingford, CT, 2004.
27. Jacquemin, D.; Perpète, E. A. Ab Initio Calculations of the Colour of Closed-Ring Diarylethenes: TD-DFT Estimates for Molecular Switches Chem. Phys. Lett. 2006, 429, 147-152.
28. Tomasi, J.; Mennucci, B.; Cammi, R. Quantum Mechanical Continuum Solvation Models Chem. Rev. 2005, 105, 2999-3094.
29. Adamo, C.; Barone, V. Toward Reliable Density Functional Methods Without Adjustable Parameters: the PBE0 Model J. Chem. Phys. 1999, 110, 6158-6170.