Electrochromism in photochromic dithienylcyclopentenes

Journal of the American Chemical Society

Volumn 125, Issue 12, 2003, Pages 3404-3405

  Peters, Andrea ^a   Branda, Neil R ^a  

^a SIMON FRASER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 BIS[5',2' BIS(THIOPHEN 2 YL)THIEN 3' YL]FLUOROCYCLOPENTENE; 1,2 DITHIENYLCYCLOPENTENE DERIVATIVE; AROMATIC COMPOUND; CARBON; CYCLOPENTENE DERIVATIVE; HETEROCYCLIC COMPOUND; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; COLOR; CONJUGATION; CYCLIC POTENTIOMETRY; ELECTRIC POTENTIAL; ELECTROCHEMICAL ANALYSIS; ELECTROLYSIS; ISOMER; OXIDATION; OXIDATION REDUCTION REACTION; PHOTOSTIMULATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; RING CLOSING METATHESIS; RING OPENING;

EID: 0037467425     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028764x     Document Type: Article

References (18)

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5. For an overview of electrochromism, see: Electrochromism: Fundamentals and Applications; Monk, P. M. S., Mortimer, R. J., Rosseinky, D. R., Eds.; VHC: New York, 1995. For examples of electrochemically gated photochromic systems, see: (a) Miki, S.; Noda, R.; Fukunishi, K. Chem. Commun. 1997, 925. (b) Zhi, J.-F.; Baba, R.; Hashimoto, K.; Fujishima, A. J. Photochem. Photobiol., A 1995, 92, 91. (c) Zhi, J.-F.; Baba, R.; Hashimoto, K.; Fujishima, A. Ber. Bunsen-Ges. Phys. Chem. 1995, 99, 32. (d) Kawai, S. H.; Gilat, S. L.; Ponsinet, R.; Lehn, J.-M. Chem.-Eur. J. 1995, 1, 285. (e) Saika, T.; Iyoda, T.; Honda, K.; Shimidzu, T. J. Chem. Soc., Perkin Trans. 2 1993, 1181. (f) Newell, A. K.; Utley, J. H. P. J. Chem. Soc., Chem. Commun. 1992, 800. (g) Iyoda, T.; Saika, T.; Honda, K.; Shimidzu, T. Tetrahedron Lett. 1989, 30, 5429.
6. For an overview of electrochromism, see: Electrochromism: Fundamentals and Applications; Monk, P. M. S., Mortimer, R. J., Rosseinky, D. R., Eds.; VHC: New York, 1995. For examples of electrochemically gated photochromic systems, see: (a) Miki, S.; Noda, R.; Fukunishi, K. Chem. Commun. 1997, 925. (b) Zhi, J.-F.; Baba, R.; Hashimoto, K.; Fujishima, A. J. Photochem. Photobiol., A 1995, 92, 91. (c) Zhi, J.-F.; Baba, R.; Hashimoto, K.; Fujishima, A. Ber. Bunsen-Ges. Phys. Chem. 1995, 99, 32. (d) Kawai, S. H.; Gilat, S. L.; Ponsinet, R.; Lehn, J.-M. Chem.-Eur. J. 1995, 1, 285. (e) Saika, T.; Iyoda, T.; Honda, K.; Shimidzu, T. J. Chem. Soc., Perkin Trans. 2 1993, 1181. (f) Newell, A. K.; Utley, J. H. P. J. Chem. Soc., Chem. Commun. 1992, 800. (g) Iyoda, T.; Saika, T.; Honda, K.; Shimidzu, T. Tetrahedron Lett. 1989, 30, 5429.
7. For an overview of electrochromism, see: Electrochromism: Fundamentals and Applications; Monk, P. M. S., Mortimer, R. J., Rosseinky, D. R., Eds.; VHC: New York, 1995. For examples of electrochemically gated photochromic systems, see: (a) Miki, S.; Noda, R.; Fukunishi, K. Chem. Commun. 1997, 925. (b) Zhi, J.-F.; Baba, R.; Hashimoto, K.; Fujishima, A. J. Photochem. Photobiol., A 1995, 92, 91. (c) Zhi, J.-F.; Baba, R.; Hashimoto, K.; Fujishima, A. Ber. Bunsen-Ges. Phys. Chem. 1995, 99, 32. (d) Kawai, S. H.; Gilat, S. L.; Ponsinet, R.; Lehn, J.-M. Chem.-Eur. J. 1995, 1, 285. (e) Saika, T.; Iyoda, T.; Honda, K.; Shimidzu, T. J. Chem. Soc., Perkin Trans. 2 1993, 1181. (f) Newell, A. K.; Utley, J. H. P. J. Chem. Soc., Chem. Commun. 1992, 800. (g) Iyoda, T.; Saika, T.; Honda, K.; Shimidzu, T. Tetrahedron Lett. 1989, 30, 5429.
8. For an overview of electrochromism, see: Electrochromism: Fundamentals and Applications; Monk, P. M. S., Mortimer, R. J., Rosseinky, D. R., Eds.; VHC: New York, 1995. For examples of electrochemically gated photochromic systems, see: (a) Miki, S.; Noda, R.; Fukunishi, K. Chem. Commun. 1997, 925. (b) Zhi, J.-F.; Baba, R.; Hashimoto, K.; Fujishima, A. J. Photochem. Photobiol., A 1995, 92, 91. (c) Zhi, J.-F.; Baba, R.; Hashimoto, K.; Fujishima, A. Ber. Bunsen-Ges. Phys. Chem. 1995, 99, 32. (d) Kawai, S. H.; Gilat, S. L.; Ponsinet, R.; Lehn, J.-M. Chem.-Eur. J. 1995, 1, 285. (e) Saika, T.; Iyoda, T.; Honda, K.; Shimidzu, T. J. Chem. Soc., Perkin Trans. 2 1993, 1181. (f) Newell, A. K.; Utley, J. H. P. J. Chem. Soc., Chem. Commun. 1992, 800. (g) Iyoda, T.; Saika, T.; Honda, K.; Shimidzu, T. Tetrahedron Lett. 1989, 30, 5429.
9. For an overview of electrochromism, see: Electrochromism: Fundamentals and Applications; Monk, P. M. S., Mortimer, R. J., Rosseinky, D. R., Eds.; VHC: New York, 1995. For examples of electrochemically gated photochromic systems, see: (a) Miki, S.; Noda, R.; Fukunishi, K. Chem. Commun. 1997, 925. (b) Zhi, J.-F.; Baba, R.; Hashimoto, K.; Fujishima, A. J. Photochem. Photobiol., A 1995, 92, 91. (c) Zhi, J.-F.; Baba, R.; Hashimoto, K.; Fujishima, A. Ber. Bunsen-Ges. Phys. Chem. 1995, 99, 32. (d) Kawai, S. H.; Gilat, S. L.; Ponsinet, R.; Lehn, J.-M. Chem.-Eur. J. 1995, 1, 285. (e) Saika, T.; Iyoda, T.; Honda, K.; Shimidzu, T. J. Chem. Soc., Perkin Trans. 2 1993, 1181. (f) Newell, A. K.; Utley, J. H. P. J. Chem. Soc., Chem. Commun. 1992, 800. (g) Iyoda, T.; Saika, T.; Honda, K.; Shimidzu, T. Tetrahedron Lett. 1989, 30, 5429.
10. For an overview of electrochromism, see: Electrochromism: Fundamentals and Applications; Monk, P. M. S., Mortimer, R. J., Rosseinky, D. R., Eds.; VHC: New York, 1995. For examples of electrochemically gated photochromic systems, see: (a) Miki, S.; Noda, R.; Fukunishi, K. Chem. Commun. 1997, 925. (b) Zhi, J.-F.; Baba, R.; Hashimoto, K.; Fujishima, A. J. Photochem. Photobiol., A 1995, 92, 91. (c) Zhi, J.-F.; Baba, R.; Hashimoto, K.; Fujishima, A. Ber. Bunsen-Ges. Phys. Chem. 1995, 99, 32. (d) Kawai, S. H.; Gilat, S. L.; Ponsinet, R.; Lehn, J.-M. Chem.-Eur. J. 1995, 1, 285. (e) Saika, T.; Iyoda, T.; Honda, K.; Shimidzu, T. J. Chem. Soc., Perkin Trans. 2 1993, 1181. (f) Newell, A. K.; Utley, J. H. P. J. Chem. Soc., Chem. Commun. 1992, 800. (g) Iyoda, T.; Saika, T.; Honda, K.; Shimidzu, T. Tetrahedron Lett. 1989, 30, 5429.
11. For an overview of electrochromism, see: Electrochromism: Fundamentals and Applications; Monk, P. M. S., Mortimer, R. J., Rosseinky, D. R., Eds.; VHC: New York, 1995. For examples of electrochemically gated photochromic systems, see: (a) Miki, S.; Noda, R.; Fukunishi, K. Chem. Commun. 1997, 925. (b) Zhi, J.-F.; Baba, R.; Hashimoto, K.; Fujishima, A. J. Photochem. Photobiol., A 1995, 92, 91. (c) Zhi, J.-F.; Baba, R.; Hashimoto, K.; Fujishima, A. Ber. Bunsen-Ges. Phys. Chem. 1995, 99, 32. (d) Kawai, S. H.; Gilat, S. L.; Ponsinet, R.; Lehn, J.-M. Chem.-Eur. J. 1995, 1, 285. (e) Saika, T.; Iyoda, T.; Honda, K.; Shimidzu, T. J. Chem. Soc., Perkin Trans. 2 1993, 1181. (f) Newell, A. K.; Utley, J. H. P. J. Chem. Soc., Chem. Commun. 1992, 800. (g) Iyoda, T.; Saika, T.; Honda, K.; Shimidzu, T. Tetrahedron Lett. 1989, 30, 5429.
12. For an overview of electrochromism, see: Electrochromism: Fundamentals and Applications; Monk, P. M. S., Mortimer, R. J., Rosseinky, D. R., Eds.; VHC: New York, 1995. For examples of electrochemically gated photochromic systems, see: (a) Miki, S.; Noda, R.; Fukunishi, K. Chem. Commun. 1997, 925. (b) Zhi, J.-F.; Baba, R.; Hashimoto, K.; Fujishima, A. J. Photochem. Photobiol., A 1995, 92, 91. (c) Zhi, J.-F.; Baba, R.; Hashimoto, K.; Fujishima, A. Ber. Bunsen-Ges. Phys. Chem. 1995, 99, 32. (d) Kawai, S. H.; Gilat, S. L.; Ponsinet, R.; Lehn, J.-M. Chem.-Eur. J. 1995, 1, 285. (e) Saika, T.; Iyoda, T.; Honda, K.; Shimidzu, T. J. Chem. Soc., Perkin Trans. 2 1993, 1181. (f) Newell, A. K.; Utley, J. H. P. J. Chem. Soc., Chem. Commun. 1992, 800. (g) Iyoda, T.; Saika, T.; Honda, K.; Shimidzu, T. Tetrahedron Lett. 1989, 30, 5429.
13. Handbook of Oligo- and Polythiophenes; Fichou, D., Ed.; Wiley-VHC: New York, 1999.
14. (b) Electronic Materials: The Oligomer Approach; Mullen, K., Wegner, G., Eds.; Wiley-VHC: New York, 1998.
15. Electrochemical cyclic voltammetry experiments were performed using a platinum disk working electrode, a platinum wire counter electrode, a Ag/AgCl (in a saturated NaCl solution) reference electrode, and tetrabutylammonium hexafluorophosphate (0.1 M) as the electrolyte. All results were referenced against ferrocene (0.40 V vs SCE). Electrolysis experiments were performed under similar conditions, except the platinum working electrode was replaced by a platinum coil.
16. 1H NMR spectroscopy. The ring-opening reactions were carried out using the light of a 150 W tungsten source that was passed through a 490 nm (for 1c, 2c, and 4c) or a 434 nm (for 3c and 5c) cutoff filter to eliminate higher energy light.
17. Identical results were obtained when the photostationary state (∼80% 1c) or purified samples (recrystallized from hexane) of 1c were used.
18. See Supporting Information for details.