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Volumn 26, Issue 20, 2007, Pages 5030-5041

Preparation and photochemical behavior of organoruthenium derivatives of photochromic dithienylethene (DTE):

Author keywords

[No Author keywords available]

Indexed keywords

MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; PHOTOCHEMICAL REACTIONS; PHOTOCHROMISM; X RAY CRYSTALLOGRAPHY;

EID: 34948911670     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om700537s     Document Type: Article
Times cited : (37)

References (100)
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    • The special thematic issue of Chem. Rev. for "Photochromism: Memories and Switches-Introduction", Chem. Rev. 2000, 100, 1683-1890.
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    • Organic Photochromic and Thermochromic Compounds; Crano, J. C., Guglielmetti, R. J., Eds.; Main Photochromic Families; Plenum Press: New York, 1999; 1.
    • Organic Photochromic and Thermochromic Compounds; Crano, J. C., Guglielmetti, R. J., Eds.; Main Photochromic Families; Plenum Press: New York, 1999; Vol. 1.
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    • Irie, M.1
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    • Spirobenzopyrane complexes: ref 6a. Miyashita, A.; Iwamoto, A.; Kuwayama, T.; Shitara, H.; Aoki, Y.; Hirano, M.; Nohira, H. Chem. Lett. 1997, 965.
    • Spirobenzopyrane complexes: ref 6a. Miyashita, A.; Iwamoto, A.; Kuwayama, T.; Shitara, H.; Aoki, Y.; Hirano, M.; Nohira, H. Chem. Lett. 1997, 965.
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    • Dihydropyrene complexes: Mitchell, R. H.; Brkic, Z.; Sauro, V. A.; Berg, D. J. J. Am. Chem. Soc. 2003, 125, 7581.
    • Dihydropyrene complexes: Mitchell, R. H.; Brkic, Z.; Sauro, V. A.; Berg, D. J. J. Am. Chem. Soc. 2003, 125, 7581.
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    • -3. Current R value = 0.20. An ORTEP view is shown in Figure S6.
    • -3. Current R value = 0.20. An ORTEP view is shown in Figure S6.
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    • Powell, P. J. Organomet. Chem. 1974, 65, 89. See also ref 10.
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    • 12) The related η5-C5R5-type Rh complex 26 was also prepared following the procedures reported for the η5-C5Me5 derivative (Kang, J. W, Moseley, K, Maitlis, P. M. J. Am. Chem. Soc. 1969, 91, 5970, Successive treatment of 20 with RhCl3·3H2O (in refluxing methanol) and PPh3 (in diethyl ether at r.t, gave 26 as red powder, which was characterized spectroscopically. In a manner similar to 12 and 13, UV light irradiation of 26 caused appearance of a weak UV-vis shoulder band around 600 nm, which disappeared upon subsequent visible light irradiation (Figure S8, while no apparent change was detected by 1H NMR. 26: δH(CDCl3) 7.60 (14H, br, Ph, 7.35 (8H, br, Ph, 7.23 (8H, br, Ph, 7.11 (2H, s, Th, 2.08 (6H, s, Me-Th, 1.54 (12H, d, J, 4.6, C5Me4, 1.37 12H, d, J, 2.7, C
    • -1): 419, 280 nm.
  • 62
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    • Preparation of a less sterically hindered indenyl derivative was attempted as shown below but unsuccessful. Via route 1, the desired product was formed but could not be separated from a mixture containing the monoindenyl compound and the starting compound. For route 2, although the intermediate corresponding to 17 could be obtained, subsequent lithiation with n-BuLi was followed by proton-transfer to give the debrominated product, as confirmed by D2O quenching. The less acidic C5Me4-H proton in 17 was resistant to the proton transfer, and therefore, 20 was obtained successfully. Image presented
    • 4-H proton in 17 was resistant to the proton transfer, and therefore, 20 was obtained successfully. Image presented.
  • 68
    • 34948855024 scopus 로고    scopus 로고
    • Because the thiophene part may participate in the reaction with Ru 3(CO)12, a preliminary experiment using a simpler thiophene-containing substrate was carried out and the expected product was obtained successfully and characterized spectroscopically (δH (CDCl3) 6.99, 6.72 (2H × 2, m × 2, Th, 2.49 (6H, s, Me-Th, 1.95, 1.77 (12H × 2, s × 2, C5Me4, IR (CH2Cl2) 1932, 1763 cm-1, But attempted preparation of the Cp*RuCl-(PPh3)2-type complex by successive treatment of the simpler thiophene with RuCl3· nH2O (in refluxing EtOH) and PPh3 resulted in the formation of a small amount of unidentified products. Image presented
    • 3 resulted in the formation of a small amount of unidentified products. Image presented
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    • - salt: Gemel, G.; Mereiter, K.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 532. See also ref 7.
    • - salt: Gemel, G.; Mereiter, K.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 532. See also ref 7.
  • 80
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    • 1H NMR sample of a higher concentration, light does not transmit the sample completely to make the photochemical process less efficient.
    • 1H NMR sample of a higher concentration, light does not transmit the sample completely to make the photochemical process less efficient.
  • 82
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    • 6 was used as the solvent
    • 6 was used as the solvent.
  • 84
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    • See ref 8. See also: Dougan, S. J.; Melchart, M.; Habtemariam, A.; Parsons, S.; Sadler, P. J. Inorg. Chem. 2006, 45, 10882.
    • See ref 8. See also: Dougan, S. J.; Melchart, M.; Habtemariam, A.; Parsons, S.; Sadler, P. J. Inorg. Chem. 2006, 45, 10882.
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    • teXsan: Crystal Structure Analysis Package, ver. 1. 11; Rigaku Corp.: Tokyo, Japan, 2000.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.