메뉴 건너뛰기




Volumn 72, Issue 4, 2007, Pages 1073-1087

Synthesis and structural and photoswitchable properties of novel chiral host molecules: Axis chiral 2,2′-dihydroxy-1,1′-binaphthyl-appended stiff-stilbene

Author keywords

[No Author keywords available]

Indexed keywords

BIOSYNTHESIS; CATALYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL PROPERTIES; PALLADIUM;

EID: 33846991662     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061127v     Document Type: Article
Times cited : (51)

References (72)
  • 1
    • 33846981748 scopus 로고    scopus 로고
    • Photoswitchable Host Molecules. 1.
    • Photoswitchable Host Molecules. 1.
  • 2
    • 0004240038 scopus 로고    scopus 로고
    • For reviews on molecular motors using the isomerization of double bonds, see: a, Wiley-VCH: New York, Chapter 5
    • For reviews on molecular motors using the isomerization of double bonds, see: (a) Feringa, B. L. Molecular Switches; Wiley-VCH: New York, 2003; Chapter 5.
    • (2003) Molecular Switches
    • Feringa, B.L.1
  • 8
    • 0012317549 scopus 로고    scopus 로고
    • For reviews on molecular switches using the isomerization of double bonds, see: a, Wiley-VCH: New York, Chapters 4 and 7
    • For reviews on molecular switches using the isomerization of double bonds, see: (a) Journey, A.; Credi, A.; Venturi, M. Molecular Devices and Machines; Wiley-VCH: New York, 2004; Chapters 4 and 7.
    • (2004) Molecular Devices and Machines
    • Journey, A.1    Credi, A.2    Venturi, M.3
  • 10
    • 0004240038 scopus 로고    scopus 로고
    • For reviews on molecular machines using the isomerization of double bonds, see: a, Wiley-VCH: New York, Chapters 7 and 9
    • For reviews on molecular machines using the isomerization of double bonds, see: (a) Feringa, B. L. Molecular Switches; Wiley-VCH: New York, 2003; Chapters 7 and 9.
    • (2003) Molecular Switches
    • Feringa, B.L.1
  • 15
    • 27844551189 scopus 로고    scopus 로고
    • Molecular machines using the isomerization of double bonds: (f) Murakami, H.; Kawabuchi, A.; Matsumoto, R.; Ho, T.; Nakashima, N. J. Am. Chem. Soc. 2005, 127, 15891-15899.
    • Molecular machines using the isomerization of double bonds: (f) Murakami, H.; Kawabuchi, A.; Matsumoto, R.; Ho, T.; Nakashima, N. J. Am. Chem. Soc. 2005, 127, 15891-15899.
  • 22
    • 33846976927 scopus 로고    scopus 로고
    • For an example of the geometry of stiff-stilbene, see: (a) Schaefer, W. P. Acta Crystallogr., Sect C 1995, C51, 2364-2366.
    • For an example of the geometry of stiff-stilbene, see: (a) Schaefer, W. P. Acta Crystallogr., Sect C 1995, C51, 2364-2366.
  • 26
    • 0010807072 scopus 로고    scopus 로고
    • For an example of the photophysics of a stiff-stilbene analogue, see: (f) Ogawa, K.; Suzuki, H.; Futakami, M. J. Chem. Soc., Perkin trans. 2 1988, 39-43.
    • For an example of the photophysics of a stiff-stilbene analogue, see: (f) Ogawa, K.; Suzuki, H.; Futakami, M. J. Chem. Soc., Perkin trans. 2 1988, 39-43.
  • 52
    • 4243973410 scopus 로고
    • (a) McMurry, J. E. Chem. Rev. 1989, 89, 1513-1524.
    • (1989) Chem. Rev , vol.89 , pp. 1513-1524
    • McMurry, J.E.1
  • 54
    • 20544433165 scopus 로고
    • (a) Bondi, A. Phys. Chem. 1964, 68, 441-451.
    • (1964) Phys. Chem , vol.68 , pp. 441-451
    • Bondi, A.1
  • 57
    • 33846969423 scopus 로고    scopus 로고
    • 1H COSY measurement, see: Braun, S.; Kalinowski, H.-O.; Berger, S. 150 and More Basic NMR Experiments A Practical Course, 2nd expanded ed.; Wiley-VCH: New York, 1998; Chapter 10, Experiment 10.3.
    • 1H COSY measurement, see: Braun, S.; Kalinowski, H.-O.; Berger, S. 150 and More Basic NMR Experiments A Practical Course, 2nd expanded ed.; Wiley-VCH: New York, 1998; Chapter 10, Experiment 10.3.
  • 60
    • 33846958639 scopus 로고    scopus 로고
    • For an example of the DPFGSE (double pulsed field gradient spin echo) method-NOE, see: Braun, S.; Kalinowski, H.-O.; Berger, S. 150 and More Basic NMR Experiments A Practical Course, 2nd expanded ed.; Wiley-VCH: New York, 1998; Chapter 11, Experiment 11.10.
    • For an example of the DPFGSE (double pulsed field gradient spin echo) method-NOE, see: Braun, S.; Kalinowski, H.-O.; Berger, S. 150 and More Basic NMR Experiments A Practical Course, 2nd expanded ed.; Wiley-VCH: New York, 1998; Chapter 11, Experiment 11.10.
  • 61
    • 0000897825 scopus 로고
    • For an example of the assignment of transition bands in BINOL, see: a
    • For an example of the assignment of transition bands in BINOL, see: (a) Hanazaki, I.; Akimoto, H. J. Am. Chem. Soc. 1972, 94, 4102-4106.
    • (1972) J. Am. Chem. Soc , vol.94 , pp. 4102-4106
    • Hanazaki, I.1    Akimoto, H.2
  • 64
    • 33847000432 scopus 로고    scopus 로고
    • We compared the rate of the cis-trans photochemical isomerization of trans-(R,R)-1 with azobenzene upon irradiation with 365 and ca. 410 nm light at 23°C in benzene, and the reactions were monitored by 1H NMR spectra. The photoisomerization of trans-(R,R)-1 to cis-(R,R)-1 reached 86/14 (cis/trans) after 60 min of irradiation and was ca. 2.3 times faster than that of azobenzene (84/16 after 140 min of irradiation, On the other hand, the rate of photochemical isomerization from cis-(R,R)-1 to trans-(R,R)-1 (23/77 after 20 min) was almost similar to that of azobenzene (22/78 after 20 min) in benzene. Comparison of the rates of trans to cis photoisomerization between 1 and azobenzene in benzene and those of the reverse isomerization are summarized in Figures S23 and S24, respectively. For the rates of isomerization of azobenzene, see: Yamashita, S, Ono, H, Toyama, O
    • 1H NMR spectra. The photoisomerization of trans-(R,R)-1 to cis-(R,R)-1 reached 86/14 (cis/trans) after 60 min of irradiation and was ca. 2.3 times faster than that of azobenzene (84/16 after 140 min of irradiation). On the other hand, the rate of photochemical isomerization from cis-(R,R)-1 to trans-(R,R)-1 (23/77 after 20 min) was almost similar to that of azobenzene (22/78 after 20 min) in benzene. Comparison of the rates of trans to cis photoisomerization between 1 and azobenzene in benzene and those of the reverse isomerization are summarized in Figures S23 and S24, respectively. For the rates of isomerization of azobenzene, see: Yamashita, S.; Ono, H.; Toyama, O. Bull. Chem. Soc. Jpn. 1962, 35, 1849-1853.
  • 65
    • 84890990283 scopus 로고    scopus 로고
    • For examples of NH-based anion receptors, see: Schrader, T, Hamilton, A. D. Functional Synthetic Receptors; Wiley-VCH: New York, 2005; Chapter 4
    • For examples of NH-based anion receptors, see: Schrader, T.; Hamilton, A. D. Functional Synthetic Receptors; Wiley-VCH: New York, 2005; Chapter 4.
  • 69
    • 33846996690 scopus 로고    scopus 로고
    • 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, Millam, J. M, Iyengar, S. S, Tomasi, J, Barone, V, Mennucci, B, Cossi, M, Scalmani, G, Rega, N, Petersson, G. A, Nakatsuji, H, Hada, M, Ehara, M, Toyota, K, Fukuda, R, Hasegawa, J, Ishida, M, Nakajima, T, Honda, Y, Kitao, O, Nakai, H, Klene, M, Li, X, knox, J. E, Hratchian, H. P, Cross, J. B, Bakken, V, Adamo, C, Jaramillo, J, Gomperts, R, Stratmann, R. E, Yazyev, O, Austin, A. J, Cammi, R, Pomelli, C, Ochterski, J. W, Ayala, P. Y, Morokuma, K, Voth, G. A, Salvador, P, Dannenberg, J. J, Zakrzewski, V. G, Dapprich, S, Daniels, A. D, Strain, M. C, Farkas, O, Malick, D. K, Rabuck, A. D, Raghavachari, K, Foresman, J. B, Ortiz, J. V, Cui, Q, Baboul, A. G, Clifford, S, Cioslowski, J, Stefanov, B. B, Liu, G, Liashenko, A, Piskorz, P, komaromi, I, Martin, R. L, Fox, D. J, Keit
    • 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.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Lahm, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzales, C.; Pople, J. A. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.