메뉴 건너뛰기




Volumn 42, Issue 20, 2003, Pages 2296-2300

Remarkable positional discrimination in bistable light- and heat-switchable hydrogen-bonded molecular shuttles

Author keywords

Hydrogen bonds; Macrocycles; Molecular devices; Photochemistry; Rotaxanes

Indexed keywords

MOLECULAR BEAMS; THERMAL EFFECTS;

EID: 0037709923     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200250745     Document Type: Article
Times cited : (183)

References (38)
  • 2
    • 0034596923 scopus 로고    scopus 로고
    • For recent reviews see a) V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. 2000, 112, 3484-3530; Angew. Chem. Int. Ed. 2000, 39, 3349-3391;
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3349-3391
  • 5
  • 6
    • 33748245015 scopus 로고
    • A. C. Benniston, A. Harriman, Angew. Chem. 1993, 105, 1553- 1555; Angew. Chem. Int. Ed. Engl. 1993, 32, 1459-1461.
    • (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 1459-1461
  • 15
    • 0036260211 scopus 로고    scopus 로고
    • C. A. Stanier, S. J. Alderman, T. D. W. Claridge, H. L. Anderson, Angew. Chem. 2002, 114, 1847-1850; Angew. Chem. Int. Ed. 2002, 41, 1769-1772.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 1769-1772
  • 16
    • 0028276063 scopus 로고
    • For examples featuring the use of stimuli other than light to induce shuttling in rotaxanes see a) R. A. Bissell, E. Córdova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133-137; b) J. P. Collin, P. Gaviña, J. P. Sauvage, New J. Chem. 1997, 21, 525-528; c) C. Gong, H. W. Gibson, Angew. Chem. 1997, 109, 2426-2428; Angew. Chem. Int. Ed. Engl. 1997, 36, 2331-2333; d) A. S. Lane, D. A. Leigh, A. Murphy, J. Am. Chem. Soc. 1997, 119, 11092-11093; e) C. P. Collier, E. W. Wong, M. Belohradsky, F. M. Raymo, J. F. Stoddart, P. J. Kuekes, R. S. Williams, J. R. Heath, Science 1999, 285, 391-394; f) H. Shigekawa, K. Miyake, J. Sumaoka, A. Harada, M. Komiyama, J. Am. Chem. Soc. 2000, 122, 5411-5412; g) M.C. Jimenez-Molero, C. Dietrich-Buchecker, J. P. Sauvage, Chem. Eur. J. 2002, 8, 1456-1466; h) Y. Luo, C. P. Collier, J. O. Jeppesen, K. A. Nielsen, E. Delonno, G. Ho, J. Perkins, H. R. Tseng, T. Yamamoto, J. F. Stoddart, J. R. Heath, Chem Phys Chem 2002, 3, 519-525.
    • (1994) Nature , vol.369 , pp. 133-137
    • Bissell, R.A.1    Córdova, E.2    Kaifer, A.E.3    Stoddart, J.F.4
  • 17
    • 0006691651 scopus 로고    scopus 로고
    • For examples featuring the use of stimuli other than light to induce shuttling in rotaxanes see a) R. A. Bissell, E. Córdova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133-137; b) J. P. Collin, P. Gaviña, J. P. Sauvage, New J. Chem. 1997, 21, 525-528; c) C. Gong, H. W. Gibson, Angew. Chem. 1997, 109, 2426-2428; Angew. Chem. Int. Ed. Engl. 1997, 36, 2331-2333; d) A. S. Lane, D. A. Leigh, A. Murphy, J. Am. Chem. Soc. 1997, 119, 11092-11093; e) C. P. Collier, E. W. Wong, M. Belohradsky, F. M. Raymo, J. F. Stoddart, P. J. Kuekes, R. S. Williams, J. R. Heath, Science 1999, 285, 391-394; f) H. Shigekawa, K. Miyake, J. Sumaoka, A. Harada, M. Komiyama, J. Am. Chem. Soc. 2000, 122, 5411-5412; g) M.C. Jimenez-Molero, C. Dietrich-Buchecker, J. P. Sauvage, Chem. Eur. J. 2002, 8, 1456-1466; h) Y. Luo, C. P. Collier, J. O. Jeppesen, K. A. Nielsen, E. Delonno, G. Ho, J. Perkins, H. R. Tseng, T. Yamamoto, J. F. Stoddart, J. R. Heath, Chem Phys Chem 2002, 3, 519-525.
    • (1997) Chem , vol.21 , pp. 525-528
    • Collin, J.P.1    Gaviña, P.2    Sauvage, J.P.3    New, J.4
  • 18
    • 0000843477 scopus 로고    scopus 로고
    • For examples featuring the use of stimuli other than light to induce shuttling in rotaxanes see a) R. A. Bissell, E. Córdova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133-137; b) J. P. Collin, P. Gaviña, J. P. Sauvage, New J. Chem. 1997, 21, 525-528; c) C. Gong, H. W. Gibson, Angew. Chem. 1997, 109, 2426-2428; Angew. Chem. Int. Ed. Engl. 1997, 36, 2331-2333; d) A. S. Lane, D. A. Leigh, A. Murphy, J. Am. Chem. Soc. 1997, 119, 11092-11093; e) C. P. Collier, E. W. Wong, M. Belohradsky, F. M. Raymo, J. F. Stoddart, P. J. Kuekes, R. S. Williams, J. R. Heath, Science 1999, 285, 391-394; f) H. Shigekawa, K. Miyake, J. Sumaoka, A. Harada, M. Komiyama, J. Am. Chem. Soc. 2000, 122, 5411-5412; g) M.C. Jimenez-Molero, C. Dietrich-Buchecker, J. P. Sauvage, Chem. Eur. J. 2002, 8, 1456-1466; h) Y. Luo, C. P. Collier, J. O. Jeppesen, K. A. Nielsen, E. Delonno, G. Ho, J. Perkins, H. R. Tseng, T. Yamamoto, J. F. Stoddart, J. R. Heath, Chem Phys Chem 2002, 3, 519-525.
    • (1997) Angew. Chem. , vol.109 , pp. 2426-2428
    • Gong, C.1    Gibson, H.W.2
  • 19
    • 0030678039 scopus 로고    scopus 로고
    • For examples featuring the use of stimuli other than light to induce shuttling in rotaxanes see a) R. A. Bissell, E. Córdova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133-137; b) J. P. Collin, P. Gaviña, J. P. Sauvage, New J. Chem. 1997, 21, 525-528; c) C. Gong, H. W. Gibson, Angew. Chem. 1997, 109, 2426-2428; Angew. Chem. Int. Ed. Engl. 1997, 36, 2331-2333; d) A. S. Lane, D. A. Leigh, A. Murphy, J. Am. Chem. Soc. 1997, 119, 11092-11093; e) C. P. Collier, E. W. Wong, M. Belohradsky, F. M. Raymo, J. F. Stoddart, P. J. Kuekes, R. S. Williams, J. R. Heath, Science 1999, 285, 391-394; f) H. Shigekawa, K. Miyake, J. Sumaoka, A. Harada, M. Komiyama, J. Am. Chem. Soc. 2000, 122, 5411-5412; g) M.C. Jimenez-Molero, C. Dietrich-Buchecker, J. P. Sauvage, Chem. Eur. J. 2002, 8, 1456-1466; h) Y. Luo, C. P. Collier, J. O. Jeppesen, K. A. Nielsen, E. Delonno, G. Ho, J. Perkins, H. R. Tseng, T. Yamamoto, J. F. Stoddart, J. R. Heath, Chem Phys Chem 2002, 3, 519-525.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 2331-2333
  • 20
    • 0030691058 scopus 로고    scopus 로고
    • For examples featuring the use of stimuli other than light to induce shuttling in rotaxanes see a) R. A. Bissell, E. Córdova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133-137; b) J. P. Collin, P. Gaviña, J. P. Sauvage, New J. Chem. 1997, 21, 525-528; c) C. Gong, H. W. Gibson, Angew. Chem. 1997, 109, 2426-2428; Angew. Chem. Int. Ed. Engl. 1997, 36, 2331-2333; d) A. S. Lane, D. A. Leigh, A. Murphy, J. Am. Chem. Soc. 1997, 119, 11092-11093; e) C. P. Collier, E. W. Wong, M. Belohradsky, F. M. Raymo, J. F. Stoddart, P. J. Kuekes, R. S. Williams, J. R. Heath, Science 1999, 285, 391-394; f) H. Shigekawa, K. Miyake, J. Sumaoka, A. Harada, M. Komiyama, J. Am. Chem. Soc. 2000, 122, 5411-5412; g) M.C. Jimenez-Molero, C. Dietrich-Buchecker, J. P. Sauvage, Chem. Eur. J. 2002, 8, 1456-1466; h) Y. Luo, C. P. Collier, J. O. Jeppesen, K. A. Nielsen, E. Delonno, G. Ho, J. Perkins, H. R. Tseng, T. Yamamoto, J. F. Stoddart, J. R. Heath, Chem Phys Chem 2002, 3, 519-525.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 11092-11093
    • Lane, A.S.1    Leigh, D.A.2    Murphy, A.3
  • 21
    • 0033575366 scopus 로고    scopus 로고
    • For examples featuring the use of stimuli other than light to induce shuttling in rotaxanes see a) R. A. Bissell, E. Córdova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133-137; b) J. P. Collin, P. Gaviña, J. P. Sauvage, New J. Chem. 1997, 21, 525-528; c) C. Gong, H. W. Gibson, Angew. Chem. 1997, 109, 2426-2428; Angew. Chem. Int. Ed. Engl. 1997, 36, 2331-2333; d) A. S. Lane, D. A. Leigh, A. Murphy, J. Am. Chem. Soc. 1997, 119, 11092-11093; e) C. P. Collier, E. W. Wong, M. Belohradsky, F. M. Raymo, J. F. Stoddart, P. J. Kuekes, R. S. Williams, J. R. Heath, Science 1999, 285, 391-394; f) H. Shigekawa, K. Miyake, J. Sumaoka, A. Harada, M. Komiyama, J. Am. Chem. Soc. 2000, 122, 5411-5412; g) M.C. Jimenez-Molero, C. Dietrich-Buchecker, J. P. Sauvage, Chem. Eur. J. 2002, 8, 1456-1466; h) Y. Luo, C. P. Collier, J. O. Jeppesen, K. A. Nielsen, E. Delonno, G. Ho, J. Perkins, H. R. Tseng, T. Yamamoto, J. F. Stoddart, J. R. Heath, Chem Phys Chem 2002, 3, 519-525.
    • (1999) Science , vol.285 , pp. 391-394
    • Collier, C.P.1    Wong, E.W.2    Belohradsky, M.3    Raymo, F.M.4    Stoddart, J.F.5    Kuekes, P.J.6    Williams, R.S.7    Heath, J.R.8
  • 22
    • 0034616875 scopus 로고    scopus 로고
    • For examples featuring the use of stimuli other than light to induce shuttling in rotaxanes see a) R. A. Bissell, E. Córdova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133-137; b) J. P. Collin, P. Gaviña, J. P. Sauvage, New J. Chem. 1997, 21, 525-528; c) C. Gong, H. W. Gibson, Angew. Chem. 1997, 109, 2426-2428; Angew. Chem. Int. Ed. Engl. 1997, 36, 2331-2333; d) A. S. Lane, D. A. Leigh, A. Murphy, J. Am. Chem. Soc. 1997, 119, 11092-11093; e) C. P. Collier, E. W. Wong, M. Belohradsky, F. M. Raymo, J. F. Stoddart, P. J. Kuekes, R. S. Williams, J. R. Heath, Science 1999, 285, 391-394; f) H. Shigekawa, K. Miyake, J. Sumaoka, A. Harada, M. Komiyama, J. Am. Chem. Soc. 2000, 122, 5411-5412; g) M.C. Jimenez-Molero, C. Dietrich-Buchecker, J. P. Sauvage, Chem. Eur. J. 2002, 8, 1456-1466; h) Y. Luo, C. P. Collier, J. O. Jeppesen, K. A. Nielsen, E. Delonno, G. Ho, J. Perkins, H. R. Tseng, T. Yamamoto, J. F. Stoddart, J. R. Heath, Chem Phys Chem 2002, 3, 519-525.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 5411-5412
    • Shigekawa, H.1    Miyake, K.2    Sumaoka, J.3    Harada, A.4    Komiyama, M.5
  • 23
    • 0037087495 scopus 로고    scopus 로고
    • For examples featuring the use of stimuli other than light to induce shuttling in rotaxanes see a) R. A. Bissell, E. Córdova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133-137; b) J. P. Collin, P. Gaviña, J. P. Sauvage, New J. Chem. 1997, 21, 525-528; c) C. Gong, H. W. Gibson, Angew. Chem. 1997, 109, 2426-2428; Angew. Chem. Int. Ed. Engl. 1997, 36, 2331-2333; d) A. S. Lane, D. A. Leigh, A. Murphy, J. Am. Chem. Soc. 1997, 119, 11092-11093; e) C. P. Collier, E. W. Wong, M. Belohradsky, F. M. Raymo, J. F. Stoddart, P. J. Kuekes, R. S. Williams, J. R. Heath, Science 1999, 285, 391-394; f) H. Shigekawa, K. Miyake, J. Sumaoka, A. Harada, M. Komiyama, J. Am. Chem. Soc. 2000, 122, 5411-5412; g) M.C. Jimenez-Molero, C. Dietrich-Buchecker, J. P. Sauvage, Chem. Eur. J. 2002, 8, 1456-1466; h) Y. Luo, C. P. Collier, J. O. Jeppesen, K. A. Nielsen, E. Delonno, G. Ho, J. Perkins, H. R. Tseng, T. Yamamoto, J. F. Stoddart, J. R. Heath, Chem Phys Chem 2002, 3, 519-525.
    • (2002) Chem. Eur. J. , vol.8 , pp. 1456-1466
    • Jimenez-Molero, M.C.1    Dietrich-Buchecker, C.2    Sauvage, J.P.3
  • 24
    • 0037124873 scopus 로고    scopus 로고
    • For examples featuring the use of stimuli other than light to induce shuttling in rotaxanes see a) R. A. Bissell, E. Córdova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133-137; b) J. P. Collin, P. Gaviña, J. P. Sauvage, New J. Chem. 1997, 21, 525-528; c) C. Gong, H. W. Gibson, Angew. Chem. 1997, 109, 2426-2428; Angew. Chem. Int. Ed. Engl. 1997, 36, 2331-2333; d) A. S. Lane, D. A. Leigh, A. Murphy, J. Am. Chem. Soc. 1997, 119, 11092-11093; e) C. P. Collier, E. W. Wong, M. Belohradsky, F. M. Raymo, J. F. Stoddart, P. J. Kuekes, R. S. Williams, J. R. Heath, Science 1999, 285, 391-394; f) H. Shigekawa, K. Miyake, J. Sumaoka, A. Harada, M. Komiyama, J. Am. Chem. Soc. 2000, 122, 5411-5412; g) M.C. Jimenez-Molero, C. Dietrich-Buchecker, J. P. Sauvage, Chem. Eur. J. 2002, 8, 1456-1466; h) Y. Luo, C. P. Collier, J. O. Jeppesen, K. A. Nielsen, E. Delonno, G. Ho, J. Perkins, H. R. Tseng, T. Yamamoto, J. F. Stoddart, J. R. Heath, Chem Phys Chem 2002, 3, 519-525.
    • (2002) ChemPhysChem. , vol.3 , pp. 519-525
    • Luo, Y.1    Collier, C.P.2    Jeppesen, J.O.3    Nielsen, K.A.4    Delonno, E.5    Ho, G.6    Perkins, J.7    Tseng, H.R.8    Yamamoto, T.9    Stoddart, J.F.10    Heath, J.R.11
  • 28
    • 0038764968 scopus 로고    scopus 로고
    • note
    • 2 at 233 K.
  • 32
    • 0038088328 scopus 로고    scopus 로고
    • note
    • 6]DMSO the fumaramide station is still occupied by the macrocycle for at least 85% of the time.
  • 33
    • 0000802654 scopus 로고
    • The yield of the adipamide-maleamide rotaxane Z-3 (20%) is reproducibly higher than that of the model single-site adipamide rotaxane shown in Figure 2 (8%). The significant differences in yield (and the anomalously poor binding of the adipamide unit to the macrocycle in Z-3) may indicate that the intramolecularly hydrogen-bonded nine-membered ring (S. H. Gellman, G. P. Dado, G.-B. Liang, B. R. Adams, J. Am. Chem. Soc. 1991, 113, 1164-1173) has differing stabilities in the one- and two-station adipamide threads and rotaxane Z-3.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 1164-1173
    • Gellman, S.H.1    Dado, G.P.2    Liang, G.-B.3    Adams, B.R.4
  • 37
    • 0037750690 scopus 로고    scopus 로고
    • note
    • -1; equilibrium H-bonding separation: 2.78 Å).
  • 38
    • 0038427019 scopus 로고    scopus 로고
    • note
    • The rotaxane structures shown illustrate the position of the macrocycle on the thread and particularly favored intercomponent hydrogen-bonding motifs. Most of the low-energy coconformations of the rotaxanes are probably folded with the unoccupied station folding back to hydrogen bond to the macrocycle.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.