메뉴 건너뛰기




Volumn 48, Issue 23, 2009, Pages 4185-4189

Linear π-acceptor-templated dynamic clipping to macrobicycles and [2]rotaxanes

Author keywords

interactions; Dynamic covalent chemistry; Rotaxanes; Self assembly; Template synthesis

Indexed keywords

BIPYRIDINIUM; CAGE FORMATION; DYNAMIC COVALENT CHEMISTRY; IMINE BONDS; MACROBICYCLE; ROTAXANES; SINGLE PRODUCT; SYMMETRY MISMATCH; TEMPLATE SYNTHESIS; TEMPLATED;

EID: 70349783528     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200900716     Document Type: Article
Times cited : (87)

References (93)
  • 3
    • 0003542983 scopus 로고    scopus 로고
    • Eds, J.-P. Sauvage, C. Dietrich-Buchecker, Wiley-VCH, Weinheim
    • c) Molecular Catenanes, Rotaxanes, and Knots (Eds.: J.-P. Sauvage, C. Dietrich-Buchecker), Wiley-VCH, Weinheim, 1999.
    • (1999) Molecular Catenanes, Rotaxanes, and Knots
  • 5
    • 0034596923 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2000, 39, 3348-3391;
    • (2000) Angew. Chem. Int. Ed , vol.39 , pp. 3348-3391
  • 11
  • 18
    • 22144436256 scopus 로고    scopus 로고
    • 1, see the Supporting Information
    • b) Y. Liu, et a1., J. Am. Chem. Soc. 2005, 127, 9745-9759; see the Supporting Information.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 9745-9759
    • Liu, Y.1    et a2
  • 24
    • 41049086346 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 2222-2226.
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 2222-2226
  • 26
    • 0003570337 scopus 로고    scopus 로고
    • Eds, F. Diederich, P. J. Stang, Wiley-VCH, Weinheim
    • b) Templated Organic Synthesis (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1999;
    • (1999) Templated Organic Synthesis
  • 28
    • 1242280982 scopus 로고
    • see the Supporting Information;
    • a) P. R. Anelli, et al., J. Am. Chem. Soc. 1992, 114, 193-218, see the Supporting Information;
    • (1992) J. Am. Chem. Soc , vol.114 , pp. 193-218
    • Anelli, P.R.1
  • 36
    • 0000671730 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2002, 41, 898-952;
    • (2002) Angew. Chem. Int. Ed , vol.41 , pp. 898-952
  • 41
    • 0035906693 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 1870-1875;
    • (2001) Angew. Chem. Int. Ed , vol.40 , pp. 1870-1875
  • 45
    • 33750211323 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 6665-6669;
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 6665-6669
  • 48
    • 33846035296 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 218-222.
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 218-222
  • 59
    • 0022017136 scopus 로고
    • a)J. M. Lehn, Science 1985, 227, 849-856;
    • (1985) Science , vol.227 , pp. 849-856
    • Lehn, J.M.1
  • 62
    • 0033549569 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 1999, 38, 1968-1971;
    • (1999) Angew. Chem. Int. Ed , vol.38 , pp. 1968-1971
  • 64
    • 36749065485 scopus 로고    scopus 로고
    • a)M. Mascal, Angew. Chem. 2006, 118, 2956-2959;
    • (2006) Angew. Chem , vol.118 , pp. 2956-2959
    • Mascal, M.1
  • 65
    • 33746191905 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 2890-2893;
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 2890-2893
  • 67
    • 36749056757 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 8782-8784.
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 8782-8784
  • 78
    • 0027209134 scopus 로고    scopus 로고
    • Templated synthesis of cryptands by a [2+3] clipping protocol was limited to only some N-bridgeheaded cryptands with spherical metal ions used as the templates, see a K. G. Ragunathan, R. Shukla, S. Mishra, P. K. Bharadwaj, Tetrahedron Lett. 1993, 34, 5631-5634;
    • Templated synthesis of cryptands by a [2+3] clipping protocol was limited to only some N-bridgeheaded cryptands with spherical metal ions used as the templates, see a) K. G. Ragunathan, R. Shukla, S. Mishra, P. K. Bharadwaj, Tetrahedron Lett. 1993, 34, 5631-5634;
  • 82
    • 70349957109 scopus 로고    scopus 로고
    • Although π donors and acceptors were widely used as kinetic templates in the synthesis of interlocked molecules, no π templates have been reported for rotaxane synthesis by using a dynamic clipping protocol
    • Although π donors and acceptors were widely used as kinetic templates in the synthesis of interlocked molecules, no π templates have been reported for rotaxane synthesis by using a dynamic clipping protocol.
  • 83
    • 70349962290 scopus 로고    scopus 로고
    • 3-symmetrical aromatic compounds were investigated as templates, but failed: mesitylene, 1,3,5-trihydroxyben-zene, 1,3,5-tris(4-pyridyl)benzene, and coronene.
    • 3-symmetrical aromatic compounds were investigated as templates, but failed: mesitylene, 1,3,5-trihydroxyben-zene, 1,3,5-tris(4-pyridyl)benzene, and coronene.
  • 84
    • 70349960594 scopus 로고    scopus 로고
    • Rigid macrobicyclic molecular cages based on metal-ligand coordination have been reported by Fujita and co-workers, see: a K. Kumazawa, K. Biradha, T. Kusukawa, T. Okano, M. Fujita, Angew. Chem. 2003, 115, 4039-4043;
    • Rigid macrobicyclic molecular cages based on metal-ligand coordination have been reported by Fujita and co-workers, see: a) K. Kumazawa, K. Biradha, T. Kusukawa, T. Okano, M. Fujita, Angew. Chem. 2003, 115, 4039-4043;
  • 85
    • 0041817633 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 3909-3913;
    • (2003) Angew. Chem. Int. Ed , vol.42 , pp. 3909-3913
  • 87
    • 17044434331 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 1810-1813;
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 1810-1813
  • 89
    • 70349963544 scopus 로고    scopus 로고
    • Although the 1H NMR spectra of 5(PF6)2 and 6(PF6)2 were recorded in different solvent systems because of solubility limitations, the large upfield shift of the H β resonance (0.7 ppm) cannot be accounted for by solvent effects alone, because only insignificant shifts (< 0.1 ppm) were observed for the resonances of aromatic protons (Hc, Hd, He, and Hf) on the stopper
    • f) on the stopper.
  • 90
    • 70349949642 scopus 로고    scopus 로고
    • 3. MOE2006 is a product of Chemical Computing Group, Montreal, Canada.
    • 3. MOE2006 is a product of Chemical Computing Group, Montreal, Canada.
  • 93
    • 70349962284 scopus 로고    scopus 로고
    • The high reactivity of bipyridinium towards common reductants posed a problem in our attempts to reduce the imine bonds in order to kinetically lock the [2]rotaxane. Whilst exploring other mild reducing agents, we are also searching for other π-acceptor-based templates, such as pyromellitic diimide, which is more compatible with the reducing conditions for the imine bonds
    • The high reactivity of bipyridinium towards common reductants posed a problem in our attempts to reduce the imine bonds in order to kinetically lock the [2]rotaxane. Whilst exploring other mild reducing agents, we are also searching for other π-acceptor-based templates, such as pyromellitic diimide, which is more compatible with the reducing conditions for the imine bonds.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.