메뉴 건너뛰기




Volumn 5, Issue 8, 2013, Pages 704-710

A pentagonal cyanostar macrocycle with cyanostilbene CH donors binds anions and forms dialkylphosphate [3]rotaxanes

Author keywords

[No Author keywords available]

Indexed keywords

ANION; MACROCYCLIC COMPOUND; ROTAXANE; STILBENE DERIVATIVE;

EID: 84881097781     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.1668     Document Type: Article
Times cited : (308)

References (53)
  • 1
    • 0041127939 scopus 로고
    • Cyclic polyethers and their complexes with metal salts
    • Pedersen, C. J. Cyclic polyethers and their complexes with metal salts. J. Am. Chem. Soc. 89, 2495-2496 (1967).
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 2495-2496
    • Pedersen, C.J.1
  • 2
    • 0031191655 scopus 로고    scopus 로고
    • Signaling recognition events with fluorescent sensors and switches
    • de Silva, A. P. et al. Signaling recognition events with fluorescent sensors and switches. Chem. Rev. 97, 1515-1566 (1997).
    • (1997) Chem. Rev. , vol.97 , pp. 1515-1566
    • De Silva, A.P.1
  • 3
    • 37049104245 scopus 로고
    • Chiral crown complexes catalyse Michael addition reactions to give adducts in high optical yields
    • Cram, D. J. & Sogah, G. D. Y. Chiral crown complexes catalyse Michael addition reactions to give adducts in high optical yields. J. Chem. Soc. Chem. Commun. 625-628 (1981).
    • (1981) J. Chem. Soc. Chem. Commun. , pp. 625-628
    • Cram, D.J.1    Sogah, G.D.Y.2
  • 4
    • 84862527435 scopus 로고    scopus 로고
    • Acyclic cucurbit[n]uril molecular containers enhance the solubility and bioactivity of poorly soluble pharmaceuticals
    • Ma, D. et al. Acyclic cucurbit[n]uril molecular containers enhance the solubility and bioactivity of poorly soluble pharmaceuticals. Nature Chem. 4, 503-510 (2012).
    • (2012) Nature Chem. , vol.4 , pp. 503-510
    • Ma, D.1
  • 5
    • 69249147929 scopus 로고    scopus 로고
    • The chemistry of the mechanical bond
    • Stoddart, J. F. The chemistry of the mechanical bond. Chem. Soc. Rev. 38, 1802-1820 (2009).
    • (2009) Chem. Soc. Rev. , vol.38 , pp. 1802-1820
    • Stoddart, J.F.1
  • 6
    • 33846152351 scopus 로고    scopus 로고
    • Synthetic molecular motors and mechanical machines
    • Kay, E. R., Leigh, D. A. & Zerbetto, F. Synthetic molecular motors and mechanical machines. Angew. Chem. Int. Ed. 46, 72-191 (2007).
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 72-191
    • Kay, E.R.1    Leigh, D.A.2    Zerbetto, F.3
  • 7
    • 21244456892 scopus 로고    scopus 로고
    • Shape-persistent phenylene-acetylene macrocycles: Large rings-low yield?
    • Höger, S. Shape-persistent phenylene-acetylene macrocycles: Large rings-low yield? Angew. Chem. Int. Ed. 44, 3806-3808 (2005).
    • (2005) Angew Chem. Int. Ed. , vol.44 , pp. 3806-3808
    • Höger, S.1
  • 8
    • 0000612273 scopus 로고
    • The significance of complexes of macrocyclic ligands and their synthesis by ligand reactions
    • Busch, D. H. The significance of complexes of macrocyclic ligands and their synthesis by ligand reactions. Rec. Chem. Progr. 25, 107-126 (1964).
    • (1964) Rec. Chem. Progr. , vol.25 , pp. 107-126
    • Busch, D.H.1
  • 9
    • 42149123240 scopus 로고    scopus 로고
    • Para-Bridged symmetrical pillar arenes: Their Lewis acid catalyzed synthesis and host-guest property
    • Ogoshi, T., Kanai, S., Fujinami, S., Yamagishi, T. & Nakamoto, Y. para-Bridged symmetrical pillar arenes: Their Lewis acid catalyzed synthesis and host-guest property. J. Am. Chem. Soc. 130, 5022-5023 (2008).
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 5022-5023
    • Ogoshi, T.1    Kanai, S.2    Fujinami, S.3    Yamagishi, T.4    Nakamoto, Y.5
  • 10
    • 4544301723 scopus 로고    scopus 로고
    • Highly efficient, one-step macrocyclizations assisted by the folding and preorganization of precursor oligomers
    • Yuan, L. H. et al. Highly efficient, one-step macrocyclizations assisted by the folding and preorganization of precursor oligomers. J. Am. Chem. Soc. 126, 11120-11121 (2004).
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 11120-11121
    • Yuan, L.H.1
  • 11
    • 5644250509 scopus 로고    scopus 로고
    • Arylene ethynylene macrocycles prepared by precipitation-driven alkyne metathesis
    • Zhang, W. & Moore, J. S. Arylene ethynylene macrocycles prepared by precipitation-driven alkyne metathesis. J. Am. Chem. Soc., 126, 12796 (2004).
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 12796
    • Zhang, W.1    Moore, J.S.2
  • 12
    • 77949818761 scopus 로고    scopus 로고
    • Click chemistry generates privileged CH hydrogenbonding triazoles: The latest addition to anion supramolecular chemistry
    • Hua, Y. & Flood, A. H. Click chemistry generates privileged CH hydrogenbonding triazoles: The latest addition to anion supramolecular chemistry. Chem. Soc. Rev. 39, 1262-1271 (2010).
    • (2010) Chem. Soc. Rev. , vol.39 , pp. 1262-1271
    • Hua, Y.1    Flood, A.H.2
  • 13
    • 20444434683 scopus 로고    scopus 로고
    • Are C-H groups significant hydrogen bonding sites in anion receptors? Benzene complexes with Cl2 NO3 and ClO4 2
    • Bryantsev, V. S. & Hay, B. P. Are C-H groups significant hydrogen bonding sites in anion receptors? Benzene complexes with Cl2, NO3 and ClO4 2. J. Am. Chem. Soc. 127, 8282-8283 (2005).
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 8282-8283
    • Bryantsev, V.S.1    Hay, B.P.2
  • 14
    • 41949128097 scopus 로고    scopus 로고
    • Pure C-H hydrogen bonding to chloride ions: A preorganized and rigid macrocyclic receptor
    • Li, Y. & Flood, A. H. Pure C-H hydrogen bonding to chloride ions: A preorganized and rigid macrocyclic receptor. Angew. Chem. Int. Ed. 47, 2649-2652 (2008).
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 2649-2652
    • Li, Y.1    Flood, A.H.2
  • 15
    • 77957699356 scopus 로고    scopus 로고
    • A pyrrolyl-based triazolophane: A macrocyclic receptor with CH and NH donor groups that exhibits a preference for pyrophosphate anions
    • Sessler, J. L. et al. A pyrrolyl-based triazolophane: A macrocyclic receptor with CH and NH donor groups that exhibits a preference for pyrophosphate anions. J. Am. Chem. Soc. 132, 14058-14060 (2010).
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 14058-14060
    • Sessler, J.L.1
  • 16
    • 84984268284 scopus 로고
    • Structural study of stilbenes 2 Crystal-structure redetermination of trans-4′-dimethylamino-4-nitro-a-cyanostilbene C17H15N3O2
    • Tinant, B. et al. Structural study of stilbenes. 2. Crystal-structure redetermination of trans-4′-dimethylamino-4-nitro-a-cyanostilbene C17H15N3O2. Bull. Soc. Chim. Belg. 92, 403-404 (1983).
    • (1983) Bull. Soc. Chim. Belg. , vol.92 , pp. 403-404
    • Tinant, B.1
  • 17
    • 1442310091 scopus 로고
    • Charge separation and photovoltaic conversion in polymer composites with internal donor-acceptor heterojunctions
    • Yu, G. & Heeger, A. J. Charge separation and photovoltaic conversion in polymer composites with internal donor-acceptor heterojunctions. J. Appl. Phys. 78, 4510-4515 (1995).
    • (1995) J. Appl. Phys. , vol.78 , pp. 4510-4515
    • Yu, G.1    Heeger, A.J.2
  • 18
    • 2242470260 scopus 로고    scopus 로고
    • Enhanced emission and its switching in fluorescent organic nanoparticles
    • An, B.-K., Kwon, S.-K., Jung, S.-D. & Park, S. Y. Enhanced emission and its switching in fluorescent organic nanoparticles. J. Am. Chem. Soc. 124, 14410-14415 (2002).
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 14410-14415
    • An, B.-K.1    Kwon, S.-K.2    Jung, S.-D.3    Park, S.Y.4
  • 19
    • 33645855354 scopus 로고
    • The myth of the non-coordinating anion
    • Rosenthal, M. R. The myth of the non-coordinating anion. J. Chem. Educ. 50, 331-335 (1973).
    • (1973) J. Chem. Educ. , vol.50 , pp. 331-335
    • Rosenthal, M.R.1
  • 20
    • 4544301723 scopus 로고    scopus 로고
    • Highly efficient, one-step macrocyclizations assisted by the folding and preorganization of precursor oligomers
    • Yuan, L. et al. Highly efficient, one-step macrocyclizations assisted by the folding and preorganization of precursor oligomers. J. Am. Chem. Soc. 126, 11120-11121 (2004).
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 11120-11121
    • Yuan, L.1
  • 21
    • 58149197865 scopus 로고    scopus 로고
    • Crystallographic evidence of an unusual, pentagon-shaped folding pattern in a circular aromatic pentamer
    • Qin, B. et al. Crystallographic evidence of an unusual, pentagon-shaped folding pattern in a circular aromatic pentamer. Org. Lett. 10, 5127-5130 (2008).
    • (2008) Org. Lett. , vol.10 , pp. 5127-5130
    • Qin, B.1
  • 22
    • 78651299044 scopus 로고    scopus 로고
    • Campestarenes: Novel shapepersistent Schiff base macrocycles
    • Guieu, S., Crane, A. K. & MacLachlan, M. J. Campestarenes: Novel shapepersistent Schiff base macrocycles. Chem. Commun. 47, 1169-1171 (2011).
    • (2011) Chem. Commun. , vol.47 , pp. 1169-1171
    • Guieu, S.1    Crane, A.K.2    MacLachlan, M.J.3
  • 23
    • 0001664867 scopus 로고
    • Geometrically-controlled and site-specifically-functionalized phenylacetylene macrocycles
    • Zhang J., Pesak, D. J., Ludwick, J. L. & Moore, J. S. Geometrically-controlled and site-specifically-functionalized phenylacetylene macrocycles. J. Am. Chem. Soc. 116, 4227-4239 (1994).
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 4227-4239
    • Zhang, J.1    Pesak, D.J.2    Ludwick, J.L.3    Moore, J.S.4
  • 24
    • 81255210512 scopus 로고    scopus 로고
    • BOP-mediated one-pot synthesis of C5-symmetric macrocyclic pyridone pentamers
    • Du, Z. et al. BOP-mediated one-pot synthesis of C5-symmetric macrocyclic pyridone pentamers. Chem. Commun. 47, 12488-12490 (2011).
    • (2011) Chem. Commun. , vol.47 , pp. 12488-12490
    • Du, Z.1
  • 25
    • 77954646454 scopus 로고    scopus 로고
    • Persistently folded circular aromatic amide pentamers containing modularly tunable cation-binding cavities with high ion selectivity
    • Qin, B. et al. Persistently folded circular aromatic amide pentamers containing modularly tunable cation-binding cavities with high ion selectivity. J. Am. Chem. Soc. 132, 9564-9566 (2010).
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 9564-9566
    • Qin, B.1
  • 26
    • 80155143467 scopus 로고    scopus 로고
    • Crystallographic realization of the mathematically predicted densest all-pentagon packing lattice by c5-symmetric 'sticky' fluoropentamers
    • Ren, C. et al. Crystallographic realization of the mathematically predicted densest all-pentagon packing lattice by C5-symmetric 'sticky' fluoropentamers. Angew. Chem. Int. Ed. 50, 10612-10615 (2011).
    • (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 10612-10615
    • Ren, C.1
  • 27
    • 79961096584 scopus 로고    scopus 로고
    • Planar macrocyclic fluoropentamers as supramolecular organogelators
    • Ren, C., Xu, S., Xu, J., Chen, H. & Zeng, H. Planar macrocyclic fluoropentamers as supramolecular organogelators. Org. Lett. 13, 3840-3843 (2011).
    • (2011) Org. Lett. , vol.13 , pp. 3840-3843
    • Ren, C.1    Xu, S.2    Xu, J.3    Chen, H.4    Zeng, H.5
  • 28
    • 80052091620 scopus 로고    scopus 로고
    • Molecular pentagonal tiling: Self-assemblies of pentagonal-shaped macrocycles at liquid/solid interfaces
    • Tahara, K., Balandina, T., Furukawa, S., De Feyter, S. & Tobe, Y. Molecular pentagonal tiling: Self-assemblies of pentagonal-shaped macrocycles at liquid/solid interfaces. CrystEngComm 13, 5551-5558 (2011).
    • (2011) Cryst Eng Comm , vol.13 , pp. 5551-5558
    • Tahara, K.1    Balandina, T.2    Furukawa, S.3    De Feyter, S.4    Tobe, Y.5
  • 29
    • 0035815124 scopus 로고    scopus 로고
    • Polynucleating openchain systems with imidazole and proton-ionizable 1 ,2,4-triazole structural motifs
    • Alcalde, E., Ayala, C., Dinarès, I. & Mesquida, N. Polynucleating openchain systems with imidazole and proton-ionizable 1,2,4-triazole structural motifs. J. Org. Chem. 66, 2291-2295 (2001).
    • (2001) J. Org. Chem. , vol.66 , pp. 2291-2295
    • Alcalde, E.1    Ayala, C.2    Dinarès, I.3    Mesquida, N.4
  • 31
    • 0029856338 scopus 로고    scopus 로고
    • Five-fold symmetry in crystalline quasicrystal lattices
    • Caspar, D. L. D. & Fontano, E. Five-fold symmetry in crystalline quasicrystal lattices. Proc. Natl Acad. Sci. USA 93, 14271-14278 (1996).
    • (1996) Proc. Natl Acad. Sci. USA , vol.93 , pp. 14271-14278
    • Caspar, D.L.D.1    Fontano, E.2
  • 32
    • 78751565048 scopus 로고    scopus 로고
    • Stereoselective coordination of C5-symmetric corannulene derivatives with an enantiomerically pure [RhI(nbd)] metal complex
    • Bandera, D., Baldridge, K. K., Linden, A., Dorta, R. & Siegel, J. S. Stereoselective coordination of C5-symmetric corannulene derivatives with an enantiomerically pure [RhI(nbd)] metal complex. Angew. Chem. Int. Ed. 50, 865-867 (2011).
    • (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 865-867
    • Bandera, D.1    Baldridge, K.K.2    Linden, A.3    Dorta, R.4    Siegel, J.S.5
  • 33
    • 0000878272 scopus 로고
    • The crystal and molecular structure of corannulene c20h10
    • Hanson, J. C. & Nordman, C. E. The crystal and molecular structure of corannulene, C20H10. Acta Cryst. B 32, 1147-1153 (1976).
    • (1976) Acta Cryst. , vol.B32 , pp. 1147-1153
    • Hanson, J.C.1    Nordman, C.E.2
  • 34
    • 67749135582 scopus 로고    scopus 로고
    • Dipole-promoted and sizedependent cooperativity between pyridyl-containing triazolophanes and halides leads to persistent sandwich complexes with iodide
    • Li, Y., Pink, M., Karty, J. A. & Flood, A. H. Dipole-promoted and sizedependent cooperativity between pyridyl-containing triazolophanes and halides leads to persistent sandwich complexes with iodide. J. Am. Chem. Soc. 130, 17293-17295 (2008).
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 17293-17295
    • Li, Y.1    Pink, M.2    Karty, J.A.3    Flood, A.H.4
  • 35
    • 77958073620 scopus 로고    scopus 로고
    • Inherently chiral concave molecules - from synthesis to applications
    • Szumna, A. Inherently chiral concave molecules - from synthesis to applications. Chem. Soc. Rev. 39, 4274-4285 (2010).
    • (2010) Chem. Soc. Rev. , vol.39 , pp. 4274-4285
    • Szumna, A.1
  • 36
    • 84871966452 scopus 로고    scopus 로고
    • Asymmetric ion-pairing catalysis
    • Brak, K. & Jacobsen, E. N. Asymmetric ion-pairing catalysis. Angew. Chem. Int. Ed. 52, 534-561 (2013).
    • (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 534-561
    • Brak, K.1    Jacobsen, E.N.2
  • 37
    • 0036719443 scopus 로고    scopus 로고
    • Health effects assessment for environmental perchlorate contamination: The dose response for inhibition of thyroidal radioiodine uptake in humans
    • Greer, M. A., Goodman, G., Pleus, R. C. & Greer, S. E. Health effects assessment for environmental perchlorate contamination: The dose response for inhibition of thyroidal radioiodine uptake in humans. Environ. Health Persp. 110, 927-937 (2002).
    • (2002) Environ. Health Persp. , vol.110 , pp. 927-937
    • Greer, M.A.1    Goodman, G.2    Pleus, R.C.3    Greer, S.E.4
  • 39
    • 79955581216 scopus 로고    scopus 로고
    • Selective anion binding by a 'chameleon' capsule with a dynamically reconfigurable exterior
    • Hristova, Y. R., Smulders, M. M. J., Clegg, J. K., Breiner, B. & Nitschke, J. R. Selective anion binding by a 'chameleon' capsule with a dynamically reconfigurable exterior. Chem. Sci. 2, 638-641 (2011).
    • (2011) Chem. Sci. , vol.2 , pp. 638-641
    • Hristova, Y.R.1    Smulders, M.M.J.2    Clegg, J.K.3    Breiner, B.4    Nitschke, J.R.5
  • 40
    • 0037119653 scopus 로고    scopus 로고
    • Jr Molecular encapsulation of anions in a neutral receptor
    • Hayashida, O., Shivanyuk, A. & Rebek, J. Jr Molecular encapsulation of anions in a neutral receptor. Angew. Chem. Int. Ed. 41, 3423-3426 (2002).
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 3423-3426
    • Hayashida, O.1    Shivanyuk, A.2    Rebek, J.3
  • 42
    • 79955878936 scopus 로고    scopus 로고
    • Anion binding to hydrophobic concavity is central to the salting-in effects of Hofmeister chaotropes
    • Gibb, C. L. D. & Gibb, B. C. Anion binding to hydrophobic concavity is central to the salting-in effects of Hofmeister chaotropes. J. Am. Chem. Soc. 133, 7344-7347 (2011).
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 7344-7347
    • Gibb, C.L.D.1    Gibb, B.C.2
  • 44
    • 4544353066 scopus 로고    scopus 로고
    • Shuttling through anion recognition
    • Keaveney, C. M. & Leigh, D. A. Shuttling through anion recognition. Angew. Chem. Int. Ed. 43, 1222-1224 (2004).
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 1222-1224
    • Keaveney, C.M.1    Leigh, D.A.2
  • 45
    • 0035896348 scopus 로고    scopus 로고
    • Photoinduction of fast, reversible translational motion in a hydrogen-bonded molecular shuttle
    • Brouwer, A. M. et al. Photoinduction of fast, reversible translational motion in a hydrogen-bonded molecular shuttle. Science 291, 2124-2128 (2001).
    • (2001) Science , vol.291 , pp. 2124-2128
    • Brouwer, A.M.1
  • 46
    • 0036432918 scopus 로고    scopus 로고
    • Novel template effect for the preparation of [2]rotaxanes with functionalized centre pieces
    • Ghosh, P., Mermagen, O. & Schalley, C. A. Novel template effect for the preparation of [2]rotaxanes with functionalized centre pieces. Chem. Commun. 2628-2629 (2002).
    • (2002) Chem. Commun. , pp. 2628-2629
    • Ghosh, P.1    Mermagen, O.2    Schalley, C.A.3
  • 47
    • 62749094403 scopus 로고    scopus 로고
    • Hybrid organic-inorganic rotaxanes and molecular shuttles
    • Lee, C. F. et al. Hybrid organic-inorganic rotaxanes and molecular shuttles. Nature 458, 314-318 (2009).
    • (2009) Nature , vol.458 , pp. 314-318
    • Lee, C.F.1
  • 49
    • 0001603015 scopus 로고    scopus 로고
    • Self-assembling [2]- and [3]rotaxanes from secondary dialkylammonium salts and crown ethers
    • Ashton, P. R. et al. Self-assembling [2]- and [3]rotaxanes from secondary dialkylammonium salts and crown ethers. Chem. Eur. J. 2, 729-736 (1996).
    • (1996) Chem. Eur. J. , vol.2 , pp. 729-736
    • Ashton, P.R.1
  • 52
    • 79955430443 scopus 로고    scopus 로고
    • Sequence stereoisomerism in calixarene-based pseudo [3]rotaxanes
    • Talotta, C., Gaeta, C., Pierro, T. & Neri, P. Sequence stereoisomerism in calixarene-based pseudo[3]rotaxanes. Org. Lett. 13, 2098-2101 (2011).
    • (2011) Org. Lett. , vol.13 , pp. 2098-2101
    • Talotta, C.1    Gaeta, C.2    Pierro, T.3    Neri, P.4
  • 53
    • 38949158373 scopus 로고    scopus 로고
    • Detailed spectroscopic, thermodynamic, and kinetic characterization of nickel(II) complexes with 2,2′-bipyridine and 1,10-phenanthroline attained via equilibrium-restricted factor analysis
    • Vander Griend, D. A., Bediako, D. K., DeVries, M. J., DeJong, N. A. & Heeringa, L. P. Detailed spectroscopic, thermodynamic, and kinetic characterization of nickel(II) complexes with 2,2′-bipyridine and 1,10-phenanthroline attained via equilibrium-restricted factor analysis. Inorg. Chem. 47, 656-662 (2008).
    • (2008) Inorg. Chem. , vol.47 , pp. 656-662
    • Vander Griend, D.A.1    Bediako, D.K.2    DeVries, M.J.3    DeJong, N.A.4    Heeringa, L.P.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.