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Volumn 44, Issue 10, 2011, Pages 3685-3687

Arylene-ethynylene macrocycles via depolymerization-macrocyclization

Author keywords

[No Author keywords available]

Indexed keywords

AEROBIC CONDITION; ALKYNE METATHESIS; ARYLENE; CRUDE REACTION MIXTURES; LOW MOLECULAR WEIGHT; MACROCYCLES; MOLECULAR WEIGHT POLYMERS; MONODISPERSE; MONOMETHYL ETHERS; OXIDATIVE COUPLINGS; SIDE-CHAINS; SONOGASHIRA COUPLING; TERMINAL ALKYNE; THERMODYNAMIC CONDITIONS; TRIETHYLENE GLYCOL;

EID: 79960013010     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma2006552     Document Type: Article
Times cited : (36)

References (30)
  • 13
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    • Following Furstner's molybdenum nitride work, we have found that Ph3SiOH is an alternative ligand for our molybdenum alkylidynes. See: Following Furstner's molybdenum nitride work, we have found that Ph3SiOH is an alternative ligand for our molybdenum alkylidynes. See: (c) Bindl, M.; Stade, R.; Heilmann, E. K.; Picot, A.; Goddard, R.; Fürstner, A. J. Am. Chem. Soc. 2009, 131, 9468-9470.
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 9468-9470
    • Bindl, M.1    Stade, R.2    Heilmann, E.K.3    Picot, A.4    Goddard, R.5    Fürstner, A.6
  • 16
    • 23944458125 scopus 로고    scopus 로고
    • Initial evidence in support of this method was provided on small scale using a m-phenyleneéthynylene polymer; however, the formation exclusively of the corresponding hexacycle failed. See: Zhang, W.; Moore, J. S. J. Am. Chem. Soc. 2005, 127, 11863-11870.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 11863-11870
    • Zhang, W.1    Moore, J.S.2
  • 17
    • 0017243116 scopus 로고
    • A related concept is cyclodepolymerization (CDP), which is the conversion of polymers to their corresponding cyclic oligomers. See: (a) Semlyen, J. A. Adv. Polym. Sci. 1976, 21, 41-75.
    • (1976) Adv. Polym. Sci. , vol.21 , pp. 41-75
    • Semlyen, J.A.1
  • 18
    • 0002454235 scopus 로고
    • Allen, G., Bevington, J. C., Eds.; Pergamon: Oxford, UK
    • (b) Suter, U. W. In Comprehensive Polymer Science; Allen, G., Bevington, J. C., Eds.; Pergamon: Oxford, UK, 1989; Vol. 5, p 91.
    • (1989) Comprehensive Polymer Science , vol.5 , pp. 91
    • Suter, U.W.1
  • 25
    • 0037130013 scopus 로고    scopus 로고
    • 3,6-Carbazolylethynylene polymers have also been synthesized by Bunz and co-workers using alkyne metathesis in an attempt to obtain the cyclic tetramer; however, the latter was formed in too low of yield to be isolated (see: Brizius, G.; Kroth, S.; Bunz, U. H. F. Macromolecules 2002, 35, 5317-5319).
    • (2002) Macromolecules , vol.35 , pp. 5317-5319
    • Brizius, G.1    Kroth, S.2    Bunz, U.H.F.3
  • 26
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  • 28
    • 77953099583 scopus 로고    scopus 로고
    • Hopkins also saw lack of productive diyne metathesis with similar tungsten species (see: Shaner, S. E.; Sun, J.; Hopkins, M. D. Polym. Prepr. 2009, 50, 346-347).
    • (2009) Polym. Prepr , vol.50 , pp. 346-347
    • Shaner, S.E.1    Sun, J.2    Hopkins, M.D.3
  • 29
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    • Hay, A. J. Org. Chem. 1960, 25, 1275-1276.
    • (1960) J. Org. Chem. , vol.25 , pp. 1275-1276
    • Hay, A.1
  • 30
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    • The low molecular weight material was successfully removed by swelling and washing with dichloromethane. MALDI-MS analysis shows the mixture contains macrocyclic species (m/z = 1229 [3]cycle, 1638 [4]cycle). Similar macrocycles have been reported by: Zhao, T.; Liu, Z.; Song, Y.; Xu, W.; Zhang, D.; Zhu, D. J. Org. Chem. 2006, 71, 7422-7432.
    • (2006) J. Org. Chem. , vol.71 , pp. 7422-7432
    • Zhao, T.1    Liu, Z.2    Song, Y.3    Xu, W.4    Zhang, D.5    Zhu, D.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.