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Volumn 45, Issue 27, 2006, Pages 4416-4439

Shape-persistent macrocycles: Structures and synthetic approaches from arylene and ethynylene building blocks

Author keywords

Cross coupling; Cyclooligomerization; Dynamic covalent chemistry; Metathesis; Shape persistent macrocycles

Indexed keywords

COMPLEXATION; OLIGOMERS; REACTION KINETICS; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS (CHEMICAL); THERMODYNAMIC PROPERTIES;

EID: 33746375650     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200503988     Document Type: Review
Times cited : (515)

References (190)
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    • (Eds.: P. J. Stang, F. Diederich), VCH, Weinheim, chap. 12
    • J. K. Young, J. S. Moore in Modern Acetylene Chemistry (Eds.: P. J. Stang, F. Diederich), VCH, Weinheim, 1995, chap. 12.
    • (1995) Modern Acetylene Chemistry
    • Young, J.K.1    Moore, J.S.2
  • 14
    • 27944490359 scopus 로고    scopus 로고
    • Recently Yaghi and co-workers reported their synthesis of covalent organic frameworks (COFs) by condensation reactions of phenyldiboronic acid and hexahydroxytriphenylene. The highly crystalline products apparently formed expanded porous graphitic layers that are either staggered or eclipsed, as determined by powder x-ray diffraction studies (A. P. Côté, A. I. Benin, N. W. Ockwig, M. O'Keeffe, A. J. Matzger, O. M. Yaghi, Science 2005, 310, 1166).
    • (2005) Science , vol.310 , pp. 1166
    • Côté, A.P.1    Benin, A.I.2    Ockwig, N.W.3    O'Keeffe, M.4    Matzger, A.J.5    Yaghi, O.M.6
  • 48
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    • (Ed.: R. H. Grubbs), Wiley-VCH, Weinheim, chap. 2.12
    • d) A. Fürstner in Handbook of Metathesis, Vol. 2 (Ed.: R. H. Grubbs), Wiley-VCH, Weinheim, 2003, chap. 2.12;
    • (2003) Handbook of Metathesis, Vol. 2 , vol.2
    • Fürstner, A.1
  • 50
    • 13744255681 scopus 로고    scopus 로고
    • The formation of porphyrins and calixarenes by pyrrole- or phenol-aldehyde condensations, repectively, are cyclooligomerization examples, see a) A. Ghosh, Angew. Chem. 2004, 116, 1952;
    • (2004) Angew. Chem. , vol.116 , pp. 1952
    • Ghosh, A.1
  • 59
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    • a) B. M. Trost, Science 1991, 254, 1471;
    • (1991) Science , vol.254 , pp. 1471
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  • 86
    • 33746363629 scopus 로고    scopus 로고
    • All the simple kinetic simulations were performed by using a mechanism-based kinetics simulator located at http://www.stolaf.edu/depts/ chemistry/courses/toolkits/126/js/kinetics/ index.htm.
  • 102
    • 0003559584 scopus 로고
    • Wiley, Chichester
    • For examples of hypsochromic effects observed in aromatic macrocycles and polymers with π-π interactions, see a) F. Vögtle, Cyclophane Chemistry, Wiley, Chichester, 1993, p. 77;
    • (1993) Cyclophane Chemistry , pp. 77
    • Vögtle, F.1
  • 119
    • 16444362108 scopus 로고    scopus 로고
    • Recently, a donor-acceptor-substituted phenyleneethynylene macrocycle was prepared through a similar approach: B. Traber, T. Oeser, R. Gleiter, Eur. J. Org. Chem. 2005, 1283.
    • (2005) Eur. J. Org. Chem. , pp. 1283
    • Traber, B.1    Oeser, T.2    Gleiter, R.3
  • 146
    • 33746341283 scopus 로고    scopus 로고
    • Wavefunction, Inc.; Irvine, California
    • Spartan software (version 4.0; Wavefunction, Inc.; Irvine, California) at the AM1 level was used to estimate the heats of formation for the methoxy-substituted macrocycles.
    • Spartan Software (version 4.0)
  • 147
    • 3343012187 scopus 로고    scopus 로고
    • For reviews, see a) R. H. Grubbs, Tetrahedron 2004, 60, 7117;
    • (2004) Tetrahedron , vol.60 , pp. 7117
    • Grubbs, R.H.1
  • 153
    • 0344006321 scopus 로고    scopus 로고
    • and Ref. [34b]
    • Angew. Chem. Int. Ed. 2000, 39, 3012, and Ref. [34b].
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3012
  • 162
    • 33746357685 scopus 로고    scopus 로고
    • note
    • Analogous to the synthesis of macrocycle 85, the yields reported herein are unlikely to truly reflect the distribution of the thermodynamically controlled products.
  • 166
    • 33746367559 scopus 로고    scopus 로고
    • note
    • The reported yields may not truly reflect the thermodynamically controlled product distribution.
  • 168
    • 2942527303 scopus 로고    scopus 로고
    • The same approach was also successfully applied to the synthesis of conjugated arylene ethynylene polymers with high molecular weight at room temperature, see W. Zhang, J. S. Moore, Macromolecules 2004, 37, 3973.
    • (2004) Macromolecules , vol.37 , pp. 3973
    • Zhang, W.1    Moore, J.S.2
  • 171
    • 33746351864 scopus 로고    scopus 로고
    • note
    • A small amount of pentameric macrocycles are obtained as the major side product in these cases.
  • 176
    • 0034815849 scopus 로고    scopus 로고
    • The tetrameric carbazole macrocycle 96 was first synthesized in 14.3 % yield by a cross-coupling approach: S. Maruyama, H. Hokari, T. Wada, H. Sasabe, Synthesis 2001, 1794.
    • (2001) Synthesis , pp. 1794
    • Maruyama, S.1    Hokari, H.2    Wada, T.3    Sasabe, H.4
  • 177
    • 33846697120 scopus 로고    scopus 로고
    • submitted
    • Recently, another 1,1-dimethyltridecylcarboxylate-functionalized carbazole-based macrocycle has also been prepared through the precipitation-driven alkyne metathesis, W. Zhang, H. M. Cho, J. S. Moore, Org. Synth., submitted.
    • Org. Synth.
    • Zhang, W.1    Cho, H.M.2    Moore, J.S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.