메뉴 건너뛰기




Volumn 62, Issue 7, 2006, Pages 1485-1493

The synthesis of bis(oligophenyleneethynylenes): Novel potential nonlinear optical materials

Author keywords

Alkynes; Nonlinear optics; Sonogashira coupling

Indexed keywords

1,8 BIS[3 (METHOXYCARBONYL) 4 (PHENYLETHYNYL) PHENYLETHYNYL] 10 METHOXYANTHRACENE; 1,8 BIS[3 [METHOXYCARBONYL] 4 [3 (METHOXYCARBONYL) 4 (PHENYLETHYNYL) PHENYLETHYNYL]PHENYLETHYNYL] 10 METHOXYANTHRACENE; ALKENE DERIVATIVE; BIS(OLIGOPHENYLENEETHYNYLENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 30744455995     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.11.015     Document Type: Article
Times cited : (12)

References (73)
  • 1
    • 0002235077 scopus 로고
    • Materials for Nonlinear Optics: Chemical Perspectives
    • American Chemical Society Washington, DC
    • For a general overview of NLO physics, basic design principles and application of NLO materials, see: S.R. Marder J.E. Sohn G.D. Stucky Materials for Nonlinear Optics: Chemical Perspectives ACS Symposium Series 455 1991 American Chemical Society Washington, DC
    • (1991) ACS Symposium Series 455
    • Marder Sohn, J.E.S.R.1    Stucky, G.D.2
  • 31
    • 0030789178 scopus 로고    scopus 로고
    • For attempts to restrict the rotation of aryl fragments by covalent linking, see: (a) G.T. Crisp, and T.P. Bubner Tetrahedron 53 1997 11881 11898
    • (1997) Tetrahedron , vol.53 , pp. 11881-11898
    • Crisp, G.T.1    Bubner, T.P.2
  • 41
    • 84877274207 scopus 로고
    • For recent reviews on the Pd-catalyzed cross coupling of alkynes with arenes, heteroarenes and alkenes, including the Sonogashira reaction, see: (a) R. Rossi, A. Carpita, and F. Bellina Org. Prep. Proced. Int. 27 1995 127 160
    • (1995) Org. Prep. Proced. Int. , vol.27 , pp. 127-160
    • Rossi, R.1    Carpita, A.2    Bellina, F.3
  • 44
    • 30744432217 scopus 로고    scopus 로고
    • Balavoine, F.; Schultz, P.; Mioskowski, C.; Patent WO 9961912, 1999.
    • (b) Balavoine, F.; Schultz, P.; Mioskowski, C.; Patent WO 9961912, 1999.
  • 50
    • 1842740801 scopus 로고    scopus 로고
    • For reviews of Pd-catalyzed amination, see: (a) J.F. Hartwig Synlett 1997 329 340
    • (1997) Synlett , pp. 329-340
    • Hartwig, J.F.1
  • 54
    • 30744449607 scopus 로고    scopus 로고
    • note
    • Chromatography of 1,8-bis(phenylethynyl)anthracenes bearing free hydroxyl or amino groups was found to be extremely difficult in previous work; see Ref. 14
  • 55
    • 0029933331 scopus 로고    scopus 로고
    • Pd-catalyzed cross-coupling was the preferred method for the construction of OPEs because of the mild reaction conditions. For complimentary approaches to OPE synthesis, see: (a) O. Lavastre, L. Ollivier, P.H. Dixneuf, and S. Sibandhit Tetrahedron 52 1996 5495 5504
    • (1996) Tetrahedron , vol.52 , pp. 5495-5504
    • Lavastre, O.1    Ollivier, L.2    Dixneuf, P.H.3    Sibandhit, S.4
  • 59
    • 30744448017 scopus 로고    scopus 로고
    • note
    • 1H NMR of the crude products, which also showed no purification of the terminal alkynes was necessary, and these were immediately used in further coupling reactions to minimize oxidative dimerization.
  • 60
    • 3242752645 scopus 로고    scopus 로고
    • After this work was carried out, an article was published showing that the rate of TBAF-induced hydrolysis of aryl triflates bearing electron-withdrawing groups in the para-position was greatly enhanced; see: T. Ohgiya, and S. Nishiyama Tetrahedron Lett. 45 2004 6317 6320
    • (2004) Tetrahedron Lett. , vol.45 , pp. 6317-6320
    • Ohgiya, T.1    Nishiyama, S.2
  • 61
    • 85077747585 scopus 로고
    • For a review of stilbene syntheses, see: K.B. Becker Synthesis 1983 341 368
    • (1983) Synthesis , pp. 341-368
    • Becker, K.B.1
  • 62
    • 20544450502 scopus 로고    scopus 로고
    • A. de Meijre F. Diedrich 2nd ed. Wiley-VCH Weinheim
    • For a review of the Heck reaction, see: S. Braese, and A. de Meijre A. de Meijre F. Diedrich Metal-Catalysed Cross-Coupling Reactions 2nd ed. 2004 Wiley-VCH Weinheim 217 315
    • (2004) Metal-Catalysed Cross-Coupling Reactions , pp. 217-315
    • Braese, S.1    De Meijre, A.2
  • 65
    • 2042507954 scopus 로고
    • For reviews of the Suzuki reaction, see: (a) N. Miyaura, and A. Suzuki Chem. Rev. 95 1995 2457 2483
    • (1995) Chem. Rev. , vol.95 , pp. 2457-2483
    • Miyaura, N.1    Suzuki, A.2
  • 73


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.