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Synthesis 2002(9): 1185-1190
DOI: 10.1055/s-2002-32537
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Properties of Photoluminescent 1,4-Bis-(α-cyano-4-methoxystyryl)benzenes

Christiane Löwea,b, Christoph Weder*b
a On leave from the Swiss Federal Laboratories for Materials Testing and Research (EMPA), Ueberlandstrasse 129, 8600 Dübendorf, Switzerland
b Department of Macromolecular Science and Engineering, Case Western Reserve University, 2100 Adelbert Road, Cleveland Ohio 44106-7202, USA
Fax: +1(216)3684202; e-Mail: chw6@po.cwru.edu;
Further Information

Publication History

Received 11 April 2002
Publication Date:
28 June 2002 (online)

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Abstract

1,4-Bis-(α-cyano-4-methoxystyryl)benzene (1a) and 1,4-bis-(α-cyano-4-methoxystyryl)-2,5-dimethoxybenzene (1b) were synthesized by the Knoevenagel reaction of (4-methoxyphenyl)acetonitrile with terephthaldicarboxyaldehyde and 2,5-dimethoxy terephthaldicarboxyaldehyde, respectively. Both phenylene vinylene oligomers are highly photoluminescent, and the comparison of the emission spectra of the crystalline solids with the ones of the corresponding low-viscosity molecular solutions reveals, particularly in case of 1b, an extremely large bathochromic shift. This effect is consistent with the formation of excimers that are characterized by low-bandgap emission. With the objective to control the emission characteristics of these dyes beyond the limiting states of molecular solution and crystalline solid, the investigation of their photophysical characteristics was extended to the liquid crystalline state and the isotropic melt, as well as to blends with isotactic polypropylene.

Key words

phenylene vinylene oligomer - photoluminescence - liquid crystal - excimer luminescence - Knoevenagel reaction - colour tuning

    References

  • 1a Kraft A. Grimsdale AC. Holmes AB. Angew. Chem. Int. Ed.  1998,  37:  403 
    CrossrefGoogle Scholar
  • 1b Mitschke U. Bäuerle P. J. Mater. Chem.  2000,  10:  1471 
    CrossrefGoogle Scholar
  • 1c Greiner A. Weder C. Application of Polymeric Materials in LEDs, In Encyclopedia of Polymer Science and Technology   Kroschwitz JI. Wiley-Interscience; New York: 2001. 
    CrossrefGoogle Scholar
  • 2a Gill RE. van Hutten PF. Meetsma A. Hadziioannou G. Chem. Mater.  1996,  8:  1341 
    CrossrefGoogle Scholar
  • 2b van Hutten PF. Krasnikov VV. Brouwer H.-J. Hadziiouannou G. Chem. Phys.  1999,  241:  139 
    CrossrefGoogle Scholar
  • 3a Döttinger SE. Hohloch M. Hohnholz D. Segura JL. Steinhuber E. Hanack M. Synth. Met.  1997,  84:  267 
    CrossrefGoogle Scholar
  • 3b Hohloch M. Maichle-Mössmer C. Hanack M. Chem. Mater.  1998,  10:  1327 
    CrossrefGoogle Scholar
  • 3c Oelkrug D. Tompert A. Gierschner J. Egelhaaf H.-J. Hanack M. Hohloch M. Steinhuber E. J. Phys. Chem. B  1998,  102:  1902 
    CrossrefGoogle Scholar
  • 3d Martinez-Ruiz P. Behnisch B. Schweikart K.-H. Hanack M. Lüer L. Oelkrug D. Chem.-Eur. J.  2000,  6:  1294 
    CrossrefGoogle Scholar
  • 3e Freudenmann R. Behnisch B. Hanack M. J. Mater Chem.  2001,  11:  1618 
    CrossrefGoogle Scholar
  • 4 Henari FZ. Manaa H. Kretsch KP. Blau WJ. Rost H. Pfeiffer S. Teuschel A. Tillmann H. Hörhold HH. Chem. Phys. Lett.  1999,  307:  163 
    CrossrefGoogle Scholar
  • 5 de Souza MM. Rumbles G. Gould IR. Amer H. Samuel IDW. Moratti SC. Holmes AB. Synth. Met.  2000,  111-112:  539 
    Google Scholar
  • 6a Greenham NC. Moratti SC. Bradley DDC. Friend RH. Holmes AB. Nature  1993,  365:  628 
    Google Scholar
  • 6b Moratti SC. Cervini R. Holmes AB. Baigent DR. Friend RH. Synth. Met.  1995,  71:  2117 
    Google Scholar
  • 6c Hanack M. Segura JL. Spreitzer H. Adv. Mater.  1996,  8:  663 
    Google Scholar
  • 6d Hohloch M. Segura JL. Döttinger SE. Hohnholz D. Steinhuber E. Spreitzer H. Hanack M. Synth. Met.  1997,  84:  319 
    Google Scholar
  • 7 Gilbert A. Baggott J. Essentials of Molecular Photochemistry   Blackwell Science; Oxford: 1991. 
    Google Scholar
  • See for example:
  • 8a Montali A. Bastiaansen C. Smith P. Weder C. Nature  1998,  392:  261 
    CrossrefGoogle Scholar
  • 8b Weder C. Sarwa C. Montali A. Bastiaansen C. Smith P. Science  1998,  279:  835 
    CrossrefGoogle Scholar
  • 8c Broer DJ. van Haaren JAMM. van de Witte P. Bastiaansen C. Macromol. Symp.  2000,  154:  1 
    CrossrefGoogle Scholar
  • 8d Springle I. Bayley P. Crossland W. Needham B. Davey A. Macromol. Symp.  2000,  154:  37 
    CrossrefGoogle Scholar
  • 8e Kocher C. Montali A. Smith P. Weder C. Adv. Funct. Mater.  2001,  11:  31 
    CrossrefGoogle Scholar
  • 9a Tayama T. inventors; Jpn. Kokai Tokkyo Koho JP  63096170.  ; Chem. Abstr. 1988, 109, 231702
  • 9b Miyabayashi M, Iimura K, and Ujiie S. inventors; Eur. Pat. Appl. EP  427962.  ; Chem. Abstr. 1991, 115, 137031
  • 9c Iimura K, Ujiie S, and Myabayashi M. inventors; Jpn. Kokai Tokkyo Koho JP  03127767.  ; Chem. Abstr. 1991, 115, 291920
  • 9d Ota M, Onuma T, Kawamura F, Sakon H, and Takahashi T. inventors; Jpn. Kokai Tokkyo Koho JP  03205478.  ; Chem. Abstr. 1992, 116, 139767
  • 10 Gray GW. Goodby JWG. Smectic Liquid Crystals: Textures and Structures   Leonard Hill; Glasgow: 1984. 
    Google Scholar
  • 11 Birks JB. Photophysics of Aromatic Molecules   Wiley-Interscience; Chichester: 1970. 
    Google Scholar
  • 12 Eglin M. Montali A. Palmans ARA. Tervoort T. Smith P. Weder C. J. Mater. Chem.  1999,  9:  2221 
    CrossrefGoogle Scholar