Synthesis of Monofunctionalized p-Quaterphenyls

Abstract

p-Oligophenyls have proven to be versatile building blocks for the generation of self-assembled nanoaggregates via vapor deposition on solid supports whose optical properties and morphologies can be influenced by the introduction of functional groups. Nonsymmetrically functionalized p,p′-disubstituted derivatives could even be demonstrated to form nanoaggregates that can act as frequency doublers due to their nonlinear optical properties.

Similar properties can be expected from monofunctionalized derivatives. Thus, we developed a general approach for the synthesis of monofunctionalized 1,1′:4′,1′′:4′′,1′′′-quaterphenyls (p-quaterphenylenes) through the application of a reliable Suzuki cross-coupling strategy.

Key words

cross-coupling reaction - p-oligophenyls - rodlike molecules - Suzuki cross-coupling

References

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12

Koch, R.; Finnerty, J. J.; Bruhn, T. J. Phys. Org. Chem. submitted for publication.

15

In the past p-quaterphenyl syntheses were achieved by cyclotrimerizations of acetylenes, Diels-Alder reactions of cyclopentadienones and subsequent aromatization, Wittig reactions of cinnamaldehydes followed by Diels-Alder reactions with acetylenedicarboxylates and subsequent aromatization, addition of Grignard reagents to arenes, Grignard reactions with p-quinones and subsequent dehydration, or Ullmann-type coupling reactions. For a detailed list of references see citations 20-25 listed in ref 9.

16

For a detailed list of references see citations 26-30 listed in ref 9.

22

This compound has been described in some Japanese patents, however, without any data concerning its synthesis no characterization.