Symmetrical electron-deficient materials incorporating azaheterocycles

K. Pieterse, A. Lauritsen, A.P.H.J. Schenning, J.A.J.M. Vekemans, E.W. Meijer

Research output: Contribution to journalArticleAcademicpeer-review

67 Citations (Scopus)
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Abstract

To investigate the potential of di- and tri-azaheterocycles as building blocks for pi-conjugated materials with high electron affinity, linear oligomers incorporating pyrazine and a C(3)-symmetric discotic molecule based on triazine were synthesized. The tridodecyloxyphenyl end-capped ethynylene pyrazinylene oligomers showed remarkable solvatochroism in absorption and emission in solution. The oligomers containing one and two pyrazine rings displayed liquid crystallinity in the solid state. The largest ethynylene pyrazinylene oligomer containing three pyrazine rings had the lowest first reduction potential at -1.08 V. The triazine-derived discotic molecule exhibited UV/Vis and fluorescence behavior comparable to that of the linear oligomers and featured a first reduction potential at -1.49 V, somewhat lower than expected. [on SciFinder (R)]
Original languageEnglish
Pages (from-to)5597-5604
Number of pages8
JournalChemistry : A European Journal
Volume9
Issue number22
DOIs
Publication statusPublished - 2003

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