Synthesis and Characterization of Liquid-Crystalline Tetraoxapentacene Derivatives Exhibiting Aggregation-Induced Emission
Lana K. Hiscock
Department of Chemistry and Biochemistry, Wilfrid Laurier University, 75 University Ave. W., Waterloo, ON, N2L 3C5 Canada
Search for more papers by this authorBrooke M. Raycraft
Department of Chemistry and Biochemistry, Wilfrid Laurier University, 75 University Ave. W., Waterloo, ON, N2L 3C5 Canada
Search for more papers by this authorMonika Wałęsa-Chorab
Département de Chimie, Université de Montréal, CP 6128, Centre-ville Montreal, QC, H3C 3J7 Canada
Current address: Faculty of Chemistry, Adam Mickiewicz University in Poznań, Umultowska 89b, 61614 Poznań, Poland
These authors contributed equally to this work.
Search for more papers by this authorCoralie Cambe
Département de Chimie, Université de Montréal, CP 6128, Centre-ville Montreal, QC, H3C 3J7 Canada
These authors contributed equally to this work.
Search for more papers by this authorAlexandre Malinge
Département de Chimie, Université de Montréal, CP 6128, Centre-ville Montreal, QC, H3C 3J7 Canada
These authors contributed equally to this work.
Search for more papers by this authorProf. Dr. W. G. Skene
Département de Chimie, Université de Montréal, CP 6128, Centre-ville Montreal, QC, H3C 3J7 Canada
Search for more papers by this authorHi Taing
Department of Chemistry and Biochemistry, University of Windsor, Essex Hall, 401 Sunset Ave., Windsor, ON, N9B 3P4 Canada
Search for more papers by this authorProf. Dr. S. Holger Eichhorn
Department of Chemistry and Biochemistry, University of Windsor, Essex Hall, 401 Sunset Ave., Windsor, ON, N9B 3P4 Canada
Search for more papers by this authorProf. Dr. Louise N. Dawe
Department of Chemistry and Biochemistry, Wilfrid Laurier University, 75 University Ave. W., Waterloo, ON, N2L 3C5 Canada
Search for more papers by this authorCorresponding Author
Prof. Dr. Kenneth E. Maly
Department of Chemistry and Biochemistry, Wilfrid Laurier University, 75 University Ave. W., Waterloo, ON, N2L 3C5 Canada
Search for more papers by this authorLana K. Hiscock
Department of Chemistry and Biochemistry, Wilfrid Laurier University, 75 University Ave. W., Waterloo, ON, N2L 3C5 Canada
Search for more papers by this authorBrooke M. Raycraft
Department of Chemistry and Biochemistry, Wilfrid Laurier University, 75 University Ave. W., Waterloo, ON, N2L 3C5 Canada
Search for more papers by this authorMonika Wałęsa-Chorab
Département de Chimie, Université de Montréal, CP 6128, Centre-ville Montreal, QC, H3C 3J7 Canada
Current address: Faculty of Chemistry, Adam Mickiewicz University in Poznań, Umultowska 89b, 61614 Poznań, Poland
These authors contributed equally to this work.
Search for more papers by this authorCoralie Cambe
Département de Chimie, Université de Montréal, CP 6128, Centre-ville Montreal, QC, H3C 3J7 Canada
These authors contributed equally to this work.
Search for more papers by this authorAlexandre Malinge
Département de Chimie, Université de Montréal, CP 6128, Centre-ville Montreal, QC, H3C 3J7 Canada
These authors contributed equally to this work.
Search for more papers by this authorProf. Dr. W. G. Skene
Département de Chimie, Université de Montréal, CP 6128, Centre-ville Montreal, QC, H3C 3J7 Canada
Search for more papers by this authorHi Taing
Department of Chemistry and Biochemistry, University of Windsor, Essex Hall, 401 Sunset Ave., Windsor, ON, N9B 3P4 Canada
Search for more papers by this authorProf. Dr. S. Holger Eichhorn
Department of Chemistry and Biochemistry, University of Windsor, Essex Hall, 401 Sunset Ave., Windsor, ON, N9B 3P4 Canada
Search for more papers by this authorProf. Dr. Louise N. Dawe
Department of Chemistry and Biochemistry, Wilfrid Laurier University, 75 University Ave. W., Waterloo, ON, N2L 3C5 Canada
Search for more papers by this authorCorresponding Author
Prof. Dr. Kenneth E. Maly
Department of Chemistry and Biochemistry, Wilfrid Laurier University, 75 University Ave. W., Waterloo, ON, N2L 3C5 Canada
Search for more papers by this authorGraphical Abstract
A series of aryl substituted dicyanotetraoxapentacenes were prepared by reaction of the appropriate catechol derivatives with tetrafluoroterephthalonitrile. These compounds exhibit columnar liquid-crystalline phases, aggregation-induced emission in solution, and efficient luminescence in the solid state.
Abstract
A series of new tetrakis(dialkoxyphenyl) dicyanotetraoxapentacene derivatives (1 a–c) were prepared by reaction of the appropriate terphenyl diols with tetrafluoroterephthalonitrile in good yields. Compounds 1 b and 1 c, which bear hexyloxy and decyloxy side chains, exhibited columnar hexagonal mesophases, as shown by polarized optical microscopy, variable-temperature powder X-ray diffraction, and differential scanning calorimetry. Single-crystal X-ray diffraction of methoxy-substituted 1 a revealed that the dicyanotetraoxapentacene core is highly planar, consistent with the notion that these molecules are able to stack in columnar mesophases. A detailed photophysical characterization showed that these compounds exhibit aggregation-induced emission in solution, emission in nonpolar solvents, weak emission in polar solvents, and strong emission in the solid state both as powder and in thin films. These observations are consistent with a weakly emissive charge-transfer state in polar solvents and a more highly emissive locally excited state in nonpolar solvents.
Conflict of interest
The authors declare no conflict of interest.
Supporting Information
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