The synthesis of boron subphthalocyanines (BsubPc) from modified phthalonitriles is reported. The BsubPcs have intense red-shifted absorption compared to normal BsubPcs and readily tuneable optoelectronic properties including enhanced electrochemical stability and the presence of up to two reversible electrochemical reductions.
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The influence of the axial group on the crystal structures of boron subphthalocyanines.
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Department of Chemical Engineering and Applied Chemistry, University of Toronto, 200 College Street, Toronto, Ontario, M5S 3E5, Canada.
The crystal structures of 16 boron subphthalocyanines (BsubPcs) with structurally diverse axial groups were analyzed and compared to elucidate the impact of the axial group on the intermolecular π-π interactions, axial-group interactions, axial bond length and BsubPc bowl depth. π-π interactions between the isoindole units of adjacent BsubPc molecules most often involve concave-concave packing, whereas axial-group interactions with adjacent BsubPc molecules tend to favour the convex side of the BsubPc bowl. Furthermore, axial groups that contain O and/or F atoms tend to have significant hydrogen-bonding interactions, while axial groups containing arene site(s) can participate in π-π interactions with the BsubPc bowl, both of which can strongly influence the crystal packing.
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Organic Electronics Research Center, Ming Chi University of Technology, New Taipei City 24301, Taiwan.
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Department of Applied Chemistry, Kindai University, Higashi-Osaka, 577-8502, Japan.
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Organic Chemistry Department, Research Institute of Macroheterocycles, Ivanovo State University of Chemistry and Technology (ISUCT), Sheremetievskiy Av 7, Ivanovo, 153000, Russia.
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Schulich Faculty of Chemistry, Technion-Israel Institute of Technology, Haifa, 320003, Israel.
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