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Chem Rec. 2015 Jun;15(3):636-50. doi: 10.1002/tcr.201402101. Epub 2015 Mar 24.

Synthesis and Structure-Property Relationships of Phosphole-Based π Systems and Their Applications in Organic Solar Cells.

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Department of Chemistry, Faculty of Science, Niigata University, Nishi-ku, Niigata, 950-2181, Japan.


Phosphole is a chemically tunable heterole, and its π-conjugated derivatives are potential candidates for optoelectronic materials. This account describes recent developments in the synthesis and structure-property relationships of π-conjugated phosphole derivatives made by my research group. Thiophene-phosphole-styrene, phosphole-acetylene-arene, oligophosphole, polyphosphole, areno[c]phosphole, and phosphole-heterole π systems are synthesized using titanacycle-mediated metathesis and palladium-catalyzed cross-coupling reactions. The structural, optical, and electrochemical properties of selected compounds are discussed. Initial results on some applications of thiophene-phosphole copolymers, acenaphtho[c]phospholes, and amine-terthiophene-phosphole donor-π-acceptor dyes in organic solar cells are described. These results give valuable information and guidelines for designing new phosphorus-containing organic materials for molecular electronics.


heterocycles; materials science; organic solar cells; phospholes; polymers


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