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The benzo[<jats:italic>b<\/jats:italic>]phosphole\u2013benzo[<jats:italic>b<\/jats:italic>]thiophene and \u2010indole derivatives were further converted to P,X\u2010bridged terphenylenes (X=S, N) by a palladium\u2010catalyzed oxidative cycloaddition reaction with 4\u2010octyne through the C<jats:sub>\u03b2<\/jats:sub>\uf8ffH activation. X\u2010ray analyses of three compounds showed that the benzo[<jats:italic>b<\/jats:italic>]phosphole\u2010benzo[<jats:italic>b<\/jats:italic>]heterole derivatives have coplanar \u03c0 planes as a result of the effective conjugation through inter\u2010ring C\uf8ffC bonds. The \u03c0\u2013\u03c0* transition energies and redox potentials of the <jats:italic>cis<\/jats:italic> and <jats:italic>trans<\/jats:italic> isomers of bis(benzo[<jats:italic>b<\/jats:italic>]phosphole) <jats:italic>P<\/jats:italic>\u2010oxide are very close to each other, suggesting that their optical and electrochemical properties are little affected by the relative stereochemistry at the two phosphorus atoms. The optical properties of the benzo[<jats:italic>b<\/jats:italic>]phosphole\u2013benzo[<jats:italic>b<\/jats:italic>]heterole hybrids are highly dependent on the benzo[<jats:italic>b<\/jats:italic>]heterole subunits. Steady\u2010state UV\/Vis absorption\/fluorescence spectroscopy, fluorescence lifetime measurements, and theoretical calculations of the non\u2010fused and acetylene\u2010fused benzo[<jats:italic>b<\/jats:italic>]phosphole\u2013benzo[<jats:italic>b<\/jats:italic>]heterole \u03c0 systems revealed that their emissive excited states consist of two different conformers in rapid equilibrium.<\/jats:p>","DOI":"10.1002\/chem.201203047","type":"journal-article","created":{"date-parts":[[2012,11,9]],"date-time":"2012-11-09T13:12:04Z","timestamp":1352466724000},"page":"15972-15983","source":"Crossref","is-referenced-by-count":63,"title":["Synthesis and Structure\u2013Property Relationships of 2,2\u2032\u2010Bis(benzo[<i>b<\/i>]phosphole) and 2,2\u2032\u2010Benzo[<i>b<\/i>]phosphole\u2013Benzo[<i>b<\/i>]heterole Hybrid \u03c0 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