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A series of acenaphthene species with a diisopropylphosphino group and a variety of bismuth functionalities in the peri positions were synthesized and fully characterized, including single-crystal X-ray diffraction. The majority of the reported species feature a relatively rare interpnictogen P-Bi bond. The series includes the phosphine-bismuthine Acenap(P i Pr 2 )(BiPh 2 ) ( 2 ; Acenap = acenaphthene-5,6-diyl), which was subjected to a fluorodearylation reaction to produce Acenap(P i Pr 2 )(BiPhX) ( 5 - 8 and 10 ; X = BF 4  -  , Cl, Br, I, SPh), displaying varying degrees of ionicity. The geminally bis(acenaphthyl)-substituted [Acenap(P i Pr 2 )] 2 BiPh ( 3 ) shows a large through-space coupling of 17.8 Hz, formally 8TS  J  PP . Coupling deformation density calculations confirm the double through-space coupling pathway, in which the P and Bi lone pairs mediate communication between the two 31 P nuclei. Several synthetic routes toward the phosphine-diiodobismuthine Acenap(P i Pr 2 )(BiI 2 ) ( 9 ) have been investigated; however, the purity of this, surprisingly thermally stable potential synthon, remains poor.

Phosphorus–Bismuth Peri-Substituted Acenaphthenes: A Synthetic, Structural, and Computational Study