Synthesis and charge-carrier transport properties of poly(phosphole P-alkanesulfonylimide)s.

A new class of polyphospholes bearing alkanesulfonylimino moieties on the phosphorus(V) centers was prepared by the Pd-CuI-promoted Stille coupling reaction to investigate the charge-carrier transport properties of the π-networks of polyphospholes. Time-of-flight measurements have revealed that the poly(phosphole P-imide)s possess ambipolar charge-carrier mobilities of up to μ(electron) = 6 × 10(-3) cm(2) V(-1) s(-1) and μ(hole) = 4 × 10(-3) cm(2) V(-1) s(-1).

α,α'-Diarylacenaphtho[1,2-c]phosphole P-oxides: divergent synthesis and application to cathode buffer layers in organic photovoltaics.

A divergent method for the synthesis of α,α'-diarylacenaphtho[1,2-c]phosphole P-oxides has been established; α,α'-dibromoacenaphtho[c]phosphole P-oxide, which was prepared through a Ti(II)-mediated cyclization of 1,8-bis(trimethylsilylethynyl)naphthalene, underwent a Stille coupling with three different kinds of aryltributylstannanes to afford the α,α'-diarylacenaphtho[c]phosphole P-oxides in moderate to good yields. X-ray crystallographic analyses and UV/Vis absorption/fluorescence measurements have revealed that the degree of π-conjugation, the packing motif, the electron-accepting ability, and the thermal stability of the acenaphtho[c]phosphole π-systems are finely tunable with the α-aryl substituents. All the P=O and P=S derivatives exhibited high stability in their electrochemically reduced state.

Fusion of phosphole and 1,1'-biacenaphthene: phosphorus(V)-containing extended π-systems with high electron affinity and electron mobility.

A profusion of phospholes: Diacenaphtho[1,2-b:1',2'-d]phospholes, a new class of arene-fused phosphole π-systems, were synthesized and their structural and electrochemical properties studied. The P-sulfide derivative has a high electron-transporting ability (μ(E) =2.4×10(-3) cm(2) V(-1) s(-1)) in a vacuum-deposited film.

Synthesis of alpha,alpha'-linked oligophospholes and polyphospholes by using Pd-CuI-promoted Stille-type coupling.

Palladium-copper-promoted Stille-type cross-coupling reactions between alpha-stannylphospholes and alpha-iodophospholes afforded alpha,alpha'-linked oligophospholes and polyphosphole efficiently. It has been revealed that the polyphosphole P-oxide possesses an extremely narrow band gap and a high electron-accepting ability as compared to polythiophene.

Phosphole-triazole hybrids: a facile synthesis and complexation with Pd(II) and Pt(II) salts.

The copper-promoted Huisgen reaction of alpha-ethynylphosphole P-oxides with aryl azides affords alpha-(1-aryl-1,2,3-triazol-4-yl)phospholes in high yield. The alpha-(1-phenyl-1,2,3-triazol-4-yl)phosphole exhibits different coordination behavior in the complexation with MCl(2)(cod) (M = Pd, Pt). It has been revealed that P,N-coordination to PdCl(2) dramatically changes the optical properties of the newly constructed phosphole-triazole hybrid pi-system.