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).

[1]  P. Pickup,et al.  Comparison of geometries and electronic structures of polyacetylene, polyborole, polycyclopentadiene, polypyrrole, polyfuran, polysilole, polyphosphole, polythiophene, polyselenophene and polytellurophene , 1998 .

[2]  Yoshiharu Sato,et al.  Benzo[b]phosphole sulfides. Highly electron-transporting and thermally stable molecular materials for organic semiconductor devices , 2009 .

[3]  M. Hissler,et al.  Linear organic π-conjugated systems featuring the heavy Group 14 and 15 elements , 2003 .

[4]  S. Tagawa,et al.  Charge-carrier dynamics in polythiophene films studied by in-situ measurement of flash-photolysis time-resolved microwave conductivity (FP-TRMC) and transient optical spectroscopy (TOS) , 2006 .

[5]  S. Tagawa,et al.  Hole Conduction along Molecular Wires: σ‐Bonded Silicon Versus π‐Bond‐Conjugated Carbon , 2002 .

[6]  A. Facchetti,et al.  A high-mobility electron-transporting polymer for printed transistors , 2009, Nature.

[7]  Henning Sirringhaus,et al.  Efficient charge injection from a high work function metal in high mobility n-type polymer field-effect transistors , 2010 .

[8]  Y. Matano,et al.  A convenient method for the synthesis of alpha-ethynylphospholes and modulation of their pi-conjugated systems. , 2009, Angewandte Chemie.

[9]  C. Alemán,et al.  Comparative theoretical study of heterocyclic conducting oligomers : Neutral and oxidized forms , 2007 .

[10]  L. Ricard,et al.  Toward Polyphospholes: Synthesis and Structure of an α‐Linked Quaterphosphole , 1994 .

[11]  Y. Matano,et al.  Comparative study on the structural, optical, and electrochemical properties of bithiophene-fused benzo[c]phospholes. , 2008, Chemistry.

[12]  T. Baumgartner,et al.  Organophosphorus π-Conjugated Materials , 2006 .

[13]  Samson A. Jenekhe,et al.  One-Dimensional Nanostructures of π-Conjugated Molecular Systems: Assembly, Properties, and Applications from Photovoltaics, Sensors, and Nanophotonics to Nanoelectronics† , 2011 .

[14]  Seiichi Tagawa,et al.  Dynamics of photogenerated charge carrier and morphology dependence in polythiophene films studied by in situ time-resolved microwave conductivity and transient absorption spectroscopy , 2007 .

[15]  Yasuaki Tokudome,et al.  Fusion of phosphole and 1,1'-biacenaphthene: phosphorus(V)-containing extended π-systems with high electron affinity and electron mobility. , 2011, Angewandte Chemie.

[16]  T. Baumgartner,et al.  Combining form with function--the dawn of phosphole-based functional materials. , 2012, Dalton transactions.

[17]  Maxim Shkunov,et al.  High ambipolar and balanced carrier mobility in regioregular poly(3-hexylthiophene) , 2004 .

[18]  Yoshiharu Sato,et al.  Benzophosphole oxide and sulfide for thermally stable cathode buffer layers in organic thin-film photovoltaic devices. , 2010, Chemistry, an Asian journal.

[19]  Y. Matano,et al.  Synthesis of alpha,alpha'-linked oligophospholes and polyphospholes by using Pd-CuI-promoted Stille-type coupling. , 2010, Organic letters.

[20]  S. Tagawa,et al.  Electrodeless Determination of Charge Carrier Mobility in Poly(3-hexylthiophene) Films Incorporating Perylenediimide as Photoconductivity Sensitizer and Spectroscopic Probe , 2008 .

[21]  F. Mathey Phospha-organic chemistry: panorama and perspectives. , 2003, Angewandte Chemie.

[22]  A. Facchetti,et al.  Aggregation in a high-mobility n-type low-bandgap copolymer with implications on semicrystalline morphology. , 2012, Journal of the American Chemical Society.

[23]  Y. Matano,et al.  α,α'-Diarylacenaphtho[1,2-c]phosphole P-oxides: divergent synthesis and application to cathode buffer layers in organic photovoltaics. , 2012, Chemistry, an Asian journal.

[24]  L. D. Quin The Continuing Development of the Chemistry of Phospholes , 2006 .

[25]  S. Tagawa,et al.  Increase in the mobility of photogenerated positive charge carriers in polythiophene. , 2005, The journal of physical chemistry. B.

[26]  Y. Matano,et al.  Design and synthesis of phosphole-based pi systems for novel organic materials. , 2009, Organic & biomolecular chemistry.

[27]  T. Aida,et al.  Comprehensive approach to intrinsic charge carrier mobility in conjugated organic molecules, macromolecules, and supramolecular architectures. , 2012, Accounts of chemical research.

[28]  Igor F. Perepichka,et al.  Handbook of Thiophene-Based Materials , 2009 .

[29]  A. Facchetti,et al.  Time-of-flight measurements and vertical transport in a high electron-mobility polymer , 2011 .

[30]  Jing Ma,et al.  A Time-Dependent DFT Study on Band Gaps and Effective Conjugation Lengths of Polyacetylene, Polyphenylene, Polypentafulvene, Polycyclopentadiene, Polypyrrole, Polyfuran, Polysilole, Polyphosphole, and Polythiophene , 2002 .

[31]  L. Ricard,et al.  New Complexes of Divalent Thulium with Substituted Phospholyl and Cyclopentadienyl Ligands , 2005 .

[32]  Gerwin H. Gelinck,et al.  The mobility and relaxation kinetics of charge carriers in molecular materials studied by means of pulse-radiolysis time-resolved microwave conductivity: dialkoxy-substituted phenylene-vinylene polymers , 2002 .

[33]  A. Facchetti,et al.  Bulk Electron Transport and Charge Injection in a High Mobility n‐Type Semiconducting Polymer , 2010, Advanced materials.

[34]  Y. Matano,et al.  Acenaphtho[1, 2-c]phosphole P-oxide: a phosphole-naphthalene pi-conjugated system with high electron mobility. , 2009, Chemistry.