Heteroarenes as high performance organic semiconductors.

The design, synthesis, and characterization of new organic semiconductors (OSCs) are important aspects for the development of next-generation optoelectronic devices. Structurally, organic semiconductors based on π-conjugated molecules can be easily modified via rational synthesis to tune multi-level self-assembled structures and discover novel chemical, optical, and electronic properties. Heteroarenes, which contain chalcogens and nitrogens in fused aromatic rings, are being developed as promising semiconducting materials for applications in a variety of electronic devices due to their outstanding optoelectronic properties. We highlight recent approaches toward realizing high performance p-channel field effect transistors based on linear heteroacenes and heteroatom annulated polycyclic aromatics (PAHs) as key functional components. These comprehensive, but carefully orchestrated approaches simultaneously address (i) practical synthesis, (ii) tunable self-assembled packing arrangement as well as (iii) high electronic performance.

[1]  Nazario Martin,et al.  Materials for organic solar cells: the C60/pi-conjugated oligomer approach. , 2005, Chemical Society reviews.

[2]  C. E. Klopfenstein,et al.  The insertion and extrusion of heterosulfur bridges. XIV. Synthesis of nitrotriphenyleno[1,12-bcd]thiophenes† , 1987 .

[3]  Jishan Wu,et al.  N-annulated perylene fused porphyrins with enhanced near-IR absorption and emission. , 2010, Organic letters.

[4]  Xinliang Feng,et al.  Columnar liquid crystalline bis-N-annulated quaterrylenes. , 2011, Chemical communications.

[5]  H. Sakurai,et al.  Structural elucidation of sumanene and generation of its benzylic anions. , 2005, Journal of the American Chemical Society.

[6]  Lei Wang,et al.  High‐Performance Organic Field‐Effect Transistors from Organic Single‐Crystal Microribbons Formed by a Solution Process , 2010, Advanced materials.

[7]  Daoben Zhu,et al.  High-performance transistor based on individual single-crystalline micrometer wire of perylo[1,12-b,c,d]thiophene. , 2007, Journal of the American Chemical Society.

[8]  A. Wakamiya,et al.  General synthesis of thiophene and selenophene-based heteroacenes. , 2005, Organic letters.

[9]  Sankar Subramanian,et al.  Chromophore fluorination enhances crystallization and stability of soluble anthradithiophene semiconductors. , 2008, Journal of the American Chemical Society.

[10]  A. Camerman,et al.  The crystal and molecular structure of perylene , 1964, Proceedings of the Royal Society of London. Series A. Mathematical and Physical Sciences.

[11]  Yunqi Liu,et al.  Anthra[2,3-b]benzo[d]thiophene: An Air-Stable Asymmetric Organic Semiconductor with High Mobility at Room Temperature , 2008 .

[12]  Guang-Jiu Zhao,et al.  Excited state electronic structures and photochemistry of heterocyclic annulated perylene (HAP) materials tuned by heteroatoms: S, Se, N, O, C, Si, and B. , 2009, The journal of physical chemistry. A.

[13]  Yongfang Li,et al.  Phenanthro[1,10,9,8-cdefg]carbazole-containing copolymer for high performance thin-film transistors and polymer solar cells , 2012 .

[14]  A. Rajca,et al.  Synthesis of dithieno[2,3-b:3',2'-d]thiophenes-building blocks for cross-conjugated beta-oligothiophenes. , 2006, The Journal of organic chemistry.

[15]  H. Matsui,et al.  Inkjet printing of single-crystal films , 2011, Nature.

[16]  Zhigang Shuai,et al.  Computational methods for design of organic materials with high charge mobility. , 2010, Chemical Society reviews.

[17]  W. Siebrand,et al.  Charge Transfer Spectra of Aromatic Hydrocarbon Crystals , 1983 .

[18]  John E Anthony,et al.  Functionalized acenes and heteroacenes for organic electronics. , 2006, Chemical reviews.

[19]  C. E. Klopfenstein,et al.  The insertion and extrusion of heterosulfur bridges. XVI. Synthesis of triphenyleno[1,12‐bcd:4,5‐b'c'd']dithiophene , 1989 .

[20]  B. Batlogg,et al.  Hole mobility in organic single crystals measured by a flip-crystal field-effect technique , 2004 .

[21]  Z. Bao,et al.  Synthetic chemistry for ultrapure, processable, and high-mobility organic transistor semiconductors. , 2001, Accounts of chemical research.

[22]  Jishan Wu,et al.  Bis-N-annulated quaterrylenebis(dicarboximide) as a new soluble and stable near-infrared dye. , 2009, Organic letters.

[23]  Jishan Wu,et al.  Anthracene-fused BODIPYs as near-infrared dyes with high photostability. , 2011, Organic letters.

[24]  J. Anthony,et al.  Isomerically pure syn-anthradithiophenes: synthesis, properties, and FET performance. , 2012, Organic letters.

[25]  Antonio Facchetti,et al.  Semiconductors for organic transistors , 2007 .

[26]  Isao Ikemoto,et al.  Photooxidation of the Evaporated Films of Polycyclic Aromatic Hydrocarbons Studied by X-Ray Photoelectron Spectroscopy , 1988 .

[27]  Adam J. Matzger,et al.  Synthesis and Structure of Fused α-Oligothiophenes with up to Seven Rings , 2005 .

[28]  R. Scholl,et al.  Abspaltung aromatisch gebundenen Wasserstoffs und Verknüpfung aromatischer Kerne durch Aluminiumchlorid , 1912 .

[29]  K. Takimiya,et al.  High-performance dinaphtho-thieno-thiophene single crystal field-effect transistors , 2009 .

[30]  Yunqi Liu,et al.  Synthesis, Characterization, and Field‐Effect Transistor Performance of Thieno[3,2‐b]thieno[2′,3′:4,5]thieno[2,3‐d]thiophene Derivatives , 2009, Advanced Functional Materials.

[31]  Younan Xia,et al.  Fabrication of field-effect transistors from hexathiapentacene single-crystal nanowires. , 2007, Nano letters.

[32]  S. Furukawa,et al.  Development of a sila-Friedel-Crafts reaction and its application to the synthesis of dibenzosilole derivatives. , 2009, Journal of the American Chemical Society.

[33]  Wenliang Wang,et al.  1,5,9-Triazacoronenes: a family of polycyclic heteroarenes synthesized by a threefold Pictet-Spengler reaction. , 2010, Angewandte Chemie.

[34]  Dongge Ma,et al.  Management of charges and excitons for high-performance white organic light-emitting diodes. , 2010, Chemical Society reviews.

[35]  J. Lawson,et al.  Synthesis of a bridged [18]annulene , 1973 .

[36]  Y. Aso,et al.  Application of flash vacuum pyrolysis to the synthesis of sulfur-containing heteroaromatic systems , 1999 .

[37]  Zhaohui Wang,et al.  Tri-N-annulated hexarylene: an approach to well-defined graphene nanoribbons with large dipoles. , 2010, Journal of the American Chemical Society.

[38]  C. Reese,et al.  Hexathiapentacene: structure, molecular packing, and thin-film transistors. , 2006, Journal of the American Chemical Society.

[39]  C. Rovira,et al.  Novel small molecules for organic field-effect transistors: towards processability and high performance. , 2008, Chemical Society reviews.

[40]  Thomas N Jackson,et al.  Organic field-effect transistors from solution-deposited functionalized acenes with mobilities as high as 1 cm2/V x s. , 2005, Journal of the American Chemical Society.

[41]  Shouke Yan,et al.  Solution-processed, high-performance nanoribbon transistors based on dithioperylene. , 2011, Journal of the American Chemical Society.

[42]  W. Hu,et al.  Single crystalline microribbons of perylo[1,12-b,c,d]selenophene for high performance transistors , 2009 .

[43]  Theo Siegrist,et al.  Synthesis, crystal structure, and transistor performance of tetracene derivatives. , 2004, Journal of the American Chemical Society.

[44]  P. Günter,et al.  Highly ordered thin films of a bis(dithienothiophene) derivative , 2007 .

[45]  Lin Li,et al.  A Densely and Uniformly Packed Organic Semiconductor Based on Annelated β‐Trithiophenes for High‐Performance Thin Film Transistors , 2009 .

[46]  J. J. Looker Mononitration of perylene. Preparation and structure proof of the 1 and 3 isomers , 1972 .

[47]  Martin Baumgarten,et al.  Dithieno[2,3‐d;2′,3′‐d′]benzo[1,2‐b;4,5‐b′]dithiophene (DTBDT) as Semiconductor for High‐Performance, Solution‐Processed Organic Field‐Effect Transistors , 2009 .

[48]  Fang Wang,et al.  A highly pi-stacked organic semiconductor for field-effect transistors based on linearly condensed pentathienoacene. , 2005, Journal of the American Chemical Society.

[49]  Zhaohui Wang,et al.  Bis-N-annulated quaterrylene: an approach to processable graphene nanoribbons. , 2009, Organic letters.

[50]  Itaru Osaka,et al.  Thienoacene‐Based Organic Semiconductors , 2011, Advanced materials.

[51]  Oana D. Jurchescu,et al.  Interface‐Controlled, High‐Mobility Organic Transistors , 2007 .

[52]  Lei Zhang,et al.  Synthesis, packing arrangement and transistor performance of dimers of dithienothiophenes , 2009 .

[53]  Jean-Luc Brédas,et al.  Charge transport in organic semiconductors. , 2007, Chemical reviews.

[54]  Koichi M. T. Yamada,et al.  Single-crystal field-effect transistors of benzoannulated fused oligothiophenes and oligoselenophenes , 2007 .

[55]  Torahiko Ando,et al.  Macromolecular electronic device: Field-effect transistor with a polythiophene thin film , 1986 .

[56]  Zhaohui Wang,et al.  Heteroatom-annulated perylenes: practical synthesis, photophysical properties, and solid-state packing arrangement. , 2008, The Journal of organic chemistry.

[57]  Hao Luo,et al.  Dibenzoannelated tetrathienoacene: synthesis, characterization, and applications in organic field-effect transistors. , 2012, Organic letters.

[58]  H. Wynberg,et al.  SYNTHESIS AND PROPERTIES OF SOME HETEROCIRCULENES , 1975 .

[59]  F. Rosei,et al.  Heterocirculenes as a new class of organic semiconductors. , 2008, Chemical communications.

[60]  S. Mannsfeld,et al.  Trialkylsilylethynyl-Functionalized Tetraceno[2,3-b]thiophene and Anthra[2,3-b]thiophene Organic Transistors , 2008 .

[61]  Giovanna Barbarella,et al.  The deformability of the thiophene ring: a key to the understanding of the conformational properties of oligo- and polythiophenes , 1993 .

[62]  L. Alcácer,et al.  Perylo[1,12-b,c,d]thiophene , 1997 .

[63]  V. Nenajdenko,et al.  "Sulflower": a new form of carbon sulfide. , 2006, Angewandte Chemie.

[64]  Daoben Zhu,et al.  Micro- and nanocrystals of organic semiconductors. , 2010, Accounts of chemical research.

[65]  N. Branda,et al.  A 'chemically-gated' photoresponsive compound as a visible detector for organophosphorus nerve agents. , 2011, Chemical communications.

[66]  John E. Anthony,et al.  Organic Single-Crystal Field-Effect Transistors of a Soluble Anthradithiophene , 2008 .

[67]  H. Sirringhaus,et al.  A Highly π-Stacked Organic Semiconductor for Thin Film Transistors Based on Fused Thiophenes , 1998 .

[68]  T. Swager,et al.  Conjugated polymer-based chemical sensors. , 2000, Chemical reviews.

[69]  G. Malliaras,et al.  Isomerically pure electron-deficient anthradithiophenes and their acceptor performance in polymer solar cells. , 2011, Chemical communications.

[70]  Y. Aso,et al.  Triphenyleno[1,12-bcd:4,5-b′c′d′:8,9-b″c″d″]trithiophene: the first bowl-shaped heteroaromatic , 1999 .

[71]  Toshihiro Okamoto,et al.  High-performance organic semiconductors: asymmetric linear acenes containing sulphur. , 2006, Journal of the American Chemical Society.

[72]  Daoben Zhu,et al.  High-Performance, Stable Organic Field-Effect Transistors Based on trans-1,2-(Dithieno[2,3-b:3′,2′-d]thiophene)ethene , 2009 .