The Versatile Thiophene: An Overview of Recent Research on Thiophene‐Based Materials

In the last few years, thiophene-based materials, which are semiconductor and fluorescent compounds, have become a highly interdisciplinary field of research, with diverse studies ranging from the fabrication of electronic and optoelectronic devices to the selective detection of biopolymers. This article presents a survey of the papers published in the last two years and concludes with the authors' views on future developments.

[1]  I. Kityk,et al.  Design and Synthesis of Ruthenium Oligothienylacetylide Complexes. New Materials for Acoustically Induced Nonlinear Optics , 2005 .

[2]  Michael A. Haase,et al.  Recent Progress in Organic Electronics: Materials, Devices, and Processes , 2004 .

[3]  L. Overman,et al.  Catalytic asymmetric intramolecular aminopalladation: enantioselective synthesis of vinyl-substituted 2-oxazolidinones, 2-imidazolidinones, and 2-pyrrolidinones. , 2002, Journal of the American Chemical Society.

[4]  E. Tedesco,et al.  Solid-state supramolecular organization, established directly from powder diffraction data, and photoluminescence efficiency of rigid-core oligothiophene-S,S-dioxides. , 2003, Journal of the American Chemical Society.

[5]  Tsutomu Yokozawa,et al.  Chain-growth polymerization for poly(3-hexylthiophene) with a defined molecular weight and a low polydispersity , 2004 .

[6]  P. Bäuerle,et al.  Synthesis of a silk-inspired peptide-oligothiophene conjugate. , 2004, Organic & biomolecular chemistry.

[7]  Jing Ma,et al.  Packing Structures and Packing Effects on Excitation Energies of Amorphous Phase Oligothiophenes , 2004 .

[8]  Ping Liu,et al.  High-performance semiconducting polythiophenes for organic thin-film transistors. , 2004, Journal of the American Chemical Society.

[9]  C. Botta,et al.  Electroluminescent poly(fluorene-co-thiophene-S, S-dioxide): synthesis, characterisation and structure-property relationships , 2003 .

[10]  E. Tedesco,et al.  Solid-State Conformation, Molecular Packing, and Electrical and Optical Properties of Processable β-Methylated Sexithiophenes , 1999 .

[11]  G. Barbarella,et al.  Synthesis, structure and cytotoxicity of trimethylsilyl oligothienylcarbaldehydes and their derivatives , 2001 .

[12]  Fabio Biscarini,et al.  Spatially correlated charge transport in organic thin film transistors. , 2004, Physical review letters.

[13]  B. Ballarin,et al.  Radical ions from 3,3''',3''''-tris(butylsulfanyl)- 2,2':5',2'':5'',2''',5''',2'''':5'''',2'''''-sexithiophene: an experimental and theoretical study of the p- and n-doped oligomer. , 2003, Chemphyschem : a European journal of chemical physics and physical chemistry.

[14]  A Paul Alivisatos,et al.  Employing end-functional polythiophene to control the morphology of nanocrystal-polymer composites in hybrid solar cells. , 2004, Journal of the American Chemical Society.

[15]  R. D. Mccullough,et al.  In‐Situ End‐Group Functionalization of Regioregular Poly(3‐alkylthiophene) Using the Grignard Metathesis Polymerization Method , 2004 .

[16]  B. Ong,et al.  Poly(3,3 -dialkylterthiophene)s: Room-temperature, solution-processed, high-mobility semiconductors for organic thin-film transistors , 2005 .

[17]  C. Frisbie,et al.  Organic Thin‐Film Transistors Based on Tolyl‐Substituted Oligothiophenes , 2004 .

[18]  E. W. Meijer,et al.  About Oligothiophene Self-Assembly: From Aggregation in Solution to Solid-State Nanostructures , 2004 .

[19]  E. W. Meijer,et al.  Pi-conjugated oligo-(p-phenylenevinylene) rosettes and their tubular self-assembly. , 2004, Angewandte Chemie.

[20]  Akira Suzuki,et al.  Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995–1998 , 1999 .

[21]  T. Swager,et al.  Charge-specific interactions in segmented conducting polymers: an approach to selective ionoresistive responses. , 2004, Angewandte Chemie.

[22]  E. Yashima,et al.  Electron-induced switching of the supramolecular chirality of optically active polythiophene aggregates. , 2002, Journal of the American Chemical Society.

[23]  Tobin J. Marks,et al.  n‐Type Building Blocks for Organic Electronics: A Homologous Family of Fluorocarbon‐Substituted Thiophene Oligomers with High Carrier Mobility , 2003 .

[24]  V. Fattori,et al.  Oligothiophene-S,S-dioxides as a class of electron-acceptor materials for organic photovoltaics , 2004 .

[25]  Anders Hallberg,et al.  Microwave-accelerated homogeneous catalysis in organic chemistry. , 2002, Accounts of chemical research.

[26]  D. Moses,et al.  Poly(3-hexylthiophene) field-effect transistors with high dielectric constant gate insulator , 2004 .

[27]  Yasuhiko Arakawa,et al.  Organic light-emitting diodes driven by pentacene-based thin-film transistors , 2003 .

[28]  E. Levillain,et al.  Planarized Star‐Shaped Oligothiophenes as a New Class of Organic Semiconductors for Heterojunction Solar Cells , 2003 .

[29]  R. Nolte,et al.  Electroformed giant vesicles from thiophene-containing rod-coil diblock copolymers , 2004 .

[30]  W. J. King,et al.  STUDIES IN THE THIOPHENE SERIES. V. WOLFF-KISHNER REDUCTIONS1, 2 , 1949 .

[31]  K. Nilsson,et al.  Twisting macromolecular chains: self-assembly of a chiral supermolecule from nonchiral polythiophene polyanions and random-coil synthetic peptides. , 2004, Proceedings of the National Academy of Sciences of the United States of America.

[32]  Fred Wudl,et al.  A red, green, and blue (RGB) polymeric electrochromic device (PECD): the dawning of the PECD era. , 2004, Angewandte Chemie.

[33]  R. Cingolani,et al.  Oligothiophene isothiocyanates as a new class of fluorescent markers for biopolymers. , 2001, Journal of the American Chemical Society.

[34]  Jenq-Neng Hwang,et al.  Multicolored Electrochromism in Polymers: Structures and Devices , 2004 .

[35]  Tomasz Kowalewski,et al.  Tuning the electrical conductivity and self-assembly of regioregular polythiophene by block copolymerization: nanowire morphologies in new di- and triblock copolymers. , 2002 .

[36]  R. Cingolani,et al.  Room‐Temperature Nanoimprint Lithography of Non‐thermoplastic Organic Films , 2004 .

[37]  Jie Cao,et al.  Solid-state packing of conjugated oligomers: from pi-stacks to the herringbone structure. , 2004, Journal of the American Chemical Society.

[38]  C. Kappe,et al.  Controlled microwave heating in modern organic synthesis. , 2004, Angewandte Chemie.

[39]  Richard D. McCullough,et al.  THE CHEMISTRY OF CONDUCTING POLYTHIOPHENES , 1998 .

[40]  E. Levillain,et al.  Planarized star-shaped oligothiophenes with enhanced pi-electron delocalization. , 2004, Organic letters.

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

[42]  G. Barbarella.  Oligothiophene isothiocyanates as fluorescent markers. , 2002, Chemistry.

[43]  Henning Sirringhaus,et al.  Enhanced Mobility of Poly(3-hexylthiophene) Transistors by Spin-Coating from High-Boiling-Point Solvents , 2004 .

[44]  J. Fréchet,et al.  Polythiophene containing thermally removable solubilizing groups enhances the interface and the performance of polymer-titania hybrid solar cells. , 2004, Journal of the American Chemical Society.

[45]  Zhenan Bao,et al.  Oligofluorene−Thiophene Derivatives as High-Performance Semiconductors for Organic Thin Film Transistors , 2003 .

[46]  John K. Stille,et al.  The Palladium‐Catalyzed Cross‐Coupling Reactions of Organotin Reagents with Organic Electrophiles [New Synthetic Methods (58)] , 1986 .

[47]  Electronic correlations in oligo-acene and -thiopene organic molecular crystals. , 2003, Physical review letters.

[48]  E. W. Meijer,et al.  Surface-controlled self-assembly of chiral sexithiophenes , 2004 .

[49]  M. Melucci,et al.  Solvent-free, microwave-assisted synthesis of thiophene oligomers via Suzuki coupling. , 2002, The Journal of organic chemistry.

[50]  F. Garnier.  ORGANIC-BASED ELECTRONICS A LA CARTE , 1999 .

[51]  O. Inganäs,et al.  Electrophosphorescence from substituted poly(thiophene) doped with iridium or platinum complex , 2004 .

[52]  O. Inganäs,et al.  Multicolor oligothiophene-based light-emitting diodes , 2001 .

[53]  M. Melucci,et al.  Solution-phase microwave-assisted synthesis of unsubstituted and modified alpha-quinque- and sexithiophenes. , 2004, The Journal of organic chemistry.

[54]  J. Brédas,et al.  Polaron pair versus bipolaron on oligothiophene chains: a theoretical study of the singlet and triplet states. , 2003, Chemphyschem : a European journal of chemical physics and physical chemistry.

[55]  Ifor D. W. Samuel,et al.  Tuning of emission color for blue dendrimer blend light-emitting diodes , 2004 .

[56]  Robert A. Street,et al.  Additive jet printing of polymer thin-film transistors , 2003 .

[57]  T. Swager,et al.  Conducting metallopolymers: the roles of molecular architecture and redox matching. , 2005, Chemical communications.

[58]  E. Yashima,et al.  Metal-induced supramolecualr chirality in an optically active polythiophene aggregate. , 2002, Chemistry.

[59]  M. Zambianchi,et al.  Conformational chirality of oligothiophenes in the solid state. X‐Ray structure of 3,4′,4″‐trimethyl‐2,2′:5′,2″‐terthiophene , 1994 .

[60]  J. Ziller,et al.  Dinitrogen reduction by TmII, DyII, and NdII with simple amide and aryloxide ligands. , 2003, Journal of the American Chemical Society.

[61]  Christine M. Micheel,et al.  Biological applications of colloidal nanocrystals , 2003 .

[62]  Ute Zschieschang,et al.  High-mobility organic thin-film transistors based on α,α′-didecyloligothiophenes , 2003 .

[63]  N. F. Badham.  Homologation of Ketones into Carboxylic Acids , 2004 .

[64]  A. Zanelli,et al.  New Branched Thiophene‐Based Oligomers for Bright Organic Light‐Emitting Devices , 2003 .

[65]  P. Maccagnani,et al.  FET device performance, morphology and X-ray thin film structure of unsubstituted and modified quinquethiophenes , 2004 .

[66]  A. Katritzky,et al.  To what extent can aromaticity be defined uniquely? , 2002, The Journal of organic chemistry.

[67]  Tomasz Kowalewski,et al.  Tuning the electrical conductivity and self-assembly of regioregular polythiophene by block copolymerization: nanowire morphologies in new di- and triblock copolymers. , 2002, Angewandte Chemie.

[68]  Niyazi Serdar Sariciftci,et al.  Effects of Postproduction Treatment on Plastic Solar Cells , 2003 .

[69]  Y. Shirota.  Organic materials for electronic and optoelectronic devices , 2000 .

[70]  S. Stahl,et al.  "Inverse-electron-demand" ligand substitution in palladium(0)-olefin complexes. , 2003, Journal of the American Chemical Society.

[71]  C. Frisbie,et al.  Field effect transport and trapping in regioregular polythiophene nanofibers , 2004 .

[72]  Mats Andersson,et al.  Substituted polythiophenes designed for optoelectronic devices and conductors , 1999 .

[73]  G. Gigli,et al.  Poly(α-vinyl-ω-alkyloligothiophene) Side-Chain Polymers. Synthesis, Fluorescence, and Morphology , 2004 .

[74]  A. Alivisatos,et al.  Hybrid Nanorod-Polymer Solar Cells , 2002, Science.

[75]  Fred Wudl,et al.  Red, Green, and Blue Colors in Polymeric Electrochromics , 2004 .

[76]  Pablo Espinet,et al.  The mechanisms of the Stille reaction. , 2004, Angewandte Chemie.

[77]  C. Dimitrakopoulos,et al.  Organic Thin Film Transistors for Large Area Electronics , 2002 .

[78]  A. Heeger,et al.  A Novel Series of Efficient Thiophene-Based Light-Emitting Conjugated Polymers and Application in Polymer Light-Emitting Diodes , 2000 .

[79]  James R. Sheats,et al.  Manufacturing and commercialization issues in organic electronics , 2004 .

[80]  H. Shim,et al.  Synthesis, Characterization, and Electroluminescence of New Conjugated Polyfluorene Derivatives Containing Various Dyes as Comonomers , 2004 .

[81]  E. Ortí,et al.  The low-lying excited states of 2,2'-bithiophene: a theoretical analysis. , 2003, Chemphyschem : a European journal of chemical physics and physical chemistry.

[82]  J. Reynolds,et al.  High‐Quality Electrochromic Polythiophenes via BF3·Et2O Electropolymerization , 2003 .

[83]  Stephen R. Forrest,et al.  White Organic Light‐Emitting Devices for Solid‐State Lighting , 2004 .

[84]  R. Nolte,et al.  Vesicles and polymerized vesicles from thiophene-containing rod-coil block copolymers. , 2003, Angewandte Chemie.

[85]  Michele Muccini,et al.  Ambipolar light-emitting organic field-effect transistor , 2004 .

[86]  W. Fix,et al.  Influence of intensive light exposure on polymer field-effect transistors , 2004 .

[87]  P. Maccagnani,et al.  Multiscale Self-Organization of the Organic Semiconductor α-Quinquethiophene , 2003 .

[88]  R. Cingolani,et al.  Modes interaction and light transport in bidimensional organic random lasers in the weak scattering limit , 2004 .

[89]  G. Gigli,et al.  High-efficiency oligothiopene-based light-emitting diodes , 1999 .

[90]  Guillermo C. Bazan,et al.  Homogeneous Fluorescence-Based DNA Detection with Water-Soluble Conjugated Polymers , 2004 .

[91]  Ullrich Mitschke,et al.  The electroluminescence of organic materials , 2000 .

[92]  Kent R. Mann,et al.  High Electron Mobility and Ambipolar Transport in Organic Thin‐Film Transistors Based on a π‐Stacking Quinoidal Terthiophene , 2003 .

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

[94]  Geneviève Sauvé,et al.  Regioregular poly(thiophene-3-alkanoic acid)s: water soluble conducting polymers suitable for chromatic chemosensing in solution and solid state , 2004 .

[95]  Vivek Subramanian,et al.  Organic thin film transistors from a soluble oligothiophene derivative containing thermally removable solubilizing groups. , 2004, Journal of the American Chemical Society.

[96]  M. Lemaire,et al.  Aryl-aryl bond formation one century after the discovery of the Ullmann reaction. , 2002, Chemical reviews.

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

[98]  M. Boissinot,et al.  Fluorescent polymeric transducer for the rapid, simple, and specific detection of nucleic acids at the zeptomole level. , 2004, Journal of the American Chemical Society.

[99]  D. Braga,et al.  Solid State Conformation and Crystal Packing of Methyl-Substituted Quaterthiophenes , 2000 .

[100]  M. Durstock,et al.  An Investigation of Poly(thienylene vinylene) in Organic Photovoltaic Devices , 2004 .

[101]  Jean M. J. Fréchet,et al.  Controlling the Field‐Effect Mobility of Regioregular Polythiophene by Changing the Molecular Weight , 2003 .

[102]  U. Scherf,et al.  Semiconducting Polymers via Microwave‐Assisted Suzuki and Stille Cross‐Coupling Reactions , 2004 .

[103]  G. Barbarella,et al.  Conformational profile, energy barriers and optical properties of quinquethiophene-S,S-dioxides , 2002 .

[104]  Tony J. You,et al.  Discovery, modeling, and human pharmacokinetics of N-(2-acetyl-4,6-dimethylphenyl)-3-(3,4-dimethylisoxazol-5-ylsulfamoyl)thiophene-2-carboxamide (TBC3711), a second generation, ETA selective, and orally bioavailable endothelin antagonist. , 2004, Journal of medicinal chemistry.

[105]  A Paul Alivisatos,et al.  Room-temperature single-nucleotide polymorphism and multiallele DNA detection using fluorescent nanocrystals and microarrays. , 2003, Analytical chemistry.

[106]  R. Cingolani,et al.  Far-field emission and feedback origin of random lasing in oligothiophene dioxide neat films , 2003 .

[107]  Jiann T. Lin,et al.  Amorphous 2,3-Substituted Thiophenes: Potential Electroluminescent Materials , 2002 .

[108]  R. Advíncula,et al.  Characterization, supramolecular assembly, and nanostructures of thiophene dendrimers. , 2004, Journal of the American Chemical Society.

[109]  R. Cingolani,et al.  Tuning Solid-State Photoluminescence Frequencies and Efficiencies of Oligomers Containing One Central Thiophene-S,S-dioxide Unit , 2000 .

[110]  M. Leclerc,et al.  Affinitychromic polythiophenes: A novel bio-photonic tool for high-throughput screening and diagnostics , 2004 .

[111]  C. Winder,et al.  Low bandgap polymers for photon harvesting in bulk heterojunction solar cells , 2004 .

[112]  D. Bradley,et al.  Organic Photovoltaic Devices Based on Blends of Regioregular Poly(3-hexylthiophene) and Poly(9,9-dioctylfluorene-co-benzothiadiazole) , 2004 .

[113]  Gilles Horowitz,et al.  Organic thin film transistors: From theory to real devices , 2004 .

[114]  A. Elschner,et al.  Star‐Shaped Oligothiophenes for Solution‐Processible Organic Field‐Effect Transistors , 2003 .

[115]  Fred Wudl,et al.  Facile solid-state synthesis of highly conducting poly(ethylenedioxythiophene). , 2003, Angewandte Chemie.

[116]  E. Tedesco,et al.  Molecular Packing and Photoluminescence Efficiency in Odd-Membered Oligothiophene S,S-Dioxides , 2000 .

[117]  M. Berggren,et al.  1 micron wavelength photo- and electroluminescence from a conjugated polymer , 2004 .

[118]  T. Swager,et al.  A proton-doped calix[4]arene-based conducting polymer. , 2003, Journal of the American Chemical Society.

[119]  K. Nilsson,et al.  Synthesis of a regioregular zwitterionic conjugated oligoelectrolyte, usable as an optical probe for detection of amyloid fibril formation at acidic pH. , 2005, Journal of the American Chemical Society.

[120]  M. Leclerc,et al.  New colorimetric and fluorometric chemosensor based on a cationic polythiophene derivative for iodide-specific detection. , 2003, Journal of the American Chemical Society.

[121]  Ute Zschieschang,et al.  Relationship Between Molecular Structure and Electrical Performance of Oligothiophene Organic Thin Film Transistors , 2003 .

[122]  G. Gigli,et al.  Bright White Organic Light‐Emitting Devices from a Single Active Molecular Material , 2005 .

[123]  Bruno Jousselme,et al.  Crown-annelated oligothiophenes as model compounds for molecular actuation. , 2003, Journal of the American Chemical Society.

[124]  A. Bottoni,et al.  A Theoretical Investigation of the Torsional Potential in 3,3‘-Dimethyl-2,2‘-bithiophene and 3,4‘-Dimethyl-2,2‘-bithiophene: A Comparison between HF, MP2, and DFT Theory , 1999 .

[125]  H. Sirringhaus,et al.  Integrated optoelectronic devices based on conjugated polymers , 1998, Science.