Pyrene end-capped oligothiophene derivatives for organic thin-film transistors and organic solar cells

We have demonstrated an efficient one-step synthesis of pyrene end-capped thiophene oligomers as active materials for organic thin-film transistors (OTFTs) and donor materials for organic solar cells (OSCs). In particular, the OTFT device based on 5,5′′-di(pyren-1-yl)-2,2′:5′,2′′-terthiophene (3s) exhibited a reasonable field effect mobility of 0.11 cm2 V−1 s−1, and a power conversion efficiency of 1.20% was achieved when 3s was used as active materials in OSCs. These pyrene end-capped thiophene oligomers are considered to be good organic semiconducting materials for OTFTs and OSCs.

[1]  P. Prasad,et al.  Tricyanofuran-based donor–acceptor type chromophores for bulk heterojunction organic solar cells , 2012 .

[2]  K. Ho,et al.  Pyrene-based organic dyes with thiophene containing π-linkers for dye-sensitized solar cells: optical, electrochemical and theoretical investigations. , 2011, Physical chemistry chemical physics : PCCP.

[3]  Qingfeng Dong,et al.  New amorphous small molecules—Synthesis, characterization and their application in bulk heterojunction solar cells , 2011 .

[4]  C. Adachi,et al.  Phenanthrene-functionalized 3,6-dithiophen-2-yl-2,5- dihydropyrrolo[3,4–c]pyrrole-1,4-diones as donor molecules for solution-processed organic photovoltaic cells , 2011 .

[5]  Klaus Müllen,et al.  Pyrene-based materials for organic electronics. , 2011, Chemical reviews.

[6]  K. Müllen,et al.  Asymmetric pyrene derivatives for organic field-effect transistors. , 2011, Chemical communications.

[7]  P. Bäuerle,et al.  A-D-A-D-A-type oligothiophenes for vacuum-deposited organic solar cells. , 2011, Organic letters.

[8]  S. H. Kim,et al.  A benzothiadiazole-based oligothiophene for vacuum-deposited organic photovoltaic cells , 2010 .

[9]  Timo Meyer-Friedrichsen,et al.  Quaterthiophene-based multipods as promising materials for solution-processible organic solar cells and field effect transistors , 2010 .

[10]  Changhee Lee,et al.  4,4′,4″-Tris(4-naphthalen-1-yl-phenyl)amine as a multifunctional material for organic light-emitting diodes, organic solar cells, and organic thin-film transistors , 2010 .

[11]  Jung-Pyo Hong,et al.  Naphtho[2,3,a]pyrene as an efficient multifunctional organic semiconductor for organic solar cells, organic light-emitting diodes, and organic thin-film transistors , 2010 .

[12]  Choongik Kim,et al.  Solution-processable low-molecular weight extended arylacetylenes: versatile p-type semiconductors for field-effect transistors and bulk heterojunction solar cells. , 2010, Journal of the American Chemical Society.

[13]  Jiyoung Kim,et al.  Solution processable donor materials based on thiophene and triphenylamine for bulk heterojunction solar cells , 2010 .

[14]  F. Spano.  The spectral signatures of Frenkel polarons in H- and J-aggregates. , 2010, Accounts of chemical research.

[15]  Jung-Pyo Hong,et al.  Solution-based direct growth of organic crystals on an active channel region for printable bottom-contact organic field-effect transistors. , 2009, Angewandte Chemie.

[16]  Kyoung Chul Ko,et al.  Enhancement of electrogenerated chemiluminescence and radical stability by peripheral multidonors on alkynylpyrene derivatives. , 2009, Angewandte Chemie.

[17]  Changhee Lee,et al.  Efficient Blue Organic Light-Emitting Diodes using Newly Developed Pyrene-Based Electron Transport Materials , 2009 .

[18]  Jung-Pyo Hong,et al.  Organic single-nanofiber transistors from organogels. , 2009, Chemical communications.

[19]  Jang‐Joo Kim,et al.  Organic thin-film transistors based on 2,6-bis(2-arylvinyl)anthracene: high-performance organic semiconductors , 2008 .

[20]  D. Y. Yoon,et al.  High-performance organic semiconductors for thin-film transistors based on 2,7-divinyl[1]benzothieno[3,2-b]benzothiophene , 2008 .

[21]  D. Y. Yoon,et al.  High-performance organic semiconductors for thin-film transistors based on 2,6-bis(2-thienylvinyl)anthracene , 2008 .

[22]  Jihoon Kang,et al.  Tuning of Ag work functions by self-assembled monolayers of aromatic thiols for an efficient hole injection for solution processed triisopropylsilylethynyl pentacene organic thin film transistors , 2008 .

[23]  Min-Jie Huang,et al.  The Photophysical Properties of Dipyrenylbenzenes and Their Application as Exceedingly Efficient Blue Emitters for Electroluminescent Devices , 2008 .

[24]  John E Anthony,et al.  The larger acenes: versatile organic semiconductors. , 2008, Angewandte Chemie.

[25]  G. Malliaras,et al.  Efficient solution-processed photovoltaic cells based on an anthradithiophene/fullerene blend. , 2007, Journal of the American Chemical Society.

[26]  J. Fréchet,et al.  Organic semiconducting oligomers for use in thin film transistors. , 2007, Chemical reviews.

[27]  Henning Sirringhaus,et al.  Electron and ambipolar transport in organic field-effect transistors. , 2007, Chemical reviews.

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

[29]  M. Muccini.  A bright future for organic field-effect transistors , 2006, Nature materials.

[30]  F. Fages,et al.  Synthesis and thin film electronic properties of two pyrene-substituted oligothiophene derivatives , 2006 .

[31]  Yang Yang,et al.  High-efficiency solution processable polymer photovoltaic cells by self-organization of polymer blends , 2005 .

[32]  Abhishek P. Kulkarni,et al.  Electron Transport Materials for Organic Light-Emitting Diodes , 2004 .

[33]  A. Okamoto,et al.  Pyrene-labeled base-discriminating fluorescent DNA probes for homogeneous SNP typing. , 2004, Journal of the American Chemical Society.

[34]  Stephen R. Forrest,et al.  Efficient bulk heterojunction photovoltaic cells using small-molecular-weight organic thin films , 2003, Nature.

[35]  Michael A. Haase,et al.  Pentacene-based radio-frequency identification circuitry , 2003 .

[36]  M. Stylianakis,et al.  Efficient bulk heterojunction devices based on phenylenevinylene small molecule and perylene–pyrene bisimide , 2010 .

[37]  J. Kenny,et al.  Novel Anthracene-Core Molecule for the Development of Efficient PCBM-Based Solar Cells , 2008 .

[38]  J. Fréchet,et al.  Polymer-fullerene composite solar cells. , 2008, Angewandte Chemie.