Effect of Molecular Structure of α,α′-Dialkylquaterthiophenes and Their Organosilicon Multipods on Ordering, Phase Behavior, and Charge Carrier Mobility

We report on bulk structures of a family of quaterthiophene (4T) derivatives with linear and branched end groups such as α,α′-dihexylquaterthiophene (Hex-4T-Hex), α,α′-didecyl-quaterthiophene (Dec-4T-Dec) and α,α′-bis(2-ethylhexyl)quaterthiophene (EH-4T-EH), tetramethyldisiloxane-based dimers D2-Und-4T-EH and D2-Und-4T-Hex, and carbosilane-siloxane-based tetramers D4-Und-4T-EH and D4-Und-4T-Hex. The dimers and tetramers contain undecylenic (Und) spacers between the disiloxane and 4T- units of the molecule. The impact of the molecular architecture on the bulk structure at different temperatures is addressed with X-ray diffraction and differential scanning calorimetry. For all of the studied quaterthiophene-containing organosilicon multipods the formation of 4T-crystal sublattice is observed. The alkyl periphery plays an important role in the molecular packing and thermal stability of the ordered phase. They can stabilize or destabilize the crystal phase, depending on their length and architecture. The quat...

[1]  S. Ponomarenko,et al.  Conjugated Organosilicon Materials for Organic Electronics and Photonics , 2011 .

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

[3]  I. Salzmann,et al.  Solution‐Processable Septithiophene Monolayer Transistor , 2012, Advanced materials.

[4]  S. Matsuda,et al.  Fabrication of Polyimide‐Blend Thin Films Containing Uniformly Oriented Silver Nanorods and Their Use as Flexible, Linear Polarizers , 2005 .

[5]  Chang-Qi Ma,et al.  Functional oligothiophenes: molecular design for multidimensional nanoarchitectures and their applications. , 2009, Chemical reviews.

[6]  Fred Wudl,et al.  Light‐Emitting Polythiophenes , 2005 .

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

[8]  N. N. Makarova,et al.  Mesomorphism, Polymorphism, and Semicrystalline Morphology of Poly(Di-n-propylsiloxane) , 2006 .

[9]  M. Möller,et al.  Self-organization of polybases neutralized with mesogenic wedge-shaped sulfonic acid molecules: an approach toward supramolecular cylinders. , 2006, Journal of the American Chemical Society.

[10]  A. Thierry,et al.  Structural characterisation of single crystals and thin films of α,ω-dihexylquaterthiophene , 2005 .

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

[12]  R. A. Laudise,et al.  Crystal Growth, Structure, and Electronic Band Structure of α‐4T Polymorphs , 1998 .

[13]  E. DiMasi,et al.  Thin Films of a Main-Chain Columnar Liquid Crystal: Studies of Structure, Phase Transitions, and Alignment , 2009 .

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

[15]  Y. Yoshida,et al.  Correlation of the number of thiophene units with structural order and carrier mobility in unsubstituted even- and odd-numbered alpha-oligothiophene films. , 2005, The journal of physical chemistry. B.

[16]  A. Mourran,et al.  Star-Shaped Oligothiophenes for Solution-Processible Organic Electronics: Flexible Aliphatic Spacers Approach , 2006 .

[17]  Hagen Klauk,et al.  Organic electronics : materials, manufacturing and applications , 2006 .

[18]  A. J. Lovinger,et al.  Phase behavior of α,ω-dihexyl-α-quaterthiophene and ordering on a textured substrate , 2003 .

[19]  Zhenan Bao,et al.  Organic Thin Film Transistors Based on Cyclohexyl-Substituted Organic Semiconductors , 2005 .

[20]  K. Landfester,et al.  Synthesis and self-organization of α,ω-substituted oligothiophenes with long, branched alkyl substituents , 2007 .

[21]  A. Elschner,et al.  Fine Tuning of Solid-State Properties of Septithiophenes by Tailoring the Substituents , 2010 .

[22]  Howard E. Katz,et al.  α,ω-Dihexylquaterthiophene: A Second Thin Film Single-Crystal Organic Semiconductor , 1998 .

[23]  M. Toney,et al.  Thin film transistors based on alkylphenyl quaterthiophenes: Structure and electrical transport properties , 2007 .

[24]  G. Ungar Thermotropic hexagonal phases in polymers: common features and classification , 1993 .

[25]  S. Ponomarenko,et al.  Synthesis and thermal behaviour of α,α′-didecyloligothiophenes , 2003 .

[26]  Gilles Horowitz,et al.  Dihexylquaterthiophene, A Two-Dimensional Liquid Crystal-like Organic Semiconductor with High Transport Properties† , 1998 .

[27]  Chang-Qi Ma,et al.  Solution‐Processed Bulk‐Heterojunction Solar Cells Based on Monodisperse Dendritic Oligothiophenes , 2008 .

[28]  Ullrich Scherf,et al.  Organic semiconductors for solution-processable field-effect transistors (OFETs). , 2008, Angewandte Chemie.

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

[30]  B. Servet,et al.  Molecular engineering of organic semiconductors: design of self-assembly properties in conjugated thiophene oligomers , 1993 .