Adamantane substitutions: a path to high-performing, soluble, versatile and sustainable organic semiconducting materials

Novel ethyladamantyl solubilization side groups were found to induce π–π interactions between the conjugated cores through adamantyl–adamantyl stacking in soluble diketopyrrolopyrrole (DPP) derivatives. The closeness of the DPP cores amplifies charge transfer in the material, as far as the π–π interaction is a dominant charge-hopping pathway. As a result, tenfold enhancement of hole mobilities exceeding those obtained for insoluble derivatives was reached. Moreover, due to high crystallinity and co-planarity of the conjugated cores, electron transfer was preserved with a mobility of 0.2 cm2 V−1 s−1 for dithiophene-DPP. At the same time, the material remained soluble, which is a significant advantage for purification and processing. This approach can be universally applied for many types of semiconducting organic materials containing the imide motif, where solubilization is achieved by side-group substitution.

[1]  G. Garcia‐Belmonte,et al.  Recent Advances to Understand Morphology Stability of Organic Photovoltaics , 2016, Nano-Micro Letters.

[2]  R. Friend,et al.  Air-Stable n-channel Diketopyrrolopyrrole-Diketopyrrolopyrrole Oligomers for High Performance Ambipolar Organic Transistors. , 2016, ACS applied materials & interfaces.

[3]  N. S. Sariciftci,et al.  Hydrogen‐Bonded Organic Semiconductors as Stable Photoelectrocatalysts for Efficient Hydrogen Peroxide Photosynthesis , 2016 .

[4]  U. Schubert,et al.  Polymer-Based Organic Batteries. , 2016, Chemical reviews.

[5]  J. Faraudo,et al.  Observation and modeling of conformational molecular structures driving the self-assembly of tri-adamantyl benzene on Ag(111). , 2016, Physical chemistry chemical physics : PCCP.

[6]  J. Krajcovic,et al.  Adamantyl side groups boosting the efficiency and thermal stability of organic solid-state fluorescent dyes , 2016 .

[7]  B. Thompson,et al.  Random poly(3-hexylthiophene- co -3-cyanothiophene- co -3-(2-ethylhexyl)thiophene) copolymers with high open-circuit voltage in polymer solar cells , 2016 .

[8]  E. Katz,et al.  Efficient solar cells are more stable: The impact of polymer molecular weight on performance of organic photovoltaics , 2016 .

[9]  K. Müllen,et al.  Self-assembly and charge carrier transport of solution-processed conjugated polymer monolayers on dielectric surfaces with controlled sub-nanometer roughness. , 2016, Nanoscale.

[10]  Sang Kyu Lee,et al.  Synthesis and Photophysical Studies of Thiadiazole[3,4-c]pyridine Copolymer Based Organic Field-Effect Transistors , 2016, Journal of Fluorescence.

[11]  L. Fekete,et al.  Effect of the Side Chains and Anode Material on Thermal Stability and Performance of Bulk-Heterojunction Solar Cells Using DPP(TBFu)2 Derivatives as Donor Materials , 2015 .

[12]  Yiwang Chen,et al.  N-Type Alcohol-Soluble Small Molecules as an Interfacial Layer for Efficient and Stable Polymer Solar Cells , 2015 .

[13]  Amit Kumar,et al.  Utilization of simply alkylated diketopyrrolopyrrole derivative as a p-channel semiconductor for organic devices , 2015 .

[14]  I. Osaka,et al.  Highly Efficient and Stable Solar Cells Based on Thiazolothiazole and Naphthobisthiadiazole Copolymers , 2015, Scientific Reports.

[15]  Giuseppe Romanazzi,et al.  Epindolidiones—Versatile and Stable Hydrogen‐Bonded Pigments for Organic Field‐Effect Transistors and Light‐Emitting Diodes , 2015 .

[16]  A. McLean,et al.  Torsional angle dependence and switching of inner sphere reorganisation energies for electron and hole transfer processes involving phenyl substituted diketopyrrolopyrroles; a density functional study , 2015 .

[17]  Katherine A Mazzio,et al.  The future of organic photovoltaics. , 2015, Chemical Society reviews.

[18]  Joydeep Dhar,et al.  Herringbone to cofacial solid state packing via H-bonding in diketopyrrolopyrrole (DPP) based molecular crystals: influence on charge transport. , 2015, Chemical communications.

[19]  Alán Aspuru-Guzik,et al.  Hydrogen-bonded diketopyrrolopyrrole (DPP) pigments as organic semiconductors , 2014, Organic electronics.

[20]  Claudia Gollner,et al.  Hydrogen-Bonded Organic Semiconductor Micro- And Nanocrystals: From Colloidal Syntheses to (Opto-)Electronic Devices , 2014, Journal of the American Chemical Society.

[21]  U. Salzner,et al.  Use of side-chain for rational design of n-type diketopyrrolopyrrole-based conjugated polymers: what did we find out? , 2014, Physical chemistry chemical physics : PCCP.

[22]  J. Xue,et al.  Recent progress in organic photovoltaics: device architecture and optical design , 2014 .

[23]  Yang Yang,et al.  A Series of Squaraine Dyes: Effects of Side Chain and the Number of Hydroxyl Groups on Material Properties and Photovoltaic Performance , 2014 .

[24]  S. Mannsfeld,et al.  Side-Chain Engineering of Isoindigo-Containing Conjugated Polymers Using Polystyrene for High-Performance Bulk Heterojunction Solar Cells , 2013 .

[25]  Illhun Cho,et al.  High‐Mobility n‐Type Organic Transistors Based on a Crystallized Diketopyrrolopyrrole Derivative , 2013 .

[26]  Fabio Benfenati,et al.  Organic semiconductors for artificial vision. , 2013, Journal of materials chemistry. B.

[27]  Prashant Sonar,et al.  High mobility diketopyrrolopyrrole (DPP)-based organic semiconductor materials for organic thin film transistors and photovoltaics , 2013 .

[28]  Seung-Un Park,et al.  Non-functionalized soluble diketopyrrolopyrrole: Simplest p-channel core for organic field-effect transistors , 2013 .

[29]  Mihai Irimia-Vladu,et al.  Hydrogen‐Bonded Semiconducting Pigments for Air‐Stable Field‐Effect Transistors , 2013, Advanced materials.

[30]  N. S. Sariciftci,et al.  Optical and electrical properties of electrochemically doped organic field effect transistors , 2013, Journal of Luminescence.

[31]  S. Patil,et al.  Influence of Side-Chain on Structural Order and Photophysical Properties in Thiophene Based Diketopyrrolopyrroles: A Systematic Study , 2012 .

[32]  J. Wagner,et al.  Bipolar charge transport in organic field-effect transistors: Enabling high mobilities and transport of photo-generated charge carriers by a molecular passivation layer , 2012 .

[33]  N. Thejo Kalyani,et al.  Organic light emitting diodes: Energy saving lighting technology—A review , 2012 .

[34]  Mihai Irimia-Vladu,et al.  Indigo and Tyrian Purple – From Ancient Natural Dyes to Modern Organic Semiconductors , 2012 .

[35]  Daoben Zhu,et al.  Diketopyrrolopyrrole-containing quinoidal small molecules for high-performance, air-stable, and solution-processable n-channel organic field-effect transistors. , 2012, Journal of the American Chemical Society.

[36]  J. Vyňuchal,et al.  Absorption and fluorescence of soluble polar diketo-pyrrolo-pyrroles , 2011 .

[37]  Reinhard Schwödiauer,et al.  Anodized Aluminum Oxide Thin Films for Room‐Temperature‐Processed, Flexible, Low‐Voltage Organic Non‐Volatile Memory Elements with Excellent Charge Retention , 2011, Advanced materials.

[38]  S. Bauer,et al.  Ambipolar organic field effect transistors and inverters with the natural material Tyrian Purple , 2011 .

[39]  S. P. Tiwari,et al.  Vertically stacked complementary inverters with solution-processed organic semiconductors , 2011 .

[40]  J. Vyňuchal,et al.  Stability and structural aspects of diketopyrrolopyrrole pigment and its N-alkyl derivatives , 2011 .

[41]  F. Würthner,et al.  J-aggregates: from serendipitous discovery to supramolecular engineering of functional dye materials. , 2011, Angewandte Chemie.

[42]  A. Opitz,et al.  High-mobility copper-phthalocyanine field-effect transistors with tetratetracontane passivation layer and organic metal contacts , 2010 .

[43]  Petr Toman,et al.  Novel, soluble diphenyl-diketo-pyrrolopyrroles: Experimental and theoretical study , 2010 .

[44]  Zhenan Bao,et al.  Fabrication of low-cost electronic biosensors , 2009 .

[45]  J. Vyňuchal,et al.  Comparative Studies of Diphenyl-Diketo-Pyrrolopyrrole Derivatives for Electroluminescence Applications , 2008, Journal of Fluorescence.

[46]  P. Blom,et al.  Ambipolar charge transport in organic field-effect transistors , 2006 .

[47]  Richard H. Friend,et al.  General observation of n-type field-effect behaviour in organic semiconductors , 2005, Nature.

[48]  Marya Lieberman,et al.  Growth of Ultrasmooth Octadecyltrichlorosilane Self-Assembled Monolayers on SiO2 , 2003 .

[49]  S. Chen,et al.  Trap levels and effect of oxygen in poly[2-methoxy-5- (2′-ethyl-hexyloxy)-1,4-phenylene vinylene] diodes , 2002 .

[50]  M. Lohrengel,et al.  Thin anodic oxide layers on aluminium and other valve metals: high field regime , 1993 .

[51]  A. Becke.  Density-functional thermochemistry. III. The role of exact exchange , 1993 .

[52]  P. Schleyer,et al.  Adamantane: Consequences of the Diamondoid Structure , 1964 .