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

被引:44
作者
Kovalenko, Alexander [1 ]
Yumusak, Cigdem [2 ]
Heinrichova, Patricie [1 ]
Stritesky, Stanislav [1 ]
Fekete, Ladislav [3 ]
Vala, Martin [1 ]
Weiter, Martin [1 ]
Sariciftci, Niyazi Serdar [2 ]
Krajcovic, Jozef [1 ]
机构
[1] Brno Univ Technol, Fac Chem, Mat Res Ctr, Purkynova 118, Brno, Czech Republic
[2] Johannes Kepler Univ Linz, Linz Inst Organ Solar Cells LIOS, Phys Chem, Altenbergerstr 69, A-4040 Linz, Austria
[3] Acad Sci Czech Republ, Vvi, Inst Phys, Slovance 2, CZ-18221 Prague 8, Czech Republic
关键词
FIELD-EFFECT TRANSISTORS; SIDE-CHAIN; CONJUGATED POLYMERS; SMALL MOLECULES; EFFICIENT; PIGMENTS; DIKETOPYRROLOPYRROLES; MONOLAYERS; TRANSPORT; ALUMINUM;
D O I
10.1039/c6tc05076j
中图分类号
T [工业技术];
学科分类号
08 ;
摘要
Novel ethyladamantyl solubilization side groups were found to induce pi-pi 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 pi-pi 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 cm(2) 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.
引用
收藏
页码:4716 / 4723
页数:8
相关论文
共 54 条
[1]   Synthesis and Photophysical Studies of Thiadiazole[3,4-c]pyridine Copolymer Based Organic Field-Effect Transistors [J].
Bathula, Chinna ;
Lee, Sang Kyu ;
Kalode, Pranav ;
Badgujar, Sachin ;
Belavagi, Ningaraddi S. ;
Khazi, Imtiyaz Ahmed M. ;
Kang, Youngjong .
JOURNAL OF FLUORESCENCE, 2016, 26 (03) :1045-1052
[2]   DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].
BECKE, AD .
JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652
[3]   Observation and modeling of conformational molecular structures driving the self-assembly of tri-adamantyl benzene on Ag(111) [J].
Calmettes, Bastien ;
Estrampes, Nicolas ;
Coudret, Christophe ;
Roussel, Thomas J. ;
Faraudo, Jordi ;
Coratger, Roland .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2016, 18 (30) :20281-20289
[4]   Torsional angle dependence and switching of inner sphere reorganisation energies for electron and hole transfer processes involving phenyl substituted diketopyrrolopyrroles; a density functional study [J].
Calvo-Castro, Jesus ;
McHugh, Callum J. ;
McLean, Andrew J. .
DYES AND PIGMENTS, 2015, 113 :609-617
[5]   Recent progress in organic photovoltaics: device architecture and optical design [J].
Cao, Weiran ;
Xue, Jiangeng .
ENERGY & ENVIRONMENTAL SCIENCE, 2014, 7 (07) :2123-2144
[6]   A Series of Squaraine Dyes: Effects of Side Chain and the Number of Hydroxyl Groups on Material Properties and Photovoltaic Performance [J].
Chen, Guo ;
Sasabe, Hisahiro ;
Sasaki, Yusuke ;
Katagiri, Hiroshi ;
Wang, Xiao-Feng ;
Sano, Takeshi ;
Hong, Ziruo ;
Yang, Yang ;
Kido, Junji .
CHEMISTRY OF MATERIALS, 2014, 26 (03) :1356-1364
[7]   General observation of n-type field-effect behaviour in organic semiconductors [J].
Chua, LL ;
Zaumseil, J ;
Chang, JF ;
Ou, ECW ;
Ho, PKH ;
Sirringhaus, H ;
Friend, RH .
NATURE, 2005, 434 (7030) :194-199
[8]  
Coatanea E., 2009, PRINTED ELECT NOW FU, P63
[9]   Stability and structural aspects of diketopyrrolopyrrole pigment and its N-alkyl derivatives [J].
David, Jan ;
Weiter, Martin ;
Vala, Martin ;
Vynuchal, Jan ;
Kucerik, Jiri .
DYES AND PIGMENTS, 2011, 89 (02) :137-143
[10]   Herringbone to cofacial solid state packing via H-bonding in diketopyrrolopyrrole (DPP) based molecular crystals: influence on charge transport [J].
Dhar, Joydeep ;
Karothu, Durga Prasad ;
Patil, Satish .
CHEMICAL COMMUNICATIONS, 2015, 51 (01) :97-100