Arylene bisimides with triarylamine N-substituents as new solution processable organic semiconductors: Synthesis, spectroscopic, electrochemical and electronic properties

Renata Rybakiewicz , David Djurado , Hubert Cybulski , Ewelina Dobrzynska , Irena Kulszewicz-Bajer , Damien Boudinet , Jean-Marie Verilhac , Małgorzata Zagórska , Adam Proń


New solution processable organic semiconductors, consisting of pyrromelitic, naphthalene or perylene bisimide core and triarylamine N-substituents, have been synthesized. All three compounds are electrochemically active and undergo quasi-reversible oxidation and reduction as evidenced by cyclic voltammetry investigations. The oxidation process involves the transformation of the triarylamine substituents into radical cations as proven spectroscopically and spectroelectrochemically. The reduction process occurs at the arylene bisimide core leading to the formation of a radical anion and eventually a dianion in the second step. These findings are in perfect agreement with the DFT calculations which show that in the synthesized molecules the HOMO orbital is located on the triarylamine moiety whereas the LUMO one on the bisimide core. In all molecules studied the electrochemically determined ionization potential (IP) is slightly higher than 5.0 eV whereas in naphthalene and perylene derivatives the electron affinity (EA) is close to −3.9 eV. These values fulfill the requirements for n-type (electron) semiconductors in air operating n-channel field effect transistors (FETs) as well as for p-type (hole) conductors in p-channel FETs. To verify whether the newly synthesized compounds exhibit the expected electrical transport properties all organic (CYTOP dielectric) test transistors were fabricated. All three semiconductors showed no field effect in the n-channel configuration. To the contrary, they could be used in p-channel FETs showing, in the saturation regime, the hole mobility approaching 10−4 cm2 V−1 s−1 – the value which slightly exceeds that measured for low molecular weight, amorphous triarylamine semiconductors.
Author Renata Rybakiewicz - [Warsaw University of Technology (PW), MNiSW [80]]
Renata Rybakiewicz,,
- Politechnika Warszawska
, David Djurado - [Universite Grenoble Alpes (UGA)]
David Djurado,,
- Université Grenoble Alpes
, Hubert Cybulski - [Universidad de Santiago de Compostela]
Hubert Cybulski,,
, Ewelina Dobrzynska - [Politechnika Warszawska]
Ewelina Dobrzynska,,
, Irena Kulszewicz-Bajer (FC / CPCT)
Irena Kulszewicz-Bajer,,
- Chair Of Polymer Chemistry And Technology
, Damien Boudinet - [CEA Grenoble]
Damien Boudinet,,
, Jean-Marie Verilhac - [CEA Grenoble]
Jean-Marie Verilhac,,
, Małgorzata Zagórska (FC / CPCT)
Małgorzata Zagórska,,
- Chair Of Polymer Chemistry And Technology
, Adam Proń (FC / CPCT)
Adam Proń,,
- Chair Of Polymer Chemistry And Technology
Journal seriesSynthetic Metals, ISSN 0379-6779, (A 30 pkt)
Issue year2011
Keywords in EnglishArylene bisimides, DFT calculations, Low band semiconductors, Organic transistors, Triarylamine derivatives
ASJC Classification2505 Materials Chemistry; 2506 Metals and Alloys; 2210 Mechanical Engineering; 2211 Mechanics of Materials; 3104 Condensed Matter Physics; 2504 Electronic, Optical and Magnetic Materials
Score (nominal)30
Score sourcejournalList
Publication indicators Scopus Citations = 17; WoS Citations = 19; GS Citations = 24.0; Scopus SNIP (Source Normalised Impact per Paper): 2014 = 0.943; WoS Impact Factor: 2011 = 1.829 (2) - 2011=2.081 (5)
Citation count*24 (2020-01-31)
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* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.
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