Naphthalene bisimides asymmetrically and symmetrically N-substituted with triarylamine - comparison of spectroscopic, electrochemical, electronic and self-assembly properties

Renata Rybakiewicz , Joanna Zapala , David Djurado , Robert Nowakowski , Petr Toman , Jiri Pfleger , Jean-Marie Verilhac , Małgorzata Zagórska , Adam Proń


Two semiconducting naphthalene bisimides were comparatively studied: NBI-(TAA)2, symmetrically N-substituted with triaryl amine and asymmetric NBI-TAA-Oc with triaryl amine and octyl N-substituents. Both compounds show very similar spectroscopic and redox properties but differ in their supramolecular organization. As evidenced by STM, in monolayers on HOPG they form ordered 2D structures, however of different packing patterns. NBI-(TAA)2 does not form ordered 3D structures, yielding amorphous thin films whereas films of NBI-TAA-Oc are highly crystalline. DFT calculations predict the ionization potential (IP) of 5.22 eV and 5.18 eV for NBI-TAA-Oc and NBI-(TAA)2, respectively, as well as the electron affinity values (EA) of -3.25 eV and -3.22 eV. These results are consistent with the cyclic voltammetry data which yield similar values of IP (5.20 eV and 5.19 eV) and somehow different values of EA (-3.80 eV and -3.83 eV). As judged from these data, both semiconductors should exhibit ambipolar behavior. Indeed, NBI-TAA-Oc is ambipolar, showing hole and electron mobilities of 4.5 [times] 10-5 cm2/(V s) and of 2.6 [times] 10-4 cm2/(V s), respectively, in the field effect transistor configuration. NBI-(TAA)2 is not ambipolar and yields field effect only in the p-channel configuration. This different behavior is rationalized on the basis of structural factors. © 2013 the Owner Societies.
Author Renata Rybakiewicz (FC / CPCT)
Renata Rybakiewicz,,
- Chair Of Polymer Chemistry And Technology
, Joanna Zapala - [Institute of Physical Chemistry of the Polish Academy of Sciences]
Joanna Zapala,,
, David Djurado - [Universite Grenoble Alpes (UGA)]
David Djurado,,
- Université Grenoble Alpes
, Robert Nowakowski - [Institute of Physical Chemistry of the Polish Academy of Sciences]
Robert Nowakowski,,
, Petr Toman - [Institute of Macromolecular Chemistry of the Academy of Sciences of the Czech Republic]
Petr Toman,,
, Jiri Pfleger - [Institute of Macromolecular Chemistry of the Academy of Sciences of the Czech Republic]
Jiri Pfleger,,
, 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 seriesPhysical Chemistry Chemical Physics, ISSN 1463-9076
Issue year2013
Publication size in sheets0.5
Keywords in EnglishNaphthalene bisimides
ASJC Classification1606 Physical and Theoretical Chemistry; 3100 General Physics and Astronomy
Languageen angielski
c2cp43505e.pdf 2.22 MB
Score (nominal)40
Score sourcejournalList
ScoreMinisterial score = 35.0, 25-07-2020, ArticleFromJournal
Ministerial score (2013-2016) = 40.0, 25-07-2020, ArticleFromJournal
Publication indicators WoS Citations = 10; Scopus Citations = 9; GS Citations = 11.0; Scopus SNIP (Source Normalised Impact per Paper): 2014 = 1.253; WoS Impact Factor: 2013 = 4.198 (2) - 2013=4.023 (5)
Citation count*12 (2020-09-15)
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