Self-assembly properties of semiconducting donor-acceptor-donor bithienyl derivatives of tetrazine and thiadiazole - Effect of the electron accepting central ring

Joanna Zapala , M. Knor , T. Jaroch , A. Maranda-Niedbala , Ewa Kurach , Kamil Kotwica , Robert Nowakowski , D. Djurado , J. Pecaut , Małgorzata Zagórska , Adam Proń

Abstract

Scanning tunneling microscopy was used to study the effect of the electron-accepting unit and the alkyl substituent's position on the type and extent of 2D supramolecular organization of penta-ring donor-acceptor-donor (DAD) semiconductors, consisting of either tetrazine or thiadiazole central acceptor ring symmetrically attached to two bithienyl groups. Microscopic observations of monomolecular layers on HOPG of four alkyl derivatives of the studied adsorbates indicate significant differences in their 2D organizations. Ordered monolayers of thiadiazole derivatives are relatively loose and, independent of the position of alkyl substituents, characterized by large intermolecular separation of acceptor units in the adjacent molecules located in the face-to-face configuration. The 2D supramolecular architecture in both derivatives of thiadiazole is very sensitive to the alkyl substituent's position. Significantly different behavior is observed for derivatives of tetrazine (which is a stronger electron acceptor). Stronger intermolecular DA interactions in these adsorbates generate an intermolecular shift in the monolayer, which is a dominant factor determining the 2D structural organization. As a consequence of this molecular arrangement, tetrazine groups (A segments) face thiophene rings (D segments) of the neighboring molecules. Monolayers of tetrazine derivatives are therefore much more densely packed and characterized by similar π-stacking of molecules independently of the position of alkyl substituents. Moreover, a comparative study of 3D supramolecular organization, deduced from the X-ray diffraction patterns, is also presented clearly confirming the polymorphism of the studied adsorbates. © 2013 American Chemical Society.

Author Joanna Zapala - [Institute of Physical Chemistry of the Polish Academy of Sciences]
Joanna Zapala,,
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, M. Knor
M. Knor,,
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, T. Jaroch
T. Jaroch,,
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, A. Maranda-Niedbala
A. Maranda-Niedbala,,
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, Ewa Kurach (FC / CPCT)
Ewa Kurach,,
- Chair Of Polymer Chemistry And Technology
, Kamil Kotwica (FC / CPCT)
Kamil Kotwica,,
- Chair Of Polymer Chemistry And Technology
, Robert Nowakowski - Institute of Physical Chemistry Polish Academy of Sciences (IChF PAN) [Polish Academy of Sciences (PAN)]
Robert Nowakowski,,
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, D. Djurado
D. Djurado,,
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, J. Pecaut
J. Pecaut,,
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, Małgorzata Zagórska (FC / CPCT)
Małgorzata Zagórska,,
- Chair Of Polymer Chemistry And Technology
et al.`
Journal seriesLangmuir, ISSN 0743-7463
Issue year2013
Vol29
Pages14503-14511
ASJC Classification1603 Electrochemistry; 1607 Spectroscopy; 3110 Surfaces and Interfaces; 3104 Condensed Matter Physics; 2500 General Materials Science
DOIDOI:10.1021/la4034707
Languageen angielski
Score (nominal)35
Score sourcejournalList
ScoreMinisterial score = 35.0, 25-07-2020, ArticleFromJournal
Ministerial score (2013-2016) = 35.0, 25-07-2020, ArticleFromJournal
Publication indicators Scopus Citations = 14; WoS Citations = 14; GS Citations = 20.0; Scopus SNIP (Source Normalised Impact per Paper): 2014 = 1.391; WoS Impact Factor: 2013 = 4.384 (2) - 2013=4.489 (5)
Citation count*20 (2020-05-27)
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