Self-Assembly Properties of Solution Processable, Electroactive Alkoxy, and Alkylthienylene Derivatives of Fused Benzoacridines: A Scanning Tunneling Microscopy Study

Tomasz Jaroch , Agnieszka Maranda-Niedbała , Klaudyna Krzyżewska , Kamil Kotwica , Piotr Bujak , Łukasz Skórka , Małgorzata Zagórska , Adam Proń , Robert Nowakowski

Abstract

Self-organization in mono- and bilayers on HOPG of two groups of benz[5,6]acridino[2,1,9,8-klmna]acridine derivatives, namely, 8,16-dialkoxybenzo[h]benz[5,6]acridino[2,1,9,8-klmna]acridines with an increasing alkoxy substituent length and 8,16-bis(3- or 4- or 5-octylthiophen-2-yl)benzo[h]benz[5,6]acridino[2,1,9,8-klmna]acridines, i.e., three positional isomers of the same benzoacridine, is investigated by scanning tunneling microscopy. The layers were deposited from a solution of the adsorbate (in hexane or dichloromethane) and imaged ex situ at molecular resolution. In all cases, the resulting two-dimensional (2D) supramolecular organization is governed by the interactions between large, fused heteroaromatic cores that form densely packed rows separated by areas covered by substituents. In 8,16-dialkoxybenzo[h]benz[5,6]acridino[2,1,9,8-klmna]acridines, the alkoxy substituents, separating the rows of densely packed cores, are interdigitated. An increasing substituent length leads to an intuitively expected increase in this 2D unit cell parameter that corresponds to the orientation of the substituent in the monolayer. In the case of 8,16-bis(3- or 4- or 5-octylthiophen-2-yl)benzo[h]benz[5,6]acridino[2,1,9,8-klmna]acridine positional isomers, the self-assembly processes are more complex. Although the determined 2D unit cell is in all cases essentially the same, the role of alkylthienylene substituents in layer formation is distinctly different. Thus, the formation of monolayers and bilayers is very sensitive to isomerism. 8,16-Bis(5-octylthiophen-2-yl)benzo[h]benz[5,6]acridino[2,1,9,8-klmna]acridine is capable of forming the most stable monolayer and the most labile bilayer. In the case of 8,16-bis(3-octylthiophen-2-yl)benzo[h]benz[5,6]acridino[2,1,9,8-klmna]acridine, an inverse phenomenon is observed leading to the most labile monolayer and the most stable bilayer. These differences are rationalized in terms of dissimilar molecular geometries of the studied isomers and different interdigitation patterns in their 2D supramolecular structures.

Author Tomasz Jaroch - Instytut Chemii Fizycznej PAN
Tomasz Jaroch,,
-
, Agnieszka Maranda-Niedbała - Instytut Chemii Fizycznej PAN
Agnieszka Maranda-Niedbała,,
-
, Klaudyna Krzyżewska - Instytut Chemii Fizycznej PAN
Klaudyna Krzyżewska,,
-
, Kamil Kotwica - Instytut Chemii Fizycznej PAN
Kamil Kotwica,,
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, Piotr Bujak (FC / CPCT)
Piotr Bujak,,
- Chair Of Polymer Chemistry And Technology
, Łukasz Skórka (FC / CPCT)
Łukasz Skórka,,
- Chair Of Polymer Chemistry And Technology
, Małgorzata Zagórska (FC / CPCT)
Małgorzata Zagórska,,
- Chair Of Polymer Chemistry And Technology
, Adam Proń (FC / CPCT)
Adam Proń,,
- 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,,
-
Journal seriesLangmuir, ISSN 0743-7463, e-ISSN 1520-5827
Issue year2020
Vol36
No19
Pages5417-5427
Publication size in sheets0.5
ASJC Classification1603 Electrochemistry; 1607 Spectroscopy; 2500 General Materials Science; 3104 Condensed Matter Physics; 3110 Surfaces and Interfaces
DOIDOI:10.1021/acs.langmuir.9b03966
URL https://pubs.acs.org/doi/10.1021/acs.langmuir.9b03966
Languageen angielski
File
acs.langmuir.9b03966.pdf 11.13 MB
Score (nominal)100
Score sourcejournalList
ScoreMinisterial score = 100.0, 03-08-2020, ArticleFromJournal
Publication indicators Scopus Citations = 0; Scopus SNIP (Source Normalised Impact per Paper): 2016 = 1.188; WoS Impact Factor: 2018 = 3.683 (2) - 2018=3.888 (5)
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