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Length-dependent self-assembly of oligothiophene derivatives in thin films

Published online by Cambridge University Press:  19 January 2011

Brian S. Rolczynski ,
Jodi M. Szarko ,
Byeongdu Lee ,
Joseph Strzalka ,
Jianchang Guo ,
Yongye Liang ,
Luping Yu  and
Lin X. Chen
Brian S. Rolczynski
Affiliation:
Department of Chemistry, Northwestern University, Evanston, Illinois 60208; Chemical Sciences and Engineering Division and Argonne National Laboratory, Argonne, Illinois 60439; and Argonne-Northwestern Solar Energy Research (ANSER) Center, Northwestern University, Evanston, Illinois 60208
Jodi M. Szarko
Affiliation:
Department of Chemistry, Northwestern University, Evanston, Illinois 60208; and Argonne-Northwestern Solar Energy Research (ANSER) Center, Northwestern University, Evanston, Illinois 60208
Byeongdu Lee
Affiliation:
X-ray Sciences Division, Argonne National Laboratory, Argonne, Illinois 60439
Joseph Strzalka
Affiliation:
X-ray Sciences Division, Argonne National Laboratory, Argonne, Illinois 60439
Jianchang Guo
Affiliation:
Chemical Sciences and Engineering Division and Argonne National Laboratory, Argonne, Illinois 60439; and Department of Chemistry and The James Franck Institute, The University of Chicago, Chicago, Illinois 60637
Yongye Liang
Affiliation:
Department of Chemistry and The James Franck Institute, The University of Chicago, Chicago, Illinois 60637
Luping Yu*
Affiliation:
Argonne-Northwestern Solar Energy Research (ANSER) Center, Northwestern University, Evanston, Illinois 60208; and Department of Chemistry and The James Franck Institute, The University of Chicago, Chicago, Illinois 60637
Lin X. Chen*
Affiliation:
Department of Chemistry, Northwestern University, Evanston, Illinois 60208; Chemical Sciences and Engineering Division and Argonne National Laboratory, Argonne, Illinois 60439; and Argonne-Northwestern Solar Energy Research (ANSER) Center, Northwestern University, Evanston, Illinois 60208
*
a)Address all correspondence to these authors. e-mail: lchen@anl.gov
b)e-mail: lupingyu@uchicago.edu
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Abstract

Thin-film aggregation characteristics of a series of oligothiophenes with a central thieno[3,4-b]thiophene ester unit and 4 (M5), 8 (M9), and 16 (M17) regioregular hexylthiophene units were investigated. These oligomers exhibited length-dependent self-assembly characteristics upon spin coating. M9 formed long fibers, while M5 and M17 formed random domains. Grazing incidence x-ray diffraction was performed to understand the reason for this length dependence. The M5 had a dominant ester–ester interaction that disrupted long-range order. The M9 morphology was due to a balance of orthogonal backbone and ester effects, which imposed long-range order on the M9 aggregates. Meanwhile, the M17 ester chain had a smaller relative contribution to packing and functioned as a molecular defect, disrupting long-range order. As a result, though the local self-assembly between monomers was very similar for the molecules, backbone length dependent changes in intermolecular forces dominated long-range structure. The analysis of self-assembly characteristics in these materials provides guidance in the design of organic conjugated materials for use in semiconductor devices.

Keywords

X-ray Diffraction (XRD)Self-AssemblyPolymer
Type
Reviews
Information
Journal of Materials Research , Volume 26 , Issue 2: Focus Issue: Self-Assembly and Directed Assembly of Advanced Materials , 28 January 2011 , pp. 296 - 305
Copyright
Copyright © Materials Research Society 2011

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