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Title: Correlating Molecular Design to Microstructure in Thermally Convertible Oligothiophenes: The Effect of Branched Versus Linear End Groups

Abstract

The thin film microstructure development of functionalized oligothiophenes with branched, thermally removable groups at each end of conjugated cores with five, six, and seven thiophene rings was monitored during their thermal conversion from solution processible precursors to insoluble semiconductor products. The change in end group character provides a comparison of branched vs. linear end group functionalization in oligothiophenes. Near edge X-ray absorption fine structure (NEXAFS) spectroscopy confirmed that branched {alpha}-, {omega}-substitutions of the precursors strongly influenced the packing of the conjugated core. The quinque- and sexithiophene precursors oriented perpendicular to the substrate, whereas the septithiophene precursor oriented parallel to the substrate, providing one of the first examples of length dependence in oligothiophene orientation. This dependence may be due to a packing mismatch between the conjugated cores and the branched end groups. The convertible septithiophene exhibits four distinct microstructures as it converts from precursor to product that correlate strongly with its field-effect hole mobility in field-effect transistors. The extent of septithiophene order and the surface-relative orientation of its ordered phases clearly influence field-effect transistor performance.

Authors:
; ; ; ; ; ; ;
Publication Date:
Research Org.:
Brookhaven National Lab. (BNL), Upton, NY (United States). National Synchrotron Light Source
Sponsoring Org.:
Doe - Office Of Science
OSTI Identifier:
913957
Report Number(s):
BNL-78525-2007-JA
Journal ID: ISSN 1089-5647; JPCBFK; TRN: US200804%%303
DOE Contract Number:  
DE-AC02-98CH10886
Resource Type:
Journal Article
Journal Name:
J. Phys. Chem. B
Additional Journal Information:
Journal Volume: 110; Journal ID: ISSN 1089-5647
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE; POLYCYCLIC SULFUR HETEROCYCLES; MOLECULAR STRUCTURE; MICROSTRUCTURE; CORRELATIONS; THIN FILMS; SEMICONDUCTOR MATERIALS; FIELD EFFECT TRANSISTORS; HOLE MOBILITY; national synchrotron light source

Citation Formats

DeLongchamp, D, Jung, Y, Fischer, D, Lin, E, Chang, P, Subramanian, V, Murphy, A, and Frechet, J. Correlating Molecular Design to Microstructure in Thermally Convertible Oligothiophenes: The Effect of Branched Versus Linear End Groups. United States: N. p., 2006. Web. doi:10.1021/jp060667t.
DeLongchamp, D, Jung, Y, Fischer, D, Lin, E, Chang, P, Subramanian, V, Murphy, A, & Frechet, J. Correlating Molecular Design to Microstructure in Thermally Convertible Oligothiophenes: The Effect of Branched Versus Linear End Groups. United States. https://doi.org/10.1021/jp060667t
DeLongchamp, D, Jung, Y, Fischer, D, Lin, E, Chang, P, Subramanian, V, Murphy, A, and Frechet, J. 2006. "Correlating Molecular Design to Microstructure in Thermally Convertible Oligothiophenes: The Effect of Branched Versus Linear End Groups". United States. https://doi.org/10.1021/jp060667t.
@article{osti_913957,
title = {Correlating Molecular Design to Microstructure in Thermally Convertible Oligothiophenes: The Effect of Branched Versus Linear End Groups},
author = {DeLongchamp, D and Jung, Y and Fischer, D and Lin, E and Chang, P and Subramanian, V and Murphy, A and Frechet, J},
abstractNote = {The thin film microstructure development of functionalized oligothiophenes with branched, thermally removable groups at each end of conjugated cores with five, six, and seven thiophene rings was monitored during their thermal conversion from solution processible precursors to insoluble semiconductor products. The change in end group character provides a comparison of branched vs. linear end group functionalization in oligothiophenes. Near edge X-ray absorption fine structure (NEXAFS) spectroscopy confirmed that branched {alpha}-, {omega}-substitutions of the precursors strongly influenced the packing of the conjugated core. The quinque- and sexithiophene precursors oriented perpendicular to the substrate, whereas the septithiophene precursor oriented parallel to the substrate, providing one of the first examples of length dependence in oligothiophene orientation. This dependence may be due to a packing mismatch between the conjugated cores and the branched end groups. The convertible septithiophene exhibits four distinct microstructures as it converts from precursor to product that correlate strongly with its field-effect hole mobility in field-effect transistors. The extent of septithiophene order and the surface-relative orientation of its ordered phases clearly influence field-effect transistor performance.},
doi = {10.1021/jp060667t},
url = {https://www.osti.gov/biblio/913957}, journal = {J. Phys. Chem. B},
issn = {1089-5647},
number = ,
volume = 110,
place = {United States},
year = {Sun Jan 01 00:00:00 EST 2006},
month = {Sun Jan 01 00:00:00 EST 2006}
}