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Title: Contorted Octabenzocircumbiphenyl Sorts Semiconducting Single-Walled Carbon Nanotubes with Structural Specificity

Abstract

Here, we use a nonplanar aromatic molecule, contorted octabenzocircumbiphenyl (c-OBCB), to sort semiconducting single-walled carbon nanotubes (SWNTs) by their chiral angles. From absorption spectroscopy, photoluminescence excitation spectroscopy, and Raman spectroscopy studies, we find that c-OBCB preferentially binds and sorts for a number of semiconducting carbon nanotubes with chiral angles greater than 12°. Molecular dynamics simulations reveal that the contorted aromatic core of c-OBCB binds strongly to only certain SWNTs, especially those with matching curvature, and that this discriminatory binding interaction is reinforced by preferences of the side chains on the c-OBCB to stick to SWNT surface rather than interact with the solvent. This opens the door to side chain/solvent engineering to bias the selection of certain (m,n) SWNT variants. We also investigate the temperature dependence of hole mobility in field-effect transistors comprising c-OBCB-sorted semiconducting carbon-nanotube networks and find hole transport in these networks to be thermally activated.

Authors:
 [1];  [2];  [3];  [3]; ORCiD logo [3]; ORCiD logo [2]; ORCiD logo [1]
  1. Princeton Univ., NJ (United States)
  2. Cornell Univ., Ithaca, NY (United States)
  3. Columbia Univ., New York, NY (United States)
Publication Date:
Research Org.:
Columbia Univ., New York, NY (United States)
Sponsoring Org.:
USDOE Office of Science (SC); Netherlands Organization for Scientific Research (NWO); National Science Foundation (NSF); USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division
OSTI Identifier:
1534447
Grant/Contract Number:  
FG02-01ER15264; 680-50-1202; CHE-1124754; CMMI-1537011
Resource Type:
Accepted Manuscript
Journal Name:
Chemistry of Materials
Additional Journal Information:
Journal Volume: 29; Journal Issue: 2; Journal ID: ISSN 0897-4756
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 36 MATERIALS SCIENCE; Chemistry; Materials science; Thickness; Charge transport; Carbon nanotubes; Mathematical methods; Selectivity

Citation Formats

Gao, Jia, Sengar, Nikita, Wu, Ying, Jockusch, Steffen, Nuckolls, Colin, Clancy, Paulette, and Loo, Yueh-Lin. Contorted Octabenzocircumbiphenyl Sorts Semiconducting Single-Walled Carbon Nanotubes with Structural Specificity. United States: N. p., 2017. Web. doi:10.1021/acs.chemmater.6b04018.
Gao, Jia, Sengar, Nikita, Wu, Ying, Jockusch, Steffen, Nuckolls, Colin, Clancy, Paulette, & Loo, Yueh-Lin. Contorted Octabenzocircumbiphenyl Sorts Semiconducting Single-Walled Carbon Nanotubes with Structural Specificity. United States. https://doi.org/10.1021/acs.chemmater.6b04018
Gao, Jia, Sengar, Nikita, Wu, Ying, Jockusch, Steffen, Nuckolls, Colin, Clancy, Paulette, and Loo, Yueh-Lin. Sun . "Contorted Octabenzocircumbiphenyl Sorts Semiconducting Single-Walled Carbon Nanotubes with Structural Specificity". United States. https://doi.org/10.1021/acs.chemmater.6b04018. https://www.osti.gov/servlets/purl/1534447.
@article{osti_1534447,
title = {Contorted Octabenzocircumbiphenyl Sorts Semiconducting Single-Walled Carbon Nanotubes with Structural Specificity},
author = {Gao, Jia and Sengar, Nikita and Wu, Ying and Jockusch, Steffen and Nuckolls, Colin and Clancy, Paulette and Loo, Yueh-Lin},
abstractNote = {Here, we use a nonplanar aromatic molecule, contorted octabenzocircumbiphenyl (c-OBCB), to sort semiconducting single-walled carbon nanotubes (SWNTs) by their chiral angles. From absorption spectroscopy, photoluminescence excitation spectroscopy, and Raman spectroscopy studies, we find that c-OBCB preferentially binds and sorts for a number of semiconducting carbon nanotubes with chiral angles greater than 12°. Molecular dynamics simulations reveal that the contorted aromatic core of c-OBCB binds strongly to only certain SWNTs, especially those with matching curvature, and that this discriminatory binding interaction is reinforced by preferences of the side chains on the c-OBCB to stick to SWNT surface rather than interact with the solvent. This opens the door to side chain/solvent engineering to bias the selection of certain (m,n) SWNT variants. We also investigate the temperature dependence of hole mobility in field-effect transistors comprising c-OBCB-sorted semiconducting carbon-nanotube networks and find hole transport in these networks to be thermally activated.},
doi = {10.1021/acs.chemmater.6b04018},
journal = {Chemistry of Materials},
number = 2,
volume = 29,
place = {United States},
year = {2017},
month = {1}
}

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Figures / Tables:

Figure 1 Figure 1: (a) The graphene sheet map of SWNTs that are sorted by c-OBCB in toluene. (b) Chemical structure of cOBCB. (c) Absorption spectra of Hipco SWNTs sorted with c-OBCB (red) and with SDS (black). (d) 2D photoluminescence excitation (PLE) contour plot of c-OBCB/Hipco SWNTs dispersion identifying strong selectivity formore » (10,3) and some selectivity for (7,6), (8,7), (10,5) and (6,5) SWNTs. (e) Radial breathing mode (RBM) regions of Raman spectra of Hipco SWNTs sorted with c-OBCB (red) and with SDS (black), excited at 633 nm. The red and blue shaded areas correspond to the metallic and semiconducting SWNTs regions, respectively. (f) Absorption spectra of Comocat SWNTs sorted with c-OBCB (red) and with SDS (black).« less

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