Inserting Porphyrin Quantum Dots in Bottom-Up Synthesized Graphene Nanoribbons
Abstract
Diels–Alder copolymerization of tetraphenylcyclopentadienone, a precursor for cove graphene nanoribbons (cGNRs), with bifunctional porphyrins yields defined nanostructures comprised of a single cGNR-porphyrin-cGNR heterojunction within each ribbon. 13C NMR labeling and high-resolution mass spectrometry of solubilized polymer intermediates indicates that every porphyrin is covalently linked to two extended segments of cGNRs. UV/Vis absorption and fluorescence emission spectroscopy reveal a strong electronic correlation between the porphyrin and the adjacent cGNR segments that can be attenuated through reversible metalation of the porphyrin core. This versatile bottom-up synthetic strategy provides access to structurally well-defined, functional GNR-quantum dot-GNR heterostructures within a single graphene nanoribbon.
- Authors:
-
[2]
- Univ. of California, Berkeley, CA (United States). Dept. of Chemistry
- Univ. of California, Berkeley, CA (United States). Dept. of Chemistry; Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Materials Science Division; Univ. of California, Berkeley, CA (United States). Kavli Energy NanoSciences Inst.
- Publication Date:
- Research Org.:
- Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Materials Sciences & Engineering Division; USDOE
- OSTI Identifier:
- 1461124
- Alternate Identifier(s):
- OSTI ID: 1410700
- Grant/Contract Number:
- AC02-05CH11231; SC0010409
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Chemistry - A European Journal
- Additional Journal Information:
- Journal Volume: 23; Journal Issue: 70; Journal ID: ISSN 0947-6539
- Publisher:
- ChemPubSoc Europe
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 36 MATERIALS SCIENCE
Citation Formats
Perkins, Wade, and Fischer, Felix R. Inserting Porphyrin Quantum Dots in Bottom-Up Synthesized Graphene Nanoribbons. United States: N. p., 2017.
Web. doi:10.1002/chem.201705252.
Perkins, Wade, & Fischer, Felix R. Inserting Porphyrin Quantum Dots in Bottom-Up Synthesized Graphene Nanoribbons. United States. doi:10.1002/chem.201705252.
Perkins, Wade, and Fischer, Felix R. Mon .
"Inserting Porphyrin Quantum Dots in Bottom-Up Synthesized Graphene Nanoribbons". United States. doi:10.1002/chem.201705252. https://www.osti.gov/servlets/purl/1461124.
@article{osti_1461124,
title = {Inserting Porphyrin Quantum Dots in Bottom-Up Synthesized Graphene Nanoribbons},
author = {Perkins, Wade and Fischer, Felix R.},
abstractNote = {Diels–Alder copolymerization of tetraphenylcyclopentadienone, a precursor for cove graphene nanoribbons (cGNRs), with bifunctional porphyrins yields defined nanostructures comprised of a single cGNR-porphyrin-cGNR heterojunction within each ribbon.13C NMR labeling and high-resolution mass spectrometry of solubilized polymer intermediates indicates that every porphyrin is covalently linked to two extended segments of cGNRs. UV/Vis absorption and fluorescence emission spectroscopy reveal a strong electronic correlation between the porphyrin and the adjacent cGNR segments that can be attenuated through reversible metalation of the porphyrin core. This versatile bottom-up synthetic strategy provides access to structurally well-defined, functional GNR-quantum dot-GNR heterostructures within a single graphene nanoribbon.},
doi = {10.1002/chem.201705252},
journal = {Chemistry - A European Journal},
number = 70,
volume = 23,
place = {United States},
year = {2017},
month = {11}
}
Free Publicly Available Full Text
Publisher's Version of Record
Other availability
Search WorldCat to find libraries that may hold this journal
Cited by: 3 works
Citation information provided by
Web of Science
Web of Science
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.
Works referenced in this record:
Energy Gaps in Graphene Nanoribbons
journal, November 2006
- Son, Young-Woo; Cohen, Marvin L.; Louie, Steven G.
- Physical Review Letters, Vol. 97, Issue 21
Graphene nanoribbon blends with P3HT for organic electronics
journal, January 2014
- El Gemayel, Mirella; Narita, Akimitsu; Dössel, Lukas F.
- Nanoscale, Vol. 6, Issue 12
Graphene spintronics
journal, October 2014
- Han, Wei; Kawakami, Roland K.; Gmitra, Martin
- Nature Nanotechnology, Vol. 9, Issue 10
Mechanistic study of the synthesis and spectral properties of meso-tetraarylporphyrins
journal, May 1972
- Kim, Jean B.; Leonard, John J.; Longo, Frederick R.
- Journal of the American Chemical Society, Vol. 94, Issue 11
Optical properties of graphene nanoribbons: The role of many-body effects
journal, January 2008
- Prezzi, Deborah; Varsano, Daniele; Ruini, Alice
- Physical Review B, Vol. 77, Issue 4
On-surface synthesis of graphene nanoribbons with zigzag edge topology
journal, March 2016
- Ruffieux, Pascal; Wang, Shiyong; Yang, Bo
- Nature, Vol. 531, Issue 7595
Synthesis of structurally well-defined and liquid-phase-processable graphene nanoribbons
journal, December 2013
- Narita, Akimitsu; Feng, Xinliang; Hernandez, Yenny
- Nature Chemistry, Vol. 6, Issue 2
Quantum dot states and optical excitations of edge-modulated graphene nanoribbons
journal, July 2011
- Prezzi, Deborah; Varsano, Daniele; Ruini, Alice
- Physical Review B, Vol. 84, Issue 4
Two-Dimensional Graphene Nanoribbons
journal, April 2008
- Yang, Xiaoyin; Dou, Xi; Rouhanipour, Ali
- Journal of the American Chemical Society, Vol. 130, Issue 13
Tunneling Spin Injection into Single Layer Graphene
journal, October 2010
- Han, Wei; Pi, K.; McCreary, K. M.
- Physical Review Letters, Vol. 105, Issue 16
Bottom-Up Synthesis of N = 13 Sulfur-Doped Graphene Nanoribbons
journal, January 2016
- Nguyen, Giang D.; Toma, Francesca M.; Cao, Ting
- The Journal of Physical Chemistry C, Vol. 120, Issue 5
Tuning the Band Gap of Graphene Nanoribbons Synthesized from Molecular Precursors
journal, June 2013
- Chen, Yen-Chia; de Oteyza, Dimas G.; Pedramrazi, Zahra
- ACS Nano, Vol. 7, Issue 7
Bottom-Up Synthesis of Liquid-Phase-Processable Graphene Nanoribbons with Near-Infrared Absorption
journal, October 2014
- Narita, Akimitsu; Verzhbitskiy, Ivan A.; Frederickx, Wout
- ACS Nano, Vol. 8, Issue 11
On-Surface Synthesis of Rylene-Type Graphene Nanoribbons
journal, March 2015
- Zhang, Haiming; Lin, Haiping; Sun, Kewei
- Journal of the American Chemical Society, Vol. 137, Issue 12
Electronic Structure and Stability of Semiconducting Graphene Nanoribbons
journal, December 2006
- Barone, Verónica; Hod, Oded; Scuseria, Gustavo E.
- Nano Letters, Vol. 6, Issue 12
Large-scale solution synthesis of narrow graphene nanoribbons
journal, February 2014
- Vo, Timothy H.; Shekhirev, Mikhail; Kunkel, Donna A.
- Nature Communications, Vol. 5, Issue 1
Superbenzol-Porphyrin-Konjugate
journal, September 2014
- Lungerich, Dominik; Hitzenberger, Jakob F.; Marcia, Mario
- Angewandte Chemie, Vol. 126, Issue 45
Atomically precise bottom-up fabrication of graphene nanoribbons
journal, July 2010
- Cai, Jinming; Ruffieux, Pascal; Jaafar, Rached
- Nature, Vol. 466, Issue 7305
Quantum Dots Embedded in Graphene Nanoribbons by Chemical Substitution
journal, December 2016
- Carbonell-Sanromà, Eduard; Brandimarte, Pedro; Balog, Richard
- Nano Letters, Vol. 17, Issue 1
Graphene nanoribbon heterojunctions
journal, September 2014
- Cai, Jinming; Pignedoli, Carlo A.; Talirz, Leopold
- Nature Nanotechnology, Vol. 9, Issue 11
Quasiparticle Energies and Band Gaps in Graphene Nanoribbons
journal, November 2007
- Yang, Li; Park, Cheol-Hwan; Son, Young-Woo
- Physical Review Letters, Vol. 99, Issue 18
Atomically controlled substitutional boron-doping of graphene nanoribbons
journal, August 2015
- Kawai, Shigeki; Saito, Shohei; Osumi, Shinichiro
- Nature Communications, Vol. 6, Issue 1
First-principles study of edge states of H-terminated graphitic ribbons
journal, April 1999
- Miyamoto, Yoshiyuki; Nakada, Kyoko; Fujita, Mitsutaka
- Physical Review B, Vol. 59, Issue 15
Three Short Stories about Hexaarylbenzene-Porphyrin Scaffolds
journal, October 2016
- Lungerich, Dominik; Hitzenberger, Jakob F.; Donaubauer, Wolfgang
- Chemistry - A European Journal, Vol. 22, Issue 47
Soluble Graphene Nanoribbons from Planarization of Oligophenylenes
journal, December 2016
- Sen, Choong Ping; Valiyaveettil, Suresh
- Chemistry - A European Journal, Vol. 23, Issue 7
Superbenzene-Porphyrin Conjugates
journal, September 2014
- Lungerich, Dominik; Hitzenberger, Jakob F.; Marcia, Mario
- Angewandte Chemie International Edition, Vol. 53, Issue 45
Edge state in graphene ribbons: Nanometer size effect and edge shape dependence
journal, December 1996
- Nakada, Kyoko; Fujita, Mitsutaka; Dresselhaus, Gene
- Physical Review B, Vol. 54, Issue 24
Molecular bandgap engineering of bottom-up synthesized graphene nanoribbon heterojunctions
journal, January 2015
- Chen, Yen-Chia; Cao, Ting; Chen, Chen
- Nature Nanotechnology, Vol. 10, Issue 2
Ambipolar Transport in Solution-Synthesized Graphene Nanoribbons
journal, April 2016
- Gao, Jia; Uribe-Romo, Fernando J.; Saathoff, Jonathan D.
- ACS Nano, Vol. 10, Issue 4
Direct visualization of atomically precise nitrogen-doped graphene nanoribbons
journal, July 2014
- Zhang, Yi; Zhang, Yanfang; Li, Geng
- Applied Physics Letters, Vol. 105, Issue 2
HBC–porphyrin – close contact chromophores
journal, January 2013
- Englert, Jan M.; Malig, Jenny; Zamolo, Valeria Anna
- Chemical Communications, Vol. 49, Issue 42
Room-temperature magnetic order on zigzag edges of narrow graphene nanoribbons
journal, October 2014
- Magda, Gábor Zsolt; Jin, Xiaozhan; Hagymási, Imre
- Nature, Vol. 514, Issue 7524
Electronic Structure of Atomically Precise Graphene Nanoribbons
journal, July 2012
- Ruffieux, Pascal; Cai, Jinming; Plumb, Nicholas C.
- ACS Nano, Vol. 6, Issue 8
Electronic transport properties of nanographite ribbon junctions
journal, September 2001
- Wakabayashi, Katsunori
- Physical Review B, Vol. 64, Issue 12
On-Surface Synthesis and Characterization of 9-Atom Wide Armchair Graphene Nanoribbons
journal, February 2017
- Talirz, Leopold; Söde, Hajo; Dumslaff, Tim
- ACS Nano, Vol. 11, Issue 2
Half-metallic graphene nanoribbons
journal, November 2006
- Son, Young-Woo; Cohen, Marvin L.; Louie, Steven G.
- Nature, Vol. 444, Issue 7117
Graphene-enabled low-control quantum gates between static and mobile spins
journal, February 2014
- Cordourier-Maruri, G.; Omar, Y.; de Coss, R.
- Physical Review B, Vol. 89, Issue 7
Site-Specific Substitutional Boron Doping of Semiconducting Armchair Graphene Nanoribbons
journal, July 2015
- Cloke, Ryan R.; Marangoni, Tomas; Nguyen, Giang D.
- Journal of the American Chemical Society, Vol. 137, Issue 28
Heterostructures through Divergent Edge Reconstruction in Nitrogen-Doped Segmented Graphene Nanoribbons
journal, August 2016
- Marangoni, Tomas; Haberer, Danny; Rizzo, Daniel J.
- Chemistry - A European Journal, Vol. 22, Issue 37
Works referencing / citing this record:
Synthesis of Triply Fused Porphyrin-Nanographene Conjugates
journal, August 2018
- Chen, Qiang; Brambilla, Luigi; Daukiya, Lakshya
- Angewandte Chemie International Edition, Vol. 57, Issue 35
Electronic Communication across Porphyrin Hexabenzocoronene Isomers
journal, May 2019
- Martin, Max M.; Lungerich, Dominik; Haines, Philipp
- Angewandte Chemie International Edition, Vol. 58, Issue 26