Inserting Porphyrin Quantum Dots in Bottom-Up Synthesized Graphene Nanoribbons

doi:10.1002/chem.201705252

Title: 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:

Perkins, Wade ^[1];

^[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:: 2017-11-06

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.

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                    Perkins, Wade, & Fischer, Felix R. Inserting Porphyrin Quantum Dots in Bottom-Up Synthesized Graphene Nanoribbons.  United States.  doi:10.1002/chem.201705252.

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                    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.

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@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}

}

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DOI: 10.1002/chem.201705252

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Title: Inserting Porphyrin Quantum Dots in Bottom-Up Synthesized Graphene Nanoribbons

Abstract

Citation Formats

Energy Gaps in Graphene Nanoribbons journal, November 2006

Graphene nanoribbon blends with P3HT for organic electronics journal, January 2014

Graphene spintronics journal, October 2014

Mechanistic study of the synthesis and spectral properties of meso-tetraarylporphyrins journal, May 1972

Optical properties of graphene nanoribbons: The role of many-body effects journal, January 2008

On-surface synthesis of graphene nanoribbons with zigzag edge topology journal, March 2016

Synthesis of structurally well-defined and liquid-phase-processable graphene nanoribbons journal, December 2013

Quantum dot states and optical excitations of edge-modulated graphene nanoribbons journal, July 2011

Two-Dimensional Graphene Nanoribbons journal, April 2008

Tunneling Spin Injection into Single Layer Graphene journal, October 2010

Bottom-Up Synthesis of N = 13 Sulfur-Doped Graphene Nanoribbons journal, January 2016

Tuning the Band Gap of Graphene Nanoribbons Synthesized from Molecular Precursors journal, June 2013

Bottom-Up Synthesis of Liquid-Phase-Processable Graphene Nanoribbons with Near-Infrared Absorption journal, October 2014

On-Surface Synthesis of Rylene-Type Graphene Nanoribbons journal, March 2015

Electronic Structure and Stability of Semiconducting Graphene Nanoribbons journal, December 2006

Large-scale solution synthesis of narrow graphene nanoribbons journal, February 2014

Superbenzol-Porphyrin-Konjugate journal, September 2014

Atomically precise bottom-up fabrication of graphene nanoribbons journal, July 2010

Quantum Dots Embedded in Graphene Nanoribbons by Chemical Substitution journal, December 2016

Graphene nanoribbon heterojunctions journal, September 2014

Quasiparticle Energies and Band Gaps in Graphene Nanoribbons journal, November 2007

Atomically controlled substitutional boron-doping of graphene nanoribbons journal, August 2015

First-principles study of edge states of H-terminated graphitic ribbons journal, April 1999

Three Short Stories about Hexaarylbenzene-Porphyrin Scaffolds journal, October 2016

Soluble Graphene Nanoribbons from Planarization of Oligophenylenes journal, December 2016

Superbenzene-Porphyrin Conjugates journal, September 2014

Edge state in graphene ribbons: Nanometer size effect and edge shape dependence journal, December 1996

Molecular bandgap engineering of bottom-up synthesized graphene nanoribbon heterojunctions journal, January 2015

Ambipolar Transport in Solution-Synthesized Graphene Nanoribbons journal, April 2016

Direct visualization of atomically precise nitrogen-doped graphene nanoribbons journal, July 2014

HBC–porphyrin – close contact chromophores journal, January 2013

Room-temperature magnetic order on zigzag edges of narrow graphene nanoribbons journal, October 2014

Electronic Structure of Atomically Precise Graphene Nanoribbons journal, July 2012

Electronic transport properties of nanographite ribbon junctions journal, September 2001

On-Surface Synthesis and Characterization of 9-Atom Wide Armchair Graphene Nanoribbons journal, February 2017

Half-metallic graphene nanoribbons journal, November 2006

Graphene-enabled low-control quantum gates between static and mobile spins journal, February 2014

Site-Specific Substitutional Boron Doping of Semiconducting Armchair Graphene Nanoribbons journal, July 2015

Heterostructures through Divergent Edge Reconstruction in Nitrogen-Doped Segmented Graphene Nanoribbons journal, August 2016

Electronic Communication across Porphyrin Hexabenzocoronene Isomers journal, May 2019

Synthesis of Triply Fused Porphyrin-Nanographene Conjugates journal, August 2018

Synthesis of Triply Fused Porphyrin-Nanographene Conjugates journal, August 2018

Electronic Communication across Porphyrin Hexabenzocoronene Isomers journal, May 2019

Synthesis of Triply Fused Porphyrin-Nanographene Conjugates journal, August 2018

Exploration of Interfacial Porphine Coupling Schemes and Hybrid Systems by Bond‐Resolved Scanning Probe Microscopy journal, October 2018

Elektronische Kommunikation von Porphyrin‐Hexabenzocoronen‐Isomeren journal, May 2019

On‐Surface Synthesis and Characterization of Triply Fused Porphyrin–Graphene Nanoribbon Hybrids journal, December 2019

Exploration of Interfacial Porphine Coupling Schemes and Hybrid Systems by Bond‐Resolved Scanning Probe Microscopy journal, December 2018

On‐Surface Synthesis and Characterization of Triply Fused Porphyrin–Graphene Nanoribbon Hybrids journal, December 2019

Energy Gaps in Graphene Nanoribbons
journal, November 2006

Graphene nanoribbon blends with P3HT for organic electronics
journal, January 2014

Graphene spintronics
journal, October 2014

Mechanistic study of the synthesis and spectral properties of meso-tetraarylporphyrins
journal, May 1972

Optical properties of graphene nanoribbons: The role of many-body effects
journal, January 2008

On-surface synthesis of graphene nanoribbons with zigzag edge topology
journal, March 2016

Synthesis of structurally well-defined and liquid-phase-processable graphene nanoribbons
journal, December 2013

Quantum dot states and optical excitations of edge-modulated graphene nanoribbons
journal, July 2011

Two-Dimensional Graphene Nanoribbons
journal, April 2008

Tunneling Spin Injection into Single Layer Graphene
journal, October 2010

Bottom-Up Synthesis of N = 13 Sulfur-Doped Graphene Nanoribbons
journal, January 2016

Tuning the Band Gap of Graphene Nanoribbons Synthesized from Molecular Precursors
journal, June 2013

Bottom-Up Synthesis of Liquid-Phase-Processable Graphene Nanoribbons with Near-Infrared Absorption
journal, October 2014

On-Surface Synthesis of Rylene-Type Graphene Nanoribbons
journal, March 2015

Electronic Structure and Stability of Semiconducting Graphene Nanoribbons
journal, December 2006

Large-scale solution synthesis of narrow graphene nanoribbons
journal, February 2014

Superbenzol-Porphyrin-Konjugate
journal, September 2014

Atomically precise bottom-up fabrication of graphene nanoribbons
journal, July 2010

Quantum Dots Embedded in Graphene Nanoribbons by Chemical Substitution
journal, December 2016

Graphene nanoribbon heterojunctions
journal, September 2014

Quasiparticle Energies and Band Gaps in Graphene Nanoribbons
journal, November 2007

Atomically controlled substitutional boron-doping of graphene nanoribbons
journal, August 2015

First-principles study of edge states of H-terminated graphitic ribbons
journal, April 1999

Three Short Stories about Hexaarylbenzene-Porphyrin Scaffolds
journal, October 2016

Soluble Graphene Nanoribbons from Planarization of Oligophenylenes
journal, December 2016

Superbenzene-Porphyrin Conjugates
journal, September 2014

Edge state in graphene ribbons: Nanometer size effect and edge shape dependence
journal, December 1996

Molecular bandgap engineering of bottom-up synthesized graphene nanoribbon heterojunctions
journal, January 2015

Ambipolar Transport in Solution-Synthesized Graphene Nanoribbons
journal, April 2016

Direct visualization of atomically precise nitrogen-doped graphene nanoribbons
journal, July 2014

HBC–porphyrin – close contact chromophores
journal, January 2013

Room-temperature magnetic order on zigzag edges of narrow graphene nanoribbons
journal, October 2014

Electronic Structure of Atomically Precise Graphene Nanoribbons
journal, July 2012

Electronic transport properties of nanographite ribbon junctions
journal, September 2001

On-Surface Synthesis and Characterization of 9-Atom Wide Armchair Graphene Nanoribbons
journal, February 2017

Half-metallic graphene nanoribbons
journal, November 2006

Graphene-enabled low-control quantum gates between static and mobile spins
journal, February 2014

Site-Specific Substitutional Boron Doping of Semiconducting Armchair Graphene Nanoribbons
journal, July 2015

Heterostructures through Divergent Edge Reconstruction in Nitrogen-Doped Segmented Graphene Nanoribbons
journal, August 2016

Electronic Communication across Porphyrin Hexabenzocoronene Isomers
journal, May 2019

Synthesis of Triply Fused Porphyrin-Nanographene Conjugates
journal, August 2018

Synthesis of Triply Fused Porphyrin-Nanographene Conjugates
journal, August 2018

Electronic Communication across Porphyrin Hexabenzocoronene Isomers
journal, May 2019

Synthesis of Triply Fused Porphyrin-Nanographene Conjugates
journal, August 2018

Exploration of Interfacial Porphine Coupling Schemes and Hybrid Systems by Bond‐Resolved Scanning Probe Microscopy
journal, October 2018

Elektronische Kommunikation von Porphyrin‐Hexabenzocoronen‐Isomeren
journal, May 2019

On‐Surface Synthesis and Characterization of Triply Fused Porphyrin–Graphene Nanoribbon Hybrids
journal, December 2019

Exploration of Interfacial Porphine Coupling Schemes and Hybrid Systems by Bond‐Resolved Scanning Probe Microscopy
journal, December 2018

On‐Surface Synthesis and Characterization of Triply Fused Porphyrin–Graphene Nanoribbon Hybrids
journal, December 2019