Zirconacyclopentadiene‐Annulated Polycyclic Aromatic Hydrocarbons

Kiel, Gavin R.; Ziegler, Micah S.; Tilley, T. Don

doi:10.1002/anie.201700818

Title: Zirconacyclopentadiene‐Annulated Polycyclic Aromatic Hydrocarbons

Abstract

Abstract Syntheses of large polycyclic aromatic hydrocarbons (PAHs) and graphene nanostructures demand methods that are capable of selectively and efficiently fusing large numbers of aromatic rings, yet such methods remain scarce. Herein, we report a new approach that is based on the quantitative intramolecular reductive cyclization of an oligo(diyne) with a low‐valent zirconocene reagent, which gives a PAH with one or more annulated zirconacyclopentadienes (ZrPAHs). The efficiency of this process is demonstrated by a high‐yielding fivefold intramolecular coupling to form a helical ZrPAH with 16 fused rings (from a precursor with no fused rings). Several other PAH topologies are also reported. Protodemetalation of the ZrPAHs allowed full characterization (including by X‐ray crystallography) of PAHs containing one or more appended dienes with the ortho‐quinodimethane (o‐QDM) structure, which are usually too reactive for isolation and are potentially valuable for the fusion of additional rings by Diels–Alder reactions.

Authors:

^[1];

^[1]; Tilley, T. Don ^[1]

Department of Chemistry University of California Berkeley CA 94720 USA

Publication Date:: Thu Mar 23 00:00:00 EDT 2017

Sponsoring Org.:: USDOE

OSTI Identifier:: 1401284

Grant/Contract Number:: AC02-05CH11231

Resource Type:: Publisher's Accepted Manuscript

Journal Name:: Angewandte Chemie (International Edition)

Additional Journal Information:: Journal Name: Angewandte Chemie (International Edition) Journal Volume: 56 Journal Issue: 17; Journal ID: ISSN 1433-7851

Publisher:: Wiley Blackwell (John Wiley & Sons)

Country of Publication:: Germany

Language:: English

Citation Formats


                    Kiel, Gavin R., Ziegler, Micah S., and Tilley, T. Don. Zirconacyclopentadiene‐Annulated Polycyclic Aromatic Hydrocarbons.  Germany: N. p., 2017. 
Web.  doi:10.1002/anie.201700818.

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                    Kiel, Gavin R., Ziegler, Micah S., & Tilley, T. Don. Zirconacyclopentadiene‐Annulated Polycyclic Aromatic Hydrocarbons.  Germany.  https://doi.org/10.1002/anie.201700818

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                    Kiel, Gavin R., Ziegler, Micah S., and Tilley, T. Don. Thu .  
"Zirconacyclopentadiene‐Annulated Polycyclic Aromatic Hydrocarbons".  Germany.  https://doi.org/10.1002/anie.201700818.

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@article{osti_1401284,

  title        = {Zirconacyclopentadiene‐Annulated Polycyclic Aromatic Hydrocarbons},

  author       = {Kiel, Gavin R. and Ziegler, Micah S. and Tilley, T. Don},

  abstractNote = {Abstract Syntheses of large polycyclic aromatic hydrocarbons (PAHs) and graphene nanostructures demand methods that are capable of selectively and efficiently fusing large numbers of aromatic rings, yet such methods remain scarce. Herein, we report a new approach that is based on the quantitative intramolecular reductive cyclization of an oligo(diyne) with a low‐valent zirconocene reagent, which gives a PAH with one or more annulated zirconacyclopentadienes (ZrPAHs). The efficiency of this process is demonstrated by a high‐yielding fivefold intramolecular coupling to form a helical ZrPAH with 16 fused rings (from a precursor with no fused rings). Several other PAH topologies are also reported. Protodemetalation of the ZrPAHs allowed full characterization (including by X‐ray crystallography) of PAHs containing one or more appended dienes with the ortho‐quinodimethane (o‐QDM) structure, which are usually too reactive for isolation and are potentially valuable for the fusion of additional rings by Diels–Alder reactions.},

  doi          = {10.1002/anie.201700818},

  journal      = {Angewandte Chemie (International Edition)},

  number       = 17,

  volume       = 56,

  place        = {Germany},

  year         = {Thu Mar 23 00:00:00 EDT 2017},

  month        = {Thu Mar 23 00:00:00 EDT 2017}

}

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Title: Zirconacyclopentadiene‐Annulated Polycyclic Aromatic Hydrocarbons

Abstract

Citation Formats

Carbon‐Rich Compounds book, February 2006

Discotic liquid crystals: a new generation of organic semiconductors journal, January 2007

The Diyne Reaction of 1,4-, 1,5-, 1,6-, and 1,7-Diynes via Transition Metal Complexes to New Compounds* journal, January 1974

Contorted Polycyclic Aromatics journal, December 2014

New advances in nanographene chemistry journal, January 2015

Heteroarenes as high performance organic semiconductors journal, January 2013

Making Benzotrithiophene a Stronger Electron Donor journal, November 2011

Structurally uniform and atomically precise carbon nanostructures journal, January 2016

Total Syntheses and Structures of Angular [6]- and [7]Phenylene: The First Helical Phenylenes (Heliphenes) journal, September 2002

Low band gap polycyclic hydrocarbons: from closed-shell near infrared dyes and semiconductors to open-shell radicals journal, January 2012

o -Quinodimethanes: Efficient Intermediates in Organic Synthesis journal, November 1999

Assembly of Macrocycles by Zirconocene-Mediated, Reversible Carbon−Carbon Bond Formation journal, June 2011

Synthesis of [5]-, [6]-, and [7]Helicene via Ni(0)- or Co(I)-Catalyzed Isomerization of Aromatic cis , cis -Dienetriynes journal, August 2002

A Zirconocene-Coupling Route to Substituted Poly( p -phenylenedienylene)s: Band Gap Tuning via Conformational Control journal, May 1998

Struktur, Eigenschaften und NMR-spektroskopische Charakterisierung von Cp2Zr(Pyridin)(Me3SiC?CSiMe3) journal, January 1995

Synthesis of Fluoranthenes and Indenocorannulenes: Elucidation of Chiral Stereoisomers on the Basis of Static Molecular Bowls journal, May 2006

7,7,8,8-Tetraaryl- o -quinodimethane Stabilized by Dibenzo Annulation: A Helical π-Electron System That Exhibits Electrochromic and Unique Chiroptical Properties journal, November 2012

Synthesis of 9,10-cyclobutenophenanthrene from 9,10-dimethylene-9,10-dihydrophenanthrene journal, April 1972

Graphene: Status and Prospects journal, June 2009

Total Syntheses and Structures of Angular [6]- and [7]Phenylene: The First Helical Phenylenes (Heliphenes) journal, September 2002

Forever young: polycyclic aromatic hydrocarbons as model cases for structural and optical studies journal, January 2010

Controlling the Scholl Reaction journal, March 2007

Conversion of Zirconacyclopentadienes into Metalloles: Fagan–Nugent Reaction and Beyond journal, April 2015

Synthesis and Characterization of Quarteranthene: Elucidating the Characteristics of the Edge State of Graphene Nanoribbons at the Molecular Level journal, January 2013

One-Pot Synthesis of Stable NIR Tetracene Diimides via Double Cross-Coupling journal, November 2011

A general approach to triphenylenes and azatriphenylenes: total synthesis of dehydrotylophorine and tylophorine journal, January 2008

Isolation of o-xylylene (o-quinodimethane) dirivatives. A strong through-bond interaction in 2,3-benzobicyclo[2.2.0]hexane system journal, January 1982

Cyclobutarenes and Related Compounds journal, April 2003

Polycyclic Aromatic Hydrocarbons by Ring-Closing Metathesis journal, October 2005

Graphenes as Potential Material for Electronics journal, March 2007

An Efficient, Modular Synthetic Route to Oligomers Based on Zirconocene Coupling: Properties for Phenylene–Thiophene-1-Oxide and Phenylene–Thiophene-1,1-Dioxide Chains journal, August 2000

Dibenzophosphapentaphenes: Exploiting P Chemistry for Gap Fine-Tuning and Coordination-Driven Assembly of Planar Polycyclic Aromatic Hydrocarbons journal, April 2012

Reaction of zirconocene dichloride with alkyllithiums or alkyl grignard reagents as a convenient method for generating a “zirconocene” equivalant and its use in zirconium-promoted cyclization of alkenes, alkynes, dienes, enynes, and diynes journal, January 1986

Directed Electrophilic Cyclizations: Efficient Methodology for the Synthesis of Fused Polycyclic Aromatics journal, May 1997

Metal-Catalyzed Annulation Reactions for π-Conjugated Polycycles journal, March 2014

Homologation Method for Preparation of Substituted Pentacenes and Naphthacenes journal, October 2006

New Zirconocene-Coupling Route to Large, Functionalized Macrocycles journal, October 2000

Carbon‐Rich Compounds
book, February 2006

Discotic liquid crystals: a new generation of organic semiconductors
journal, January 2007

The Diyne Reaction of 1,4-, 1,5-, 1,6-, and 1,7-Diynes via Transition Metal Complexes to New Compounds*
journal, January 1974

Contorted Polycyclic Aromatics
journal, December 2014

New advances in nanographene chemistry
journal, January 2015

Heteroarenes as high performance organic semiconductors
journal, January 2013

Making Benzotrithiophene a Stronger Electron Donor
journal, November 2011

Structurally uniform and atomically precise carbon nanostructures
journal, January 2016

Total Syntheses and Structures of Angular [6]- and [7]Phenylene: The First Helical Phenylenes (Heliphenes)
journal, September 2002

Low band gap polycyclic hydrocarbons: from closed-shell near infrared dyes and semiconductors to open-shell radicals
journal, January 2012

o -Quinodimethanes: Efficient Intermediates in Organic Synthesis
journal, November 1999

Assembly of Macrocycles by Zirconocene-Mediated, Reversible Carbon−Carbon Bond Formation
journal, June 2011

Synthesis of [5]-, [6]-, and [7]Helicene via Ni(0)- or Co(I)-Catalyzed Isomerization of Aromatic cis , cis -Dienetriynes
journal, August 2002

A Zirconocene-Coupling Route to Substituted Poly( p -phenylenedienylene)s: Band Gap Tuning via Conformational Control
journal, May 1998

Struktur, Eigenschaften und NMR-spektroskopische Charakterisierung von Cp2Zr(Pyridin)(Me3SiC?CSiMe3)
journal, January 1995

Synthesis of Fluoranthenes and Indenocorannulenes: Elucidation of Chiral Stereoisomers on the Basis of Static Molecular Bowls
journal, May 2006

7,7,8,8-Tetraaryl- o -quinodimethane Stabilized by Dibenzo Annulation: A Helical π-Electron System That Exhibits Electrochromic and Unique Chiroptical Properties
journal, November 2012

Synthesis of 9,10-cyclobutenophenanthrene from 9,10-dimethylene-9,10-dihydrophenanthrene
journal, April 1972

Graphene: Status and Prospects
journal, June 2009

Total Syntheses and Structures of Angular [6]- and [7]Phenylene: The First Helical Phenylenes (Heliphenes)
journal, September 2002

Forever young: polycyclic aromatic hydrocarbons as model cases for structural and optical studies
journal, January 2010

Controlling the Scholl Reaction
journal, March 2007

Conversion of Zirconacyclopentadienes into Metalloles: Fagan–Nugent Reaction and Beyond
journal, April 2015

Synthesis and Characterization of Quarteranthene: Elucidating the Characteristics of the Edge State of Graphene Nanoribbons at the Molecular Level
journal, January 2013

One-Pot Synthesis of Stable NIR Tetracene Diimides via Double Cross-Coupling
journal, November 2011

A general approach to triphenylenes and azatriphenylenes: total synthesis of dehydrotylophorine and tylophorine
journal, January 2008

Isolation of o-xylylene (o-quinodimethane) dirivatives. A strong through-bond interaction in 2,3-benzobicyclo[2.2.0]hexane system
journal, January 1982

Cyclobutarenes and Related Compounds
journal, April 2003

Polycyclic Aromatic Hydrocarbons by Ring-Closing Metathesis
journal, October 2005

Graphenes as Potential Material for Electronics
journal, March 2007

An Efficient, Modular Synthetic Route to Oligomers Based on Zirconocene Coupling: Properties for Phenylene–Thiophene-1-Oxide and Phenylene–Thiophene-1,1-Dioxide Chains
journal, August 2000

Dibenzophosphapentaphenes: Exploiting P Chemistry for Gap Fine-Tuning and Coordination-Driven Assembly of Planar Polycyclic Aromatic Hydrocarbons
journal, April 2012

Reaction of zirconocene dichloride with alkyllithiums or alkyl grignard reagents as a convenient method for generating a “zirconocene” equivalant and its use in zirconium-promoted cyclization of alkenes, alkynes, dienes, enynes, and diynes
journal, January 1986

Directed Electrophilic Cyclizations: Efficient Methodology for the Synthesis of Fused Polycyclic Aromatics
journal, May 1997

Metal-Catalyzed Annulation Reactions for π-Conjugated Polycycles
journal, March 2014

Homologation Method for Preparation of Substituted Pentacenes and Naphthacenes
journal, October 2006

New Zirconocene-Coupling Route to Large, Functionalized Macrocycles
journal, October 2000