A highly substituted pyrazinophane generated from a quinoidal system via a cascade reaction

Anderson, Christopher L.; Liang, Jiatao; Teat, Simon J.; Garzón-Ruiz, Andrés; Nenon, David P.; Navarro, Amparo; Liu, Yi

doi:10.1039/d0cc00916d

Title: A highly substituted pyrazinophane generated from a quinoidal system via a cascade reaction

Abstract

[2.2](2,5)pyrazinophanes are strained macrocycles exhibiting through-space electron density that are difficult to access synthetically. A highly-substituted member of this family is synthesized and characterized.

Authors:

^[1];

^[2];

^[3];

^[4];

^[5];

^[6]

Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Molecular Foundry; Univ. of California, Berkeley, CA (United States). Dept. of Chemistry
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Advanced Light Source (ALS)
Univ. de Castilla-La Mancha, Albacete (Spain). Dept. of Physical Chemistry
Univ. of California, Berkeley, CA (United States). Dept. of Chemistry; Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Materials Sciences Division
Univ. de Jaén, Paraje las Lagunillas (Spain). Dept. of Physical and Analytical Chemistry
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Molecular Foundry

Publication Date:: 2020-03-10

Research Org.:: Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Scientific User Facilities Division

OSTI Identifier:: 1661599

Alternate Identifier(s):: OSTI ID: 1606054

Grant/Contract Number:: AC02-05CH11231

Resource Type:: Accepted Manuscript

Journal Name:: ChemComm

Additional Journal Information:: Journal Volume: 56; Journal Issue: 32; Journal ID: ISSN 1359-7345

Publisher:: Royal Society of Chemistry

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats


                    Anderson, Christopher L., Liang, Jiatao, Teat, Simon J., Garzón-Ruiz, Andrés, Nenon, David P., Navarro, Amparo, and Liu, Yi. A highly substituted pyrazinophane generated from a quinoidal system via a cascade reaction.  United States: N. p., 2020. 
Web.  doi:10.1039/d0cc00916d.

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                    Anderson, Christopher L., Liang, Jiatao, Teat, Simon J., Garzón-Ruiz, Andrés, Nenon, David P., Navarro, Amparo, & Liu, Yi. A highly substituted pyrazinophane generated from a quinoidal system via a cascade reaction.  United States.  https://doi.org/10.1039/d0cc00916d

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                    Anderson, Christopher L., Liang, Jiatao, Teat, Simon J., Garzón-Ruiz, Andrés, Nenon, David P., Navarro, Amparo, and Liu, Yi. Tue .  
"A highly substituted pyrazinophane generated from a quinoidal system via a cascade reaction".  United States.  https://doi.org/10.1039/d0cc00916d.  https://www.osti.gov/servlets/purl/1661599.

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@article{osti_1661599,

  title        = {A highly substituted pyrazinophane generated from a quinoidal system via a cascade reaction},

  author       = {Anderson, Christopher L. and Liang, Jiatao and Teat, Simon J. and Garzón-Ruiz, Andrés and Nenon, David P. and Navarro, Amparo and Liu, Yi},

  abstractNote = {[2.2](2,5)pyrazinophanes are strained macrocycles exhibiting through-space electron density that are difficult to access synthetically. A highly-substituted member of this family is synthesized and characterized.},

  doi          = {10.1039/d0cc00916d},

  journal      = {ChemComm},

  number       = 32,

  volume       = 56,

  place        = {United States},

  year         = {2020},

  month        = {3}

}

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Works referenced in this record:

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dataset (2)

Title: A highly substituted pyrazinophane generated from a quinoidal system via a cascade reaction

Abstract

Citation Formats

Radical ions of [2.2](2,5)pyrazinophanes: an electron paramagnetic resonance study journal, January 1992

[2.2](2,6)- and [2.2](2,5)Pyrazinophanes: Synthesis and Molecular Structure journal, March 1990

[2.2](2,5)Pyrazinophanes: Synthesis and Molecular Structure journal, January 1988

Electronic Tuning of Mixed Quinoidal‐Aromatic Conjugated Polyelectrolytes: Direct Ionic Substitution on Polymer Main‐Chains journal, December 2019

Macro Rings. XX. Transannular Effects in π-π-Complexes 1 journal, November 1959

para -Azaquinodimethane: A Compact Quinodimethane Variant as an Ambient Stable Building Block for High-Performance Low Band Gap Polymers journal, June 2017

The Chemistry of Xylylenes. III. Some Reactions of p-Xylylene that Occur by Free Radical Intermediates 2 journal, January 1960

Polymerizations of nitrogen-containing heterophanes by vapor deposition method, transformation to polymeric films bearing a conjugated structure, and their properties journal, September 1995

Poly( p -xylylene) and Its Derivatives by Chemical Vapor Deposition: Synthesis, Mechanism, and Structure journal, December 1998

Bichromophoric Paracyclophanes: Models for Interchromophore Delocalization journal, January 2001

Neihumicin, a new cytotoxic antibiotic from Micromonospora neihuensis. II. Structural determination and total synthesis. journal, January 1988

Cyclophane chemistry: bent and battered benzene rings journal, June 1971

Exclusive Formation of Bridge-Substituted [2.2]Paracyclophane by Topochemical Photocycloaddition Reaction of Unsymmetrical Substituted p -Quinodimethane journal, May 2017

Vapor Deposition Polymerization of para-Xylylene Derivatives-Mechanism and Applications journal, January 2007

Some remarks on the CH2[graphic omitted]CH2 molecule journal, January 1947

Condensation of 1,4-diacetylpiperazine-2,5-dione with aldehydes journal, January 1974

Overcoming lability of extremely long alkane carbon–carbon bonds through dispersion forces journal, September 2011

Discovery of a Class of Diketopiperazines as Antiprion Compounds journal, June 2010

Fingerprints of Through-Bond and Through-Space Exciton and Charge π-Electron Delocalization in Linearly Extended [2.2]Paracyclophanes journal, February 2017

Stilbenoid Dimers: Dissection of a Paracyclophane Chromophore journal, September 1998

Blending Through-Space and Through-Bond π–π-Coupling in [2,2′]-Paracyclophane-oligophenylenevinylene Molecular Wires journal, May 2013

[2.2]Paracyclophanes in Polymer Chemistry and Materials Science journal, December 2008

Macro rings. XXXVI. Ring expansion, racemization, and isomer interconversions in the [2.2]paracyclophane system through a diradical intermediate journal, June 1969

Electronic Tuning of Mixed Quinoidal‐Aromatic Conjugated Polyelectrolytes: Direct Ionic Substitution on Polymer Main‐Chains journal, October 2019

Radical ions of [2.2](2,5)pyrazinophanes: an electron paramagnetic resonance study
journal, January 1992

[2.2](2,6)- and [2.2](2,5)Pyrazinophanes: Synthesis and Molecular Structure
journal, March 1990

[2.2](2,5)Pyrazinophanes: Synthesis and Molecular Structure
journal, January 1988

Electronic Tuning of Mixed Quinoidal‐Aromatic Conjugated Polyelectrolytes: Direct Ionic Substitution on Polymer Main‐Chains
journal, December 2019

Macro Rings. XX. Transannular Effects in π-π-Complexes ¹
journal, November 1959

para -Azaquinodimethane: A Compact Quinodimethane Variant as an Ambient Stable Building Block for High-Performance Low Band Gap Polymers
journal, June 2017

The Chemistry of Xylylenes. III. Some Reactions of p-Xylylene that Occur by Free Radical Intermediates ²
journal, January 1960

Polymerizations of nitrogen-containing heterophanes by vapor deposition method, transformation to polymeric films bearing a conjugated structure, and their properties
journal, September 1995

Poly( p -xylylene) and Its Derivatives by Chemical Vapor Deposition: Synthesis, Mechanism, and Structure
journal, December 1998

Bichromophoric Paracyclophanes: Models for Interchromophore Delocalization
journal, January 2001

Neihumicin, a new cytotoxic antibiotic from Micromonospora neihuensis. II. Structural determination and total synthesis.
journal, January 1988

Cyclophane chemistry: bent and battered benzene rings
journal, June 1971

Exclusive Formation of Bridge-Substituted [2.2]Paracyclophane by Topochemical Photocycloaddition Reaction of Unsymmetrical Substituted p -Quinodimethane
journal, May 2017

Vapor Deposition Polymerization of para-Xylylene Derivatives-Mechanism and Applications
journal, January 2007

Some remarks on the CH2[graphic omitted]CH2 molecule
journal, January 1947

Condensation of 1,4-diacetylpiperazine-2,5-dione with aldehydes
journal, January 1974

Overcoming lability of extremely long alkane carbon–carbon bonds through dispersion forces
journal, September 2011

Discovery of a Class of Diketopiperazines as Antiprion Compounds
journal, June 2010

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journal, February 2017

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journal, September 1998

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journal, May 2013

[2.2]Paracyclophanes in Polymer Chemistry and Materials Science
journal, December 2008

Macro rings. XXXVI. Ring expansion, racemization, and isomer interconversions in the [2.2]paracyclophane system through a diradical intermediate
journal, June 1969

Electronic Tuning of Mixed Quinoidal‐Aromatic Conjugated Polyelectrolytes: Direct Ionic Substitution on Polymer Main‐Chains
journal, October 2019