Regiochemically controlled synthesis of a β-4-β' [70]fullerene bis-adduct

Cerón, Maira R.; Castro, Edison; Neti, Venkata S. Pavan K.; Dunk, Paul W.; Echegoyen, Luis A.

doi:10.1021/acs.joc.6b02301

Title: Regiochemically controlled synthesis of a β-4-β' [70]fullerene bis-adduct

Abstract

A β-4-β' C₇₀ bis-adduct regioisomer and an uncommon mono-adduct β-malonate C₇₀ derivative were synthesized by using a Diels–Alder cycloaddition followed by an addition–elimination of bromo-ethylmalonate and a retro-Diels–Alder cycloaddition reaction. Here, we also report the regioselective synthesis and spectroscopic characterization of C_s-symmetric tris- and C_2v-symmetric tetra-adducts of C₇₀, which are the precursors of the mono- and bis-adduct final products.

Authors:

Cerón, Maira R. ^[1];

^[2]; Neti, Venkata S. Pavan K. ^[2]; Dunk, Paul W. ^[3];

^[2]

Univ. of Texas at El Paso, El Paso, TX (United States); Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States)
Univ. of Texas at El Paso, El Paso, TX (United States)
Florida State Univ., Tallahassee, FL (United States)

Publication Date:: Thu Dec 22 00:00:00 EST 2016

Research Org.:: Lawrence Livermore National Laboratory (LLNL), Livermore, CA (United States)

Sponsoring Org.:: USDOE

OSTI Identifier:: 1347677

Report Number(s):: LLNL-JRNL-715857
Journal ID: ISSN 0022-3263

Grant/Contract Number:: AC52-07NA27344

Resource Type:: Accepted Manuscript

Journal Name:: Journal of Organic Chemistry

Additional Journal Information:: Journal Volume: 82; Journal Issue: 2; Journal ID: ISSN 0022-3263

Publisher:: American Chemical Society

Country of Publication:: United States

Language:: English

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

Citation Formats


                    Cerón, Maira R., Castro, Edison, Neti, Venkata S. Pavan K., Dunk, Paul W., and Echegoyen, Luis A. Regiochemically controlled synthesis of a β-4-β' [70]fullerene bis-adduct.  United States: N. p., 2016. 
Web.  doi:10.1021/acs.joc.6b02301.

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                    Cerón, Maira R., Castro, Edison, Neti, Venkata S. Pavan K., Dunk, Paul W., & Echegoyen, Luis A. Regiochemically controlled synthesis of a β-4-β' [70]fullerene bis-adduct.  United States.  https://doi.org/10.1021/acs.joc.6b02301

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                    Cerón, Maira R., Castro, Edison, Neti, Venkata S. Pavan K., Dunk, Paul W., and Echegoyen, Luis A. Thu .  
"Regiochemically controlled synthesis of a β-4-β' [70]fullerene bis-adduct".  United States.  https://doi.org/10.1021/acs.joc.6b02301.  https://www.osti.gov/servlets/purl/1347677.

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@article{osti_1347677,

  title        = {Regiochemically controlled synthesis of a β-4-β' [70]fullerene bis-adduct},

  author       = {Cerón, Maira R. and Castro, Edison and Neti, Venkata S. Pavan K. and Dunk, Paul W. and Echegoyen, Luis A.},

  abstractNote = {A β-4-β' C70 bis-adduct regioisomer and an uncommon mono-adduct β-malonate C70 derivative were synthesized by using a Diels–Alder cycloaddition followed by an addition–elimination of bromo-ethylmalonate and a retro-Diels–Alder cycloaddition reaction. Here, we also report the regioselective synthesis and spectroscopic characterization of Cs-symmetric tris- and C2v-symmetric tetra-adducts of C70, which are the precursors of the mono- and bis-adduct final products.},

  doi          = {10.1021/acs.joc.6b02301},

  journal      = {Journal of Organic Chemistry},

  number       = 2,

  volume       = 82,

  place        = {United States},

  year         = {Thu Dec 22 00:00:00 EST 2016},

  month        = {Thu Dec 22 00:00:00 EST 2016}

}

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https://doi.org/10.1021/acs.joc.6b02301

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Title: Regiochemically controlled synthesis of a β-4-β' [70]fullerene bis-adduct

Abstract

Citation Formats

The Chemistry of the Fullerenes: An Overview journal, August 1993

Principles of Fullerene Reactivity book, January 1999

Single Isomer of Indene-C 70 Bisadduct—Isolation and Performance in Bulk Heterojunction Solar Cells journal, February 2014

A molecular nematic liquid crystalline material for high-performance organic photovoltaics journal, January 2015

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Fullerene Bisadducts for Enhanced Open-Circuit Voltages and Efficiencies in Polymer Solar Cells journal, June 2008

Regioisomer effects of [70]fullerene mono-adduct acceptors in bulk heterojunction polymer solar cells journal, January 2017

Reducing Regioisomers of Fullerene-Bisadducts by Tether-Directed Remote Functionalization: Investigation of Electronically and Sterically Isomeric Effects on Bulk-Heterojunction Solar Cells journal, December 2013

Effects of dihydronaphthyl-based [60]fullerene bisadduct regioisomers on polymer solar cell performance journal, January 2012

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A single cis-2 regioisomer of ethylene-tethered indene dimer–fullerene adduct as an electron-acceptor in polymer solar cells journal, January 2015

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Tether-Directed Remote Functionalization of Buckminsterfullerene: Regiospecific Hexaadduct Formation journal, December 1994

A Highly Symmetric Sixfold Cycloaddition Product of Fullerene C60 journal, January 1995

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Multiple Cyclopropanations of C70. Synthesis and characterization of bis-, tris-, and tetrakis-adducts and chiroptical properties of bis-adducts with chiral addends, including a recommendation for the configurational description of fullerene derivatives w journal, November 1995

Tethered Bisadducts of C 60 and C 70 with Addends on a Common Hexagonal Face and a 12-Membered Hole in the Fullerene Cage journal, June 2015

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First tether-directed regioselective bis-functionalisation of C70: effects of cation complexation on the redox properties of diastereoisomeric fullerene crown ether conjugates journal, January 2000

Cyclopropanierung von Fullerenen journal, August 1993

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Tether-Directed Bisfunctionalization Reactions of C 60 and C 70 journal, April 2015

Retrocyclopropanation Reactions of Fullerenes: Complete Product Analyses journal, June 2003

Synthesis, Electrochemistry and Self-Assembled Monolayers of Novel Tetrathiafulvalene (TTF) and π-Extended TTF ( e x TTF) Disulfides journal, October 2003

Selective Electrolytic Removal of Bis(alkoxycarbonyl)methano Addends from C60 Bis-adducts and Electrochemical Stability of C70 Derivatives journal, June 2000

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The Chemistry of the Fullerenes: An Overview
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Principles of Fullerene Reactivity
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A molecular nematic liquid crystalline material for high-performance organic photovoltaics
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Effects of Alkyl Chain Length and Substituent Pattern of Fullerene Bis-Adducts on Film Structures and Photovoltaic Properties of Bulk Heterojunction Solar Cells
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Tether-Directed Remote Functionalization of Buckminsterfullerene: Regiospecific Hexaadduct Formation
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A Topochemically Controlled, Regiospecific Fullerene Bisfunctionalization
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Multiple Cyclopropanations of C70. Synthesis and characterization of bis-, tris-, and tetrakis-adducts and chiroptical properties of bis-adducts with chiral addends, including a recommendation for the configurational description of fullerene derivatives w
journal, November 1995

Tethered Bisadducts of C ₆₀ and C ₇₀ with Addends on a Common Hexagonal Face and a 12-Membered Hole in the Fullerene Cage
journal, June 2015

Achiral and Chiral Higher Adducts of C70 byBingel Cyclopropanation
journal, February 1999

Supramolecular Fullerene Chemistry: A Comprehensive Study of Cyclophane-Type Mono- and Bis-Crown Ether Conjugates of C70
journal, July 2002

High-yield, regiospecific bis-functionalization of C ₇₀ using a Diels–Alder reaction in molten anthracene
journal, January 2014

First tether-directed regioselective bis-functionalisation of C70: effects of cation complexation on the redox properties of diastereoisomeric fullerene crown ether conjugates
journal, January 2000

Cyclopropanierung von Fullerenen
journal, August 1993

Biscyclopropanation of C70
journal, August 1995

Tether-Directed Bisfunctionalization Reactions of C ₆₀ and C ₇₀
journal, April 2015

Retrocyclopropanation Reactions of Fullerenes: Complete Product Analyses
journal, June 2003

Synthesis, Electrochemistry and Self-Assembled Monolayers of Novel Tetrathiafulvalene (TTF) and π-Extended TTF ( e x TTF) Disulfides
journal, October 2003

Selective Electrolytic Removal of Bis(alkoxycarbonyl)methano Addends from C60 Bis-adducts and Electrochemical Stability of C70 Derivatives
journal, June 2000

Unexpected and selective formation of an (e,e,e,e)-tetrakis-[60]fullerene derivative via electrolytic retro-cyclopropanation of a D _2h -hexakis-[60]fullerene adduct
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