[2](1,3)Adamantano[2](2,7)pyrenophane: A Hydrocarbon with a Large Dipole Moment

Kahl, Paul; Wagner, J. Philipp; Balestrieri, Ciro; Becker, Jonathan; Hausmann, Heike; Bodwell, Graham J.; Schreiner, Peter R.

doi:10.1002/anie.201602201

Title: [2](1,3)Adamantano[2](2,7)pyrenophane: A Hydrocarbon with a Large Dipole Moment

Abstract

Abstract The fusion of the sp ³ ‐hybridized parent diamondoid adamantane with the sp ² ‐hybridized pyrene results in a hybrid structure with a very large dipole moment which arises from bending the pyrene moiety. Presented herein is the synthesis, study of the electronic and optical properties, as well as the dynamic behavior of this new hydrocarbon.

Authors:

Kahl, Paul ^[1]; Wagner, J. Philipp ^[1]; Balestrieri, Ciro ^[2]; Becker, Jonathan ^[3]; Hausmann, Heike ^[1]; Bodwell, Graham J. ^[4];

^[1]

Institute of Organic Chemistry Justus-Liebig-University Heinrich-Buff-Ring 17 35392 Giessen Germany
Department of Chemical Sciences University of Padova, Via Marzolo 1-35131 Padova Italy
Institute of Inorganic Chemistry Justus-Liebig-University Heinrich-Buff-Ring 17 35392 Giessen Germany
Department of Chemistry Memorial University of Newfoundland St. John's NL A1B 3X7 Canada

Publication Date:: Fri Jul 01 00:00:00 EDT 2016

Sponsoring Org.:: USDOE

OSTI Identifier:: 1401695

Grant/Contract Number:: AC02-76SF00515

Resource Type:: Publisher's Accepted Manuscript

Journal Name:: Angewandte Chemie (International Edition)

Additional Journal Information:: Journal Name: Angewandte Chemie (International Edition) Journal Volume: 55 Journal Issue: 32; Journal ID: ISSN 1433-7851

Publisher:: Wiley Blackwell (John Wiley & Sons)

Country of Publication:: Germany

Language:: English

Citation Formats


                    Kahl, Paul, Wagner, J. Philipp, Balestrieri, Ciro, Becker, Jonathan, Hausmann, Heike, Bodwell, Graham J., and Schreiner, Peter R. [2](1,3)Adamantano[2](2,7)pyrenophane: A Hydrocarbon with a Large Dipole Moment.  Germany: N. p., 2016. 
Web.  doi:10.1002/anie.201602201.

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                    Kahl, Paul, Wagner, J. Philipp, Balestrieri, Ciro, Becker, Jonathan, Hausmann, Heike, Bodwell, Graham J., & Schreiner, Peter R. [2](1,3)Adamantano[2](2,7)pyrenophane: A Hydrocarbon with a Large Dipole Moment.  Germany.  https://doi.org/10.1002/anie.201602201

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                    Kahl, Paul, Wagner, J. Philipp, Balestrieri, Ciro, Becker, Jonathan, Hausmann, Heike, Bodwell, Graham J., and Schreiner, Peter R. Fri .  
"[2](1,3)Adamantano[2](2,7)pyrenophane: A Hydrocarbon with a Large Dipole Moment".  Germany.  https://doi.org/10.1002/anie.201602201.

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@article{osti_1401695,

  title        = {[2](1,3)Adamantano[2](2,7)pyrenophane: A Hydrocarbon with a Large Dipole Moment},

  author       = {Kahl, Paul and Wagner, J. Philipp and Balestrieri, Ciro and Becker, Jonathan and Hausmann, Heike and Bodwell, Graham J. and Schreiner, Peter R.},

  abstractNote = {Abstract The fusion of the sp 3 ‐hybridized parent diamondoid adamantane with the sp 2 ‐hybridized pyrene results in a hybrid structure with a very large dipole moment which arises from bending the pyrene moiety. Presented herein is the synthesis, study of the electronic and optical properties, as well as the dynamic behavior of this new hydrocarbon.},

  doi          = {10.1002/anie.201602201},

  journal      = {Angewandte Chemie (International Edition)},

  number       = 32,

  volume       = 55,

  place        = {Germany},

  year         = {Fri Jul 01 00:00:00 EDT 2016},

  month        = {Fri Jul 01 00:00:00 EDT 2016}

}

Copy to clipboard

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Title: [2](1,3)Adamantano[2](2,7)pyrenophane: A Hydrocarbon with a Large Dipole Moment

Abstract

Citation Formats

1,7-Dioxa[7](2,7)pyrenophane: The Pyrene Moiety Is More Bent than That of C70 journal, June 1999

Internal Dynamics of Dendritic Molecules Probed by Pyrene Excimer Formation journal, January 2012

Electrogenerated Chemiluminescence. 74. Photophysical, Electrochemical, and Electrogenerated Chemiluminescent Studies of Selected Nonplanar Pyrenophanes journal, January 2004

High-Efficiency Tris(8-hydroxyquinoline)aluminum (Alq3) Complexes for Organic White-Light-Emitting Diodes and Solid-State Lighting journal, July 2011

Directing role of functional groups in selective generation of C–H⋯π interactions: In situ cryo-crystallographic studies on benzyl derivatives journal, January 2010

Concomitant and Conformational Polymorphism, Conformational Isomorphism, and Phase Relationships in 4-Cyanopyridine·4,4‘-biphenol Cocrystals journal, April 2006

Alkoxycarbonium ions. The structure of O-alkylated esters journal, September 1968

Nitrilium salts. New method for the synthesis of secondary amines journal, March 1969

Nonplanar Aromatic Compounds. † 3. A Proposed New Strategy for the Synthesis of Buckybowls. Synthesis, Structure and Reactions of [7]-, [8]- and [9](2,7)Pyrenophanes journal, August 2000

New highly strained adamantanophanes journal, January 1993

The functionalization of nanodiamonds ( diamondoids ) as a key parameter of their easily controlled self-assembly in micro- and nanocrystals from the vapor phase journal, January 2015

“Diamonds are a chemist's best friend”: die großen Geschwister des Adamantans journal, January 2008

A Hierarchy of Homodesmotic Reactions for Thermochemistry journal, February 2009

Nonplanar Aromatic Compounds. 6. [2]Paracyclo[2](2,7)pyrenophane. A Novel Strained Cyclophane and a First Step on the Road to a “Vögtle” Belt † journal, June 2001

Negative electron affinity of diamond and its application to high voltage vacuum power switches: NEA of diamond and its application to a high voltage vacuum power switch journal, October 2013

Covalent Attachment of Diamondoid Phosphonic Acid Dichlorides to Tungsten Oxide Surfaces journal, July 2013

Nucleus-Independent Chemical Shifts: A Simple and Efficient Aromaticity Probe journal, January 1996

Structural evidence of polymorphism and conformational isomorphism of a somewhat flexible molecule: m-anisic acid journal, December 2014

Polymorphism of trans -1,4-Cyclohexanediol: Conformational Isomorphism journal, March 2010

The Crystal and Molecular Structure of syn -[2.2](1,4)Anthracenophane and Its Photoisomer journal, August 1985

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Stilbenoid Dimers: Effect of Conjugation Length and Relative Chromophore Orientation journal, January 1998

Crystal Structure of Cyclophanes book, January 1983

When is a polymorph not a polymorph? Helical trimeric O–H···O synthons in trans-1,4-diethynylcyclohexane-1,4-diol journal, January 1999

Diamond as a unique high-tech electronic material: difficulties and prospects journal, October 2007

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Organic electroluminescent diodes journal, September 1987

Molecular conformation of crystalline polymers: some observations of conformational isomorphism journal, January 1975

Solid-State Structural Study of the Charge-Transfer Complexes of 5,7,9-Trimethyl- and 2,11,20-Trithia[33](1,3,5)cyclophanes journal, March 2003

Ordered Structures from Crystalline Carbon Disulfide Solvates of the Nano-Tubular Fullerenes D 5h (1)-C 90 and D 5h -C 70 journal, August 2013

Unconventional molecule-resolved current rectification in diamondoid–fullerene hybrids journal, September 2014

Preparation of 1,3-dialkynyladamantanes and their aluminum bromide-mediated cycloaddition adducts journal, January 1986

Kristall- und Molekularstruktur von zwei [24]Cyclophanen:[24](1,2,3,4)Cyclophan und [24](1,2,3,5)Cyclophan journal, February 1983

Azulene. VIII. A Study of the Visible Absorption Spectra and Dipole Moments of Some 1- and 1,3-Substituted Azulenes 1,2 journal, September 1959

Conformational Isomorphism of Organic Crystals: Racemic and Homochiral Atenolol journal, March 2007

Baicalein – main active flavonoid from Scutellaria baicalensis – voltammetric sensing in human samples using boron doped diamond electrode journal, September 2015

1,1,8,8-Tetramethyl[8](2,11)teropyrenophane: Half of an Aromatic Belt and a Segment of an (8,8) Single-Walled Carbon Nanotube journal, July 2009

Darstellung, Struktur und konformatives Verhalten gespannter Adamantanophane journal, June 1994

Nonplanar Aromatic Compounds. 8. 1 Synthesis, Crystal Structures, and Aromaticity Investigations of the 1, n -Dioxa[ n ](2,7)pyrenophanes. How Does Bending Affect the Cyclic π-Electron Delocalization of the Pyrene System? journal, March 2003

The microwave spectrum and dipole moment of azulene journal, November 1965

Considerations for a high-performance thermionic energy conversion device based on a negative electron affinity emitter journal, December 2007

Comparison between structural analyses of plastic and brittle crystals journal, October 1987

Functionalized Nanodiamonds Part 3: Thiolation of Tertiary/Bridgehead Alcohols ‖ journal, April 2006

Toward an Understanding of Diamond sp 2 -Defects with Unsaturated Diamondoid Oligomer Models journal, May 2015

Diamonds are a Chemist's Best Friend: Diamondoid Chemistry Beyond Adamantane journal, January 2008

Estimation of heats of formation of organic compounds by additivity methods journal, November 1993

1,7-Dioxa[7](2,7)pyrenophane: The Pyrene Moiety Is More Bent than That of C70
journal, June 1999

Internal Dynamics of Dendritic Molecules Probed by Pyrene Excimer Formation
journal, January 2012

Electrogenerated Chemiluminescence. 74. Photophysical, Electrochemical, and Electrogenerated Chemiluminescent Studies of Selected Nonplanar Pyrenophanes
journal, January 2004

High-Efficiency Tris(8-hydroxyquinoline)aluminum (Alq3) Complexes for Organic White-Light-Emitting Diodes and Solid-State Lighting
journal, July 2011

Directing role of functional groups in selective generation of C–H⋯π interactions: In situ cryo-crystallographic studies on benzyl derivatives
journal, January 2010

Concomitant and Conformational Polymorphism, Conformational Isomorphism, and Phase Relationships in 4-Cyanopyridine·4,4‘-biphenol Cocrystals
journal, April 2006

Alkoxycarbonium ions. The structure of O-alkylated esters
journal, September 1968

Nitrilium salts. New method for the synthesis of secondary amines
journal, March 1969

Nonplanar Aromatic Compounds. ^† 3. A Proposed New Strategy for the Synthesis of Buckybowls. Synthesis, Structure and Reactions of [7]-, [8]- and [9](2,7)Pyrenophanes
journal, August 2000

New highly strained adamantanophanes
journal, January 1993

The functionalization of nanodiamonds ( diamondoids ) as a key parameter of their easily controlled self-assembly in micro- and nanocrystals from the vapor phase
journal, January 2015

“Diamonds are a chemist's best friend”: die großen Geschwister des Adamantans
journal, January 2008

A Hierarchy of Homodesmotic Reactions for Thermochemistry
journal, February 2009

Nonplanar Aromatic Compounds. 6. [2]Paracyclo[2](2,7)pyrenophane. A Novel Strained Cyclophane and a First Step on the Road to a “Vögtle” Belt ^†
journal, June 2001

Negative electron affinity of diamond and its application to high voltage vacuum power switches: NEA of diamond and its application to a high voltage vacuum power switch
journal, October 2013

Covalent Attachment of Diamondoid Phosphonic Acid Dichlorides to Tungsten Oxide Surfaces
journal, July 2013

Nucleus-Independent Chemical Shifts: A Simple and Efficient Aromaticity Probe
journal, January 1996

Structural evidence of polymorphism and conformational isomorphism of a somewhat flexible molecule: m-anisic acid
journal, December 2014

Polymorphism of trans -1,4-Cyclohexanediol: Conformational Isomorphism
journal, March 2010

The Crystal and Molecular Structure of syn -[2.2](1,4)Anthracenophane and Its Photoisomer
journal, August 1985

Non-planar aromatic compounds. Part 4: Fine tuning the degree of bend in the pyrene moiety of [7](2,7)pyrenophanes by modifying the nature of the bridge
journal, April 2001

Stilbenoid Dimers: Effect of Conjugation Length and Relative Chromophore Orientation
journal, January 1998

Crystal Structure of Cyclophanes
book, January 1983

When is a polymorph not a polymorph? Helical trimeric O–H···O synthons in trans-1,4-diethynylcyclohexane-1,4-diol
journal, January 1999

Diamond as a unique high-tech electronic material: difficulties and prospects
journal, October 2007

Synthesis, Crystal Structure, and Resolution of [10](1,6)Pyrenophane: An Inherently Chiral [ n ]Cyclophane
journal, December 2011

Über Tertiäre Oxoniumsalze, I
journal, January 1937

Mixed [2.2]Cyclophanes of Pyrene and Benzene
journal, January 2010

New prospects and frontiers of nanodiamond clusters
journal, October 2007

Single-crystal X-ray diffraction analysis of pyrene II at 93K
journal, March 2000

UV laser induced changes to morphological, optical and electrical properties of conductive nanocrystalline diamond films
journal, September 2015

Images and Energy Distributions of Electrons Emitted from a Diamond pn-Junction Diode
journal, January 2009

1,1,8,8-Tetramethyl[8](2,11)teropyrenophane: Half of an Aromatic Belt and a Segment of an (8,8) Single-Walled Carbon Nanotube
journal, July 2009

Ultralow effective work function surfaces using diamondoid monolayers
journal, December 2015

Organic electroluminescent diodes
journal, September 1987

Molecular conformation of crystalline polymers: some observations of conformational isomorphism
journal, January 1975

Solid-State Structural Study of the Charge-Transfer Complexes of 5,7,9-Trimethyl- and 2,11,20-Trithia[33](1,3,5)cyclophanes
journal, March 2003

Ordered Structures from Crystalline Carbon Disulfide Solvates of the Nano-Tubular Fullerenes D _5h (1)-C ₉₀ and D _5h -C ₇₀
journal, August 2013

Unconventional molecule-resolved current rectification in diamondoid–fullerene hybrids
journal, September 2014

Preparation of 1,3-dialkynyladamantanes and their aluminum bromide-mediated cycloaddition adducts
journal, January 1986

Kristall- und Molekularstruktur von zwei [24]Cyclophanen:[24](1,2,3,4)Cyclophan und [24](1,2,3,5)Cyclophan
journal, February 1983

Azulene. VIII. A Study of the Visible Absorption Spectra and Dipole Moments of Some 1- and 1,3-Substituted Azulenes ^1,2
journal, September 1959

Conformational Isomorphism of Organic Crystals: Racemic and Homochiral Atenolol
journal, March 2007

Baicalein – main active flavonoid from Scutellaria baicalensis – voltammetric sensing in human samples using boron doped diamond electrode
journal, September 2015

1,1,8,8-Tetramethyl[8](2,11)teropyrenophane: Half of an Aromatic Belt and a Segment of an (8,8) Single-Walled Carbon Nanotube
journal, July 2009

Darstellung, Struktur und konformatives Verhalten gespannter Adamantanophane
journal, June 1994

Nonplanar Aromatic Compounds. 8. ¹ Synthesis, Crystal Structures, and Aromaticity Investigations of the 1, n -Dioxa[ n ](2,7)pyrenophanes. How Does Bending Affect the Cyclic π-Electron Delocalization of the Pyrene System?
journal, March 2003

The microwave spectrum and dipole moment of azulene
journal, November 1965

Considerations for a high-performance thermionic energy conversion device based on a negative electron affinity emitter
journal, December 2007

Comparison between structural analyses of plastic and brittle crystals
journal, October 1987

Functionalized Nanodiamonds Part 3: Thiolation of Tertiary/Bridgehead Alcohols ^‖
journal, April 2006

Toward an Understanding of Diamond sp ² -Defects with Unsaturated Diamondoid Oligomer Models
journal, May 2015

Diamonds are a Chemist's Best Friend: Diamondoid Chemistry Beyond Adamantane
journal, January 2008

Estimation of heats of formation of organic compounds by additivity methods
journal, November 1993