skip to main content
DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

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

Authors:
 [1];  [1];  [2];  [3];  [1];  [4]; ORCiD logo [1]
  1. Institute of Organic ChemistryJustus-Liebig-University Heinrich-Buff-Ring 17 35392 Giessen Germany
  2. Department of Chemical SciencesUniversity of Padova, Via Marzolo 1-35131 Padova Italy
  3. Institute of Inorganic ChemistryJustus-Liebig-University Heinrich-Buff-Ring 17 35392 Giessen Germany
  4. Department of ChemistryMemorial University of Newfoundland St. John's NL A1B 3X7 Canada
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1400567
Grant/Contract Number:  
AC02-76SF00515
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Angewandte Chemie
Additional Journal Information:
Journal Name: Angewandte Chemie Journal Volume: 128 Journal Issue: 32; Journal ID: ISSN 0044-8249
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/ange.201602201.
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. doi:10.1002/ange.201602201.
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. doi:10.1002/ange.201602201.
@article{osti_1400567,
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 = {},
doi = {10.1002/ange.201602201},
journal = {Angewandte Chemie},
number = 32,
volume = 128,
place = {Germany},
year = {2016},
month = {3}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: 10.1002/ange.201602201

Save / Share:

Works referenced in this record:

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

  • Lai, Rebecca Y.; Fleming, James J.; Merner, Brad L.
  • The Journal of Physical Chemistry A, Vol. 108, Issue 3
  • DOI: 10.1021/jp0367981

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

  • Pérez-Bolívar, César; Takizawa, Shin-ya; Nishimura, Go
  • Chemistry - A European Journal, Vol. 17, Issue 33
  • DOI: 10.1002/chem.201100707

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

  • Nayak, Susanta K.; Sathishkumar, Ranganathan; Row, T. N. Guru
  • CrystEngComm, Vol. 12, Issue 10
  • DOI: 10.1039/c001190h

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

  • Bis, Joanna A.; Vishweshwar, Peddy; Middleton, Richard A.
  • Crystal Growth & Design, Vol. 6, Issue 4
  • DOI: 10.1021/cg0680024

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

  • Borch, Richard F.
  • Journal of the American Chemical Society, Vol. 90, Issue 19
  • DOI: 10.1021/ja01021a062

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

  • Borch, Richard F.
  • The Journal of Organic Chemistry, Vol. 34, Issue 3
  • DOI: 10.1021/jo01255a031

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

  • Bodwell, Graham J.; Fleming, James J.; Mannion, Michael R.
  • The Journal of Organic Chemistry, Vol. 65, Issue 17
  • DOI: 10.1021/jo0007027

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

  • Schwertfeger, Hartmut; Fokin, Andrey A.; Schreiner, Peter R.
  • Angewandte Chemie, Vol. 120, Issue 6
  • DOI: 10.1002/ange.200701684

A Hierarchy of Homodesmotic Reactions for Thermochemistry
journal, February 2009

  • Wheeler, Steven E.; Houk, Kendall N.; Schleyer, Paul v. R.
  • Journal of the American Chemical Society, Vol. 131, Issue 7
  • DOI: 10.1021/ja805843n

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

  • Bodwell, Graham J.; Miller, David O.; Vermeij, Rudolf J.
  • Organic Letters, Vol. 3, Issue 13
  • DOI: 10.1021/ol016053i

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

  • Li, Fei Hua; Fabbri, Jason D.; Yurchenko, Raisa I.
  • Langmuir, Vol. 29, Issue 31
  • DOI: 10.1021/la401781e

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

  • Schleyer, Paul von Ragué; Maerker, Christoph; Dransfeld, Alk
  • Journal of the American Chemical Society, Vol. 118, Issue 26
  • DOI: 10.1021/ja960582d

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

  • Pereira Silva, Pedro S.; Castro, Ricardo A. E.; Melro, Elodie
  • Journal of Thermal Analysis and Calorimetry, Vol. 120, Issue 1
  • DOI: 10.1007/s10973-014-4289-y

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

  • Maria, Teresa M. R.; Castro, Ricardo A. E.; Bebiano, Suse S.
  • Crystal Growth & Design, Vol. 10, Issue 3
  • DOI: 10.1021/cg901160v

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

  • Toyoda, Toshihiro; Kasai, Nobutami; Misumi, Soichi
  • Bulletin of the Chemical Society of Japan, Vol. 58, Issue 8
  • DOI: 10.1246/bcsj.58.2348

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

  • Bilton, Clair; Howard, Judith A. K.; Laxmi Madhavi, N. N.
  • Chemical Communications, Issue 17
  • DOI: 10.1039/a905025f

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

  • Yang, Yixi; Mannion, Michael R.; Dawe, Louise N.
  • The Journal of Organic Chemistry, Vol. 77, Issue 1
  • DOI: 10.1021/jo201013q

Über Tertiäre Oxoniumsalze, I
journal, January 1937

  • Meerwein, Hans; Hinz, Gerhard; Hofmann, Paul
  • Journal für Praktische Chemie, Vol. 147, Issue 10-12
  • DOI: 10.1002/prac.19371471001

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

  • Vermeij, Rudolf J.; Miller, David O.; Dawe, Louise N.
  • Australian Journal of Chemistry, Vol. 63, Issue 12
  • DOI: 10.1071/CH10356

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

  • Kono, Shozo; Koizumi, Satoshi
  • e-Journal of Surface Science and Nanotechnology, Vol. 7
  • DOI: 10.1380/ejssnt.2009.660

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

  • Merner, Bradley L.; Dawe, Louise N.; Bodwell, Graham J.
  • Angewandte Chemie International Edition, Vol. 48, Issue 30
  • DOI: 10.1002/anie.200806363

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

  • Narasimha, Karthik Thimmavajjula; Ge, Chenhao; Fabbri, Jason D.
  • Nature Nanotechnology, Vol. 11, Issue 3
  • DOI: 10.1038/nnano.2015.277

Organic electroluminescent diodes
journal, September 1987

  • Tang, C. W.; VanSlyke, S. A.
  • Applied Physics Letters, Vol. 51, Issue 12
  • DOI: 10.1063/1.98799

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

  • Yasutake, Mikio; Araki, Koji; Zhou, Ming
  • European Journal of Organic Chemistry, Vol. 2003, Issue 7
  • DOI: 10.1002/ejoc.200390190

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

  • Bowles, Faye L.; Mercado, Brandon Q.; Ghiassi, Kamran B.
  • Crystal Growth & Design, Vol. 13, Issue 10
  • DOI: 10.1021/cg401138g

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

  • Randel, Jason C.; Niestemski, Francis C.; Botello-Mendez, Andrés R.
  • Nature Communications, Vol. 5, Issue 1
  • DOI: 10.1038/ncomms5877

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

  • Irngartinger, Hermann; Hekeler, Jürgen; Lang, Barbara Margarete
  • Chemische Berichte, Vol. 116, Issue 2
  • DOI: 10.1002/cber.19831160214

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

  • Anderson, Arthur G.; Steckler, Bernard M.
  • Journal of the American Chemical Society, Vol. 81, Issue 18
  • DOI: 10.1021/ja01527a046

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

  • Esteves de Castro, R. A.; Canotilho, João; Barbosa, Rui M.
  • Crystal Growth & Design, Vol. 7, Issue 3
  • DOI: 10.1021/cg0601857

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

  • Merner, Bradley L.; Dawe, Louise N.; Bodwell, Graham J.
  • Angewandte Chemie, Vol. 121, Issue 30
  • DOI: 10.1002/ange.200806363

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


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

  • Amoureux, J. P.; Foulon, M.
  • Acta Crystallographica Section B Structural Science, Vol. 43, Issue 5
  • DOI: 10.1107/S0108768187097465

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

  • Tkachenko, Boryslav A.; Fokina, Natalie A.; Chernish, Lesya V.
  • Organic Letters, Vol. 8, Issue 9
  • DOI: 10.1021/ol053136g

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

  • Zhuk, Tatyana S.; Koso, Tatyana; Pashenko, Alexander E.
  • Journal of the American Chemical Society, Vol. 137, Issue 20
  • DOI: 10.1021/jacs.5b01555

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

  • Schwertfeger, Hartmut; Fokin, Andrey A.; Schreiner, Peter R.
  • Angewandte Chemie International Edition, Vol. 47, Issue 6
  • DOI: 10.1002/anie.200701684

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