Modification of alkyne-functionalized asymmetric phthalocyanines by CuI-catalyzed azide-alkyne cycloaddition
- Authors:
- Publication Date:
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1245655
- Grant/Contract Number:
- SC0001084
- Resource Type:
- Publisher's Accepted Manuscript
- Journal Name:
- Tetrahedron
- Additional Journal Information:
- Journal Name: Tetrahedron Journal Volume: 71 Journal Issue: 48; Journal ID: ISSN 0040-4020
- Publisher:
- Elsevier
- Country of Publication:
- United Kingdom
- Language:
- English
Citation Formats
Chen, Xiaochun, Lu, Chin-Wei, Huang, Yiming, and McGrath, Dominic V. Modification of alkyne-functionalized asymmetric phthalocyanines by CuI-catalyzed azide-alkyne cycloaddition. United Kingdom: N. p., 2015.
Web. doi:10.1016/j.tet.2015.09.074.
Chen, Xiaochun, Lu, Chin-Wei, Huang, Yiming, & McGrath, Dominic V. Modification of alkyne-functionalized asymmetric phthalocyanines by CuI-catalyzed azide-alkyne cycloaddition. United Kingdom. https://doi.org/10.1016/j.tet.2015.09.074
Chen, Xiaochun, Lu, Chin-Wei, Huang, Yiming, and McGrath, Dominic V. Tue .
"Modification of alkyne-functionalized asymmetric phthalocyanines by CuI-catalyzed azide-alkyne cycloaddition". United Kingdom. https://doi.org/10.1016/j.tet.2015.09.074.
@article{osti_1245655,
title = {Modification of alkyne-functionalized asymmetric phthalocyanines by CuI-catalyzed azide-alkyne cycloaddition},
author = {Chen, Xiaochun and Lu, Chin-Wei and Huang, Yiming and McGrath, Dominic V.},
abstractNote = {},
doi = {10.1016/j.tet.2015.09.074},
journal = {Tetrahedron},
number = 48,
volume = 71,
place = {United Kingdom},
year = {Tue Dec 01 00:00:00 EST 2015},
month = {Tue Dec 01 00:00:00 EST 2015}
}
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https://doi.org/10.1016/j.tet.2015.09.074
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Works referenced in this record:
Preparation of monohydroxyphthalocyanines and their use in the synthesis of heteronuclear complexes
journal, September 2008
- Tolbin, Alexander Yu.; Tomilova, Larisa G.
- Mendeleev Communications, Vol. 18, Issue 5
Click Chemistry: Diverse Chemical Function from a Few Good Reactions
journal, June 2001
- Kolb, Hartmuth C.; Finn, M. G.; Sharpless, K. Barry
- Angewandte Chemie International Edition, Vol. 40, Issue 11, p. 2004-2021
Synthesis and Photodynamic Activity of Novel Asymmetrically Substituted Fluorinated Phthalocyanines
journal, September 2005
- Sharman, Wesley M.; van Lier, Johan E.
- Bioconjugate Chemistry, Vol. 16, Issue 5
Organic photovoltaic cells with near infrared absorption spectrum
journal, December 2007
- Dai, Jiguang; Jiang, Xiaoxia; Wang, Haibo
- Applied Physics Letters, Vol. 91, Issue 25
Phthalocyanines: The Need for Selective Synthetic Approaches
journal, August 2000
- de la Torre, Gema; Claessens, Christian G.; Torres, Tomás
- European Journal of Organic Chemistry, Vol. 2000, Issue 16
Role of Structural Factors in the Nonlinear Optical Properties of Phthalocyanines and Related Compounds
journal, September 2004
- de la Torre, Gema; Vázquez, Purificación; Agulló-López, F.
- Chemical Reviews, Vol. 104, Issue 9
Parallel synthesis of unsymmetrically substituted tetraphenyl porphyrins on Wang resin
journal, June 2003
- Shi, Baolu; Scobie, Martin; Boyle, Ross W.
- Tetrahedron Letters, Vol. 44, Issue 27
Axially modified gallium phthalocyanines and naphthalocyanines for optical limiting
journal, January 2005
- Chen, Yu; Hanack, Michael; Araki, Yasuyuki
- Chemical Society Reviews, Vol. 34, Issue 6
Organic Field-Effect Transistors—The Breakthrough at Last
journal, March 2001
- Kraft, Arno
- ChemPhysChem, Vol. 2, Issue 3
Asymmetric Phthalocyanine Synthesis by ROMP-Capture-Release
journal, May 2009
- Chen, Xiaochun; Salmon, III, Thaddeus R.; McGrath, Dominic V.
- Organic Letters, Vol. 11, Issue 10
Exploiting domino enyne metathesis mechanisms for skeletal diversity generation
journal, January 2008
- Spandl, Richard J.; Rudyk, Hèléne; Spring, David R.
- Chemical Communications, Issue 26
Facile Decoration of Functionalized Single-Wall Carbon Nanotubes with Phthalocyanines via “Click Chemistry”
journal, July 2008
- Campidelli, Stéphane; Ballesteros, Beatriz; Filoramo, Arianna
- Journal of the American Chemical Society, Vol. 130, Issue 34
Phosphonic Acid Functionalized Asymmetric Phthalocyanines: Synthesis, Modification of Indium Tin Oxide, and Charge Transfer
journal, December 2011
- Polaske, Nathan W.; Lin, Hsiao-Chu; Tang, Anna
- Langmuir, Vol. 27, Issue 24
Synthesis of Degradable Model Networks via ATRP and Click Chemistry
journal, May 2006
- Johnson, Jeremiah A.; Lewis, Danielle R.; Díaz, David D.
- Journal of the American Chemical Society, Vol. 128, Issue 20
Multichromophoric Phthalocyanine-(Perylenediimide) 8 Molecules: A Photophysical Study
journal, July 2010
- Albert-Seifried, Sebastian; Finlayson, Chris E.; Laquai, Frederic
- Chemistry - A European Journal, Vol. 16, Issue 33
Derivatization and in situ metallation of phthalocyanines using click chemistry
journal, November 2009
- Yılmaz, Yusuf; Kasım Şener, M.; Erden, İbrahim
- Polyhedron, Vol. 28, Issue 16
Organic-Based Photovoltaics: Toward Low-Cost Power Generation
journal, January 2005
- Shaheen, Sean E.; Ginley, David S.; Jabbour, Ghassan E.
- MRS Bulletin, Vol. 30, Issue 1, p. 10-19
Titanyl Phthalocyanine/C 60 Heterojunctions: Band-Edge Offsets and Photovoltaic Device Performance
journal, February 2008
- Brumbach, Michael; Placencia, Diogenes; Armstrong, Neal R.
- The Journal of Physical Chemistry C, Vol. 112, Issue 8
A Novel Modular Approach to Triazole-Functionalized Phthalocyanines Using Click Chemistry
journal, January 2009
- Juríček, Michal; Kouwer, Paul H. J.; Rehák, Juraj
- The Journal of Organic Chemistry, Vol. 74, Issue 1
A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes
journal, July 2002
- Rostovtsev, Vsevolod V.; Green, Luke G.; Fokin, Valery V.
- Angewandte Chemie International Edition, Vol. 41, Issue 14, p. 2596-2599
Postfunctionalization of Helical Polyisocyanopeptides with Phthalocyanine Chromophores by “Click Chemistry”
journal, June 2012
- López-Duarte, Ismael; Martínez-Díaz, M. Victoria; Schwartz, Erik
- ChemPlusChem, Vol. 77, Issue 8
Electron-Transfer Processes in Zinc Phthalocyanine–Phosphonic Acid Monolayers on ITO: Characterization of Orientation and Charge-Transfer Kinetics by Waveguide Spectroelectrochemistry
journal, April 2012
- Lin, Hsiao-Chu; Polaske, Nathan W.; Oquendo, Luis E.
- The Journal of Physical Chemistry Letters, Vol. 3, Issue 9
A survey on the functionalization of single-walled nanotubes. The chemical attachment of phthalocyanine moieties
journal, May 2003
- Torre, Gema de la; Blau, Werner; Torres, Tomas
- Nanotechnology, Vol. 14, Issue 7
Ex Post Glycoconjugation of Phthalocyanines
journal, April 2010
- Berthold, Herwig J.; Franke, Stephan; Thiem, Joachim
- The Journal of Organic Chemistry, Vol. 75, Issue 11
Non-aggregating octasubstituted dendritic phthalocyanines
journal, April 2003
- Kernag, Casey A.; McGrath, Dominic V.
- Chemical Communications, Issue 9
A Novel Potent Nicotinamide Phosphoribosyltransferase Inhibitor Synthesized via Click Chemistry
journal, January 2010
- Colombano, Giampiero; Travelli, Cristina; Galli, Ubaldina
- Journal of Medicinal Chemistry, Vol. 53, Issue 2
25th Anniversary Article: Organic Field-Effect Transistors: The Path Beyond Amorphous Silicon
journal, January 2014
- Sirringhaus, Henning
- Advanced Materials, Vol. 26, Issue 9
Structure-Function Relationships in Unsymmetrical Zinc Phthalocyanines for Dye-Sensitized Solar Cells
journal, May 2009
- Cid, Juan-José; García-Iglesias, Miguel; Yum, Jun-Ho
- Chemistry - A European Journal, Vol. 15, Issue 20
Synthesis of phthalocyanines with one sulfonic acid, carboxylic acid, or amino group
journal, July 1995
- Kliesch, Holger; Weitemeyer, Andrea; Müller, Silke
- Liebigs Annalen, Vol. 1995, Issue 7
SWNT ensembles with porphyrins and phthalocyanines: new architectures for energy conversion
journal, April 2009
- de la Torre, Gema
- Journal of Porphyrins and Phthalocyanines, Vol. 13, Issue 04n05
Porphyrins and phthalocyanines as materials for optical limiting
journal, March 2004
- Calvete, Mario; Yang, Guo Ying; Hanack, Michael
- Synthetic Metals, Vol. 141, Issue 3
Zn-porphyrin/Zn-phthalocyanine dendron for SWNT functionalisation
journal, January 2009
- Le Ho, Khanh Hy; Rivier, Lucie; Jousselme, Bruno
- Chemical Communications, Vol. 46, Issue 46
Frustration of Condensed Phase Aggregation of Naphthalocyanine by Dendritic Site-Isolation
journal, June 2010
- Chen, Xiaochun; Fernando, Nilmi; McGrath, Dominic V.
- Macromolecules, Vol. 43, Issue 13
Molecular Engineering of Peripherally And Axially Modified Phthalocyanines for Optical Limiting and Nonlinear Optics
journal, January 2003
- O’Flaherty, S. M.; Hold, S. V.; Cook, M. J.
- Advanced Materials, Vol. 15, Issue 1
Organic Photovoltaic Cells Based On Solvent-Annealed, Textured Titanyl Phthalocyanine/C60 Heterojunctions
journal, June 2009
- Placencia, Diogenes; Wang, Weining; Shallcross, R. Clayton
- Advanced Functional Materials, Vol. 19, Issue 12, p. 1913-1921
Novel non-aggregated unsymmetrical metallophthalocyanines for second-order non-linear optics
journal, January 1997
- Tian, Minquan; Wada, Tatsuo; Kimura-Suda, Hiromi
- Journal of Materials Chemistry, Vol. 7, Issue 6
Broadening the absorption of conjugated polymers by “click” functionalization with phthalocyanines
journal, January 2011
- Campo, Bert J.; Duchateau, Jan; Ganivet, Carolina R.
- Dalton Transactions, Vol. 40, Issue 15
Control of product distribution in the domino metathesis reactions of N-alkynyl 2-azabicyclo[2.2.1]hept-5-en-3-ones. A convenient synthesis of functionalized γ-lactams and indolizidinones
journal, January 2004
- Arjona, Odón; Csákÿ, Aurelio G.; León, Vanessa
- Tetrahedron Letters, Vol. 45, Issue 3
Synthesis and characterization of novel tetra terminal alkynyl-substituted phthalocyanines and their star polymers via click reaction
journal, August 2013
- Dinçer, Hatice; Mert, Humeyra; Şen, Betül Nur
- Dyes and Pigments, Vol. 98, Issue 2
Combining Ring-Opening Metathesis Polymerization (ROMP) with Sharpless-Type “Click” Reactions: An Easy Method for the Preparation of Side Chain Functionalized Poly(oxynorbornenes)
journal, December 2004
- Binder, Wolfgang H.; Kluger, Christian
- Macromolecules, Vol. 37, Issue 25
Synthesis of novel unsymmetrical monoaminated phthalocyanines
journal, November 1995
- Sastre, Angela; Torres, Tomas; Hanack, Michael
- Tetrahedron Letters, Vol. 36, Issue 46
Unsymmetrically functionalized phthalocyanines as versatile platforms for the preparation of molecular materials
journal, April 2009
- Victoria Martínez-Díaz, M.; Díaz Díaz, David
- Journal of Porphyrins and Phthalocyanines, Vol. 13, Issue 04n05
Asymmetrical, Water-Soluble Phthalocyanine Dyes for Covalent Labeling of Oligonucleotides
journal, November 2002
- Hammer, Robert P.; Owens, Clyde V.; Hwang, Seok-Hwan
- Bioconjugate Chemistry, Vol. 13, Issue 6
Solid-Phase Synthesis of Asymmetrically Substituted “AB 3 -Type” Phthalocyanines
journal, May 2008
- Erdem, S. Sibel; Nesterova, Irina V.; Soper, Steven A.
- The Journal of Organic Chemistry, Vol. 73, Issue 13
Post-modification of helical dipeptido polyisocyanides using the ‘click’ reaction
journal, January 2008
- Kitto, Heather J.; Schwartz, Erik; Nijemeisland, Marlies
- Journal of Materials Chemistry, Vol. 18, Issue 46
Photodynamic Therapy: Porphyrins and Phthalocyanines as Photosensitizers
journal, January 2008
- Moreira, Leonardo Marmo; Vieira dos Santos, Fábio; Lyon, Juliana Pereira
- Australian Journal of Chemistry, Vol. 61, Issue 10
Synthesis of Benzene-centered Trinuclear Phthalocyanines by Triple-click Chemistry
journal, April 2010
- Das, Banibrata; Umeda, Masashi; Tokunaga, Etsuko
- Chemistry Letters, Vol. 39, Issue 4
Hydroxyphthalocyanines as Potential Photodynamic Agents for Cancer Therapy
journal, May 1998
- Hu, Mougang; Brasseur, Nicole; Yildiz, S. Zeki
- Journal of Medicinal Chemistry, Vol. 41, Issue 11
Peripheral Substitution of a Near-IR-Absorbing Soluble Phthalocyanine Using “Click” Chemistry
journal, June 2011
- Mayukh, Mayank; Lu, Chin-Wei; Hernandez, Edgardo
- Chemistry - A European Journal, Vol. 17, Issue 30
Catalytic Ring Closing Metathesis of Dienynes: Construction of Fused Bicyclic [ n . m.0] Rings
journal, January 1996
- Kim, Soong-Hoon; Zuercher, William J.; Bowden, Ned B.
- The Journal of Organic Chemistry, Vol. 61, Issue 3
Phthalocyanines as Active Materials for Optical Limiting
journal, October 2001
- Dini, Danilo; Barthel, Markus; Hanack, Michael
- European Journal of Organic Chemistry, Vol. 2001, Issue 20
Efficient covalent functionalisation of carbon nanotubes: the use of “click chemistry”
journal, January 2011
- Clavé, Guillaume; Campidelli, Stéphane
- Chemical Science, Vol. 2, Issue 10
Low bias stress and reduced operating voltage in SnCl 2 Pc based n-type organic field-effect transistors
journal, May 2014
- Md. Obaidulla, Sk.; Goswami, D. K.; Giri, P. K.
- Applied Physics Letters, Vol. 104, Issue 21
Novel 1,3-diene synthesis from alkyne and ethylene by ruthenium-catalyzed enyne metathesis
journal, July 1999
- Kinoshita, Atsushi; Sakakibara, Norikazu; Mori, Miwako
- Tetrahedron, Vol. 55, Issue 27
Phthalocyanines: From outstanding electronic properties to emerging applications
journal, January 2008
- Claessens, Christian G.; Hahn, Uwe; Torres, Tomás
- The Chemical Record, Vol. 8, Issue 2
Modification of Symmetrically Substituted Phthalocyanines Using Click Chemistry: Phthalocyanine Nanostructures by Nanoimprint Lithography
journal, August 2009
- Chen, Xiaochun; Thomas, Jayan; Gangopadhyay, Palash
- Journal of the American Chemical Society, Vol. 131, Issue 38
Recent Progress on Enyne Metathesis: Its Application to Syntheses of Natural Products and Related Compounds
journal, March 2010
- Mori, Miwako
- Materials, Vol. 3, Issue 3
Parallel Synthesis of Terminal Alkynes Using a ROMPgel-Supported Ethyl 1-Diazo-2-oxopropylphosphonate
journal, March 2004
- Barrett, Anthony G. M.; Hopkins, Brian T.; Love, Andrew C.
- Organic Letters, Vol. 6, Issue 5
Chromatographic Separation of the Four Possible Structural Isomers of a Tetrasubstituted Phthalocyanine: Tetrakis(2-ethylhexyloxy)phthalocyaninatonickel(II)
journal, October 1993
- Hanack, Michael; Schmid, Gabriele; Sommerauer, Michael
- Angewandte Chemie International Edition in English, Vol. 32, Issue 10
Peptidotriazoles on Solid Phase [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides
journal, May 2002
- Tornøe, Christian W.; Christensen, Caspar; Meldal, Morten
- The Journal of Organic Chemistry, Vol. 67, Issue 9, p. 3057-3064
Solution and Thin-Film Aggregation Studies of Octasubstituted Dendritic Phthalocyanines
journal, May 2009
- Kernag, Casey A.; Mcgrath, Dominic V.
- Israel Journal of Chemistry, Vol. 49, Issue 1
Synthesis of covalently linked binuclear clamshell phthalocyanine by double-click reaction
journal, January 2008
- Yoshiyama, Hideyuki; Shibata, Norio; Sato, Takefumi
- Organic & Biomolecular Chemistry, Vol. 6, Issue 24
Microwave-Assisted Synthesis of Triazole-Linked Phthalocyanine-Peptide Conjugates as Potential Photosensitizers for Photodynamic Therapy
journal, January 2013
- Sokolova, Nadezhda; Schotten, Theo; Berthold, Herwig
- Synthesis, Vol. 45, Issue 04
New route to unsymmetrical phthalocyanine analogs by the use of structurally distorted subphthalocyanines
journal, December 1990
- Kobayashi, Nagao; Kondo, Ryoko; Nakajima, Shinichiro
- Journal of the American Chemical Society, Vol. 112, Issue 26
Alkynyl-substituted phthalocyanines: versatile building blocks for molecular materials synthesis
journal, September 2006
- Bottari, Giovanni; Díaz, David D.; Torres, Tomás
- Journal of Porphyrins and Phthalocyanines, Vol. 10, Issue 09
Click chemistry: the emerging role of the azide-alkyne Huisgen dipolar addition in the preparation of substituted tetrapyrrolic derivatives
journal, July 2011
- Dumoulin, Fabienne; Ahsen, Vefa
- Journal of Porphyrins and Phthalocyanines, Vol. 15, Issue 07n08