Organogold oligomers: Exploiting iClick and aurophilic cluster formation to prepare solution stable Au4 repeating units

Yang, Xi; Wang, Shanshan; Ghiviriga, Ion; Abboud, Khalil A.; Veige, Adam S.

doi:10.1039/C5DT00282F

Title: Organogold oligomers: Exploiting iClick and aurophilic cluster formation to prepare solution stable Au₄ repeating units

Abstract

A novel synthetic method to create gold based metallo–oligomers/polymers via the combination of inorganic click (iClick) with intermolecular aurophilic interactions is demonstrated. Complexes [PEt₃Au]₄(μ-N₃C₂C₆H₅) (1) and [PPhMe₂Au]₄3C₂C₆H₅) (2) and {[PEt₃Au]₄[(μ-N₃C₂)₂-9,9-dihexyl-9H-fluorene]}_n (8) have been synthesized via iClick. The tetranuclear structures of 1 and 2, induced by aurophilic bonding, are confirmed in the solid state through single crystal X-ray diffraction experiments and in solution via variable temperature NMR spectroscopy. The extended 1D structure of 8 is constructed by aurophilic induced self-assembly. ¹H DOSY NMR analysis reveals that the aurophilic bonds in 1, 2, and 8 are retained in the solution phase. The degree of polymerization within complex 8 is temperature and concentration dependent, as determined by ¹H DOSY NMR. The complex 8 is a rare example of a solution stable higher ordered structure linked by aurophilic interactions.

Authors:

Yang, Xi ^[1]; Wang, Shanshan ^[1]; Ghiviriga, Ion ^[1]; Abboud, Khalil A. ^[1]; Veige, Adam S. ^[1]

Univ. of Florida, Gainesville, FL (United States)

Publication Date:: Tue May 19 00:00:00 EDT 2015

Research Org.:: Univ. of Florida, Gainesville, FL (United States)

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

OSTI Identifier:: 1225601

Grant/Contract Number:: SC0010510

Resource Type:: Journal Article: Accepted Manuscript

Journal Name:: Dalton Transactions

Additional Journal Information:: Journal Volume: 44; Journal Issue: 25; Journal ID: ISSN 1477-9226

Publisher:: Royal Society of Chemistry

Country of Publication:: United States

Language:: English

Subject:: 36 MATERIALS SCIENCE

Citation Formats


                    Yang, Xi, Wang, Shanshan, Ghiviriga, Ion, Abboud, Khalil A., and Veige, Adam S. Organogold oligomers: Exploiting iClick and aurophilic cluster formation to prepare solution stable Au4 repeating units.  United States: N. p., 2015. 
        Web.  doi:10.1039/C5DT00282F.

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                    Yang, Xi, Wang, Shanshan, Ghiviriga, Ion, Abboud, Khalil A., & Veige, Adam S. Organogold oligomers: Exploiting iClick and aurophilic cluster formation to prepare solution stable Au4 repeating units.  United States.  https://doi.org/10.1039/C5DT00282F

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                    Yang, Xi, Wang, Shanshan, Ghiviriga, Ion, Abboud, Khalil A., and Veige, Adam S. 2015.  
        "Organogold oligomers: Exploiting iClick and aurophilic cluster formation to prepare solution stable Au4 repeating units".  United States.  https://doi.org/10.1039/C5DT00282F.  https://www.osti.gov/servlets/purl/1225601.

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@article{osti_1225601,

  title        = {Organogold oligomers: Exploiting iClick and aurophilic cluster formation to prepare solution stable Au4 repeating units},

  author       = {Yang, Xi and Wang, Shanshan and Ghiviriga, Ion and Abboud, Khalil A. and Veige, Adam S.},

  abstractNote = {A novel synthetic method to create gold based metallo–oligomers/polymers via the combination of inorganic click (iClick) with intermolecular aurophilic interactions is demonstrated. Complexes [PEt3Au]4(μ-N3C2C6H5) (1) and [PPhMe2Au]43C2C6H5) (2) and {[PEt3Au]4[(μ-N3C2)2-9,9-dihexyl-9H-fluorene]}n (8) have been synthesized via iClick. The tetranuclear structures of 1 and 2, induced by aurophilic bonding, are confirmed in the solid state through single crystal X-ray diffraction experiments and in solution via variable temperature NMR spectroscopy. The extended 1D structure of 8 is constructed by aurophilic induced self-assembly. 1H DOSY NMR analysis reveals that the aurophilic bonds in 1, 2, and 8 are retained in the solution phase. The degree of polymerization within complex 8 is temperature and concentration dependent, as determined by 1H DOSY NMR. The complex 8 is a rare example of a solution stable higher ordered structure linked by aurophilic interactions.},

  doi          = {10.1039/C5DT00282F},

  url          = {https://www.osti.gov/biblio/1225601},
  journal      = {Dalton Transactions},

  issn         = {1477-9226},

  number       = 25,

  volume       = 44,

  place        = {United States},

  year         = {Tue May 19 00:00:00 EDT 2015},

  month        = {Tue May 19 00:00:00 EDT 2015}

}

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Scheme 1: iClick reactions.

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Works referencing / citing this record:

Gold( ii ) in redox-switchable gold( i ) catalysis
journal, January 2019

Veit, Philipp; Volkert, Carla; Förster, Christoph
Chemical Communications, Vol. 55, Issue 32
https://doi.org/10.1039/c9cc00283a

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Expanding iClick to group 9 metals

Journal Article Beto, Christopher; Yang, Xi; Powers, Andrew; ... - Polyhedron

In this study, the iClick (inorganic click) reactions between gold-acetylides and group 9 transition metal-azide complexes are presented. Complexes [Rh(CO)(PPh₃)₂][PPh₃Au](μ-N₃C₂C₆H₄NO₂) (3), {[Rh(CO)(PPh₃)][PPh₃Au](μ-N₃C₂C₆H₄NO₂)}₂ (4), and [(CO)(PPh₃)₂IrAuPPh₃](μ-N₃C₂C₆H₄NO₂) (6) have been synthesized via M-azide/M-acetylide cycloaddition reactions between PPh₃Au(Ctriple bond; length of mdashCC₆H₄NO₂) (2) and either Rh(CO)(PPh₃)₂N₃ (1), or Ir(CO)(PPh₃)₂N₃ (5). Complexes 3, 4, and 6 have been characterized by a combination of NMR spectroscopies, crystallography and combustion analysis.
Cited by 12
https://doi.org/10.1016/j.poly.2015.08.032

Full Text Available
Au-iClick mirrors the mechanism of copper catalyzed azide–alkyne cycloaddition (CuAAC)

Journal Article Powers, Andrew; Ghiviriga, Ion; Abboud, Khalil; ... - Dalton Transactions

This report outlines the investigation of the iClick mechanism between gold(I)-azides and gold(I)-acetylides to yield digold triazolates. Isolation of digold triazolate complexes offer compelling support for the role of two copper(I) ions in CuAAC. In addition, a kinetic investigation reveals the reaction is first order in both Au(I)-N₃ and Au(I)-C≡C-R equivalent to C-R, thus second order overall. A Hammett plot with a ρ = 1.02(5) signifies electron-withdrawing groups accelerate the cycloaddition by facilitating the coordination of the second gold ion in a π-complex. Rate inhibition by the addition of free triphenylphosphine to the reaction indicates that ligand dissociation is amore »« less
Cited by 34
https://doi.org/10.1039/c5dt02405f

Full Text Available
Trapped Intermediate of a Meerwein–Pondorf–Verley Reduction of Hydroxy Benzaldehyde to a Dialkoxide by Titanium Alkoxides

Journal Article Boyle, Timothy; Guerrero, Fernando; Alam, Todd; ... - Inorganic Chemistry

A series of titanium alkoxides ([Ti(OR)₄] (OR = OCH(CH₃)₂ (OPri), OC(CH₃)₃ (OBut), and OCH₂C(CH₃)₃ (ONep)) were modified with a set of substituted hydroxyl-benzaldehydes [HO-BzA-Lx: x = 1, 2-hydroxybenzaldehyde (L = H), 2-hydroxy-3-methoxybenzaldehyde (OMe-3), 5-bromo-2-hydroxybenzaldehyde (Br-5), 2-hydroxy-5-nitrobenzaldehyde (NO₂-5); x = 2, 3,5-di-tert-butyl-2-hydroxybenzaldehyde (Bu^t-3,5), 2-hydroxy-3,5-diiodobenzaldehyde (I-3,5)] in pyridine (py). Instead of the expected simple substitution, each of the HO-BzA-Lx modifiers were reduced to their respective diol [(py)(OR)₂Ti(κ²(O,μ-O')(OC₆H_4–x(CH₂O)-2)(L)_x] (OR = OPrⁱ, x = 1, L = H (1a), OMe-3 (2a), Br-5 (3a·py), NO2-5 (4a·4py); x = 2, But-3,5 (5a), I-3,5 (6a), ONep; x = 1, L = H (1b), OMe-3 (2b), Br-5 (3b·py),more »« less
Cited by 2
https://doi.org/10.1021/acs.inorgchem.9b03134

Full Text Available
Fluxional behavior of {eta}{sup 1},{eta}{sup 2}-cyclooctenylpalladium acetylacetonate and related complexes

Journal Article Stockland, Jr, R; Anderson, G - Organometallics

The cyclooctenylpalladium complexes [Pd({eta}{sup 1},{eta}{sup 2}-C{sub 8}H{sub 12}{center_dot}R)(acac)] exhibit fluxional behavior in solution that equilibrates the acac methyl environments. Free energies of activation for the process have been determined by variable-temperature NMR spectroscopy. These appear to show no dependence on the nature of exo substituents, and they are higher for bulky endo groups. Lower {Delta}G{sup {double_dagger}} values are obtained in more polar solvents or with added phosphines, suggesting the operation of an associative mechanism. In contrast, the platinum complex [Pt({eta}{sup 1},{eta}{sup 2}-C{sub 8}H{sub 12}{center_dot}OMe)(acac)] is static up to 380 K, as is the C,N-bonded palladium species [Pd(C{sub 6}H{sub 4}N{double_bond}NC{sub 6}H{submore »« less
https://doi.org/10.1021/om980324k
Bonding mode variations in palladium(II) and platinum(II) azaphosphole complexes: Identification by /sup 1/H, /sup 31/P, and /sup 195/Pt (NMR of N- and P-coordination, Pt-Cl addition to P, and dimerization

Journal Article Kraaijkamp, J; Grove, D; van Koten, G; ... - Inorg. Chem.; (United States)

The 1,2,3-diazaphosphole P/double bond/C(H)C(Me)/double bond/NNMe (L/sub A/) and the 1,2,4,3-triazaphospholes P/double bond/NC(Ph)/double bond/NNMe (L/sub B/) and P/double bond/NN(Me)C(Me)/double bond/N (L/sub C/) react with the halo-bridged dimers (MX/sub 2/(PEt/sub 3/))/sub 2/ (M = Pt/sup II/, Pd/sup II/) to afford a variety of products with MX/sub 2/(PEt/sub 3/)L (L = di- or triazaphosphole) stoichiometry. With (PdCl/sub 2/(PEt/sub 3/))/sub 2/ these azaphospholes produce trans-(PdCl/sub 2/(PEt/sub 3/)L) with /sigma/-N-bonded L. From (PtBr/sub 2/(PEt/sub 3/))/sub 2/ is obtained (PtBr/sub 2/(PEt/sub 3/)L) as a mixture of the cis /sigma/-P coordination isomer with lesser amounts of the trans /sigma/-N isomer. These azaphospholes all afford different products withmore »« less
https://doi.org/10.1021/ic00288a012

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Title: Organogold oligomers: Exploiting iClick and aurophilic cluster formation to prepare solution stable Au4 repeating units

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Rigid-Rod Polymers and Model Compounds with Gold(I) Centers Bridged by Diisocyanides and Diacetylides journal, January 1996

Synthesis, structural characterization, photophysical properties and theoretical analysis of gold(i) thiolate-phosphine complexes journal, January 2011

Syntheses, Structure, and Photoluminescence Properties of the 1-Dimensional Chain Compounds [(TPA) 2 Au][Au(CN) 2 ] and (TPA)AuCl (TPA = 1,3,5-Triaza-7-phosphaadamantane) journal, December 2002

Click Chemistry: Diverse Chemical Function from a Few Good Reactions journal, June 2001

Cycloaddition reactivity studies of first-row transition metal–azide complexes and alkynes: an inorganic click reaction for metalloenzyme inhibitor synthesis journal, January 2012

Carbon−Gold Bond Formation through [3 + 2] Cycloaddition Reactions of Gold(I) Azides and Terminal Alkynes journal, January 2007

Strain‐Promoted Azide–Alkyne Cycloaddition with Ruthenium(II)–Azido Complexes journal, October 2013

Oligomerization of Au(CN) 2 - and Ag(CN) 2 - Ions in Solution via Ground-State Aurophilic and Argentophilic Bonding journal, October 2000

Metal-Assisted Cycloaddition Reactions in Organotransition Metal Chemistry journal, May 1997

Nuclearity control in gold dithiocarboxylato compounds journal, January 2010

The Structural Diversity Triggered by Intermolecular Interactions between AuIS2 Groups: Aurophilia and Beyond journal, July 2012

Cytotoxic gold(i)-bearing dendrimers from alkyne precursors journal, January 2011

Applications of gold(i) alkynyl systems: a growing field to explore journal, January 2011

The “Click” Reaction Involving Metal Azides, Metal Alkynes, or Both: An Exploration into Multimetal Structures journal, February 2013

Azide alkyne cycloaddition facilitated by hexanuclear rhenium chalcogenide cluster complexes journal, January 2013

Precious metal polymers: platinum or gold atoms in the backbone journal, January 1998

Highlights on the recent advances in gold chemistry—a photophysical perspective journal, January 2008

Luminescence Tribochromism and Bright Emission in Gold(I) Thiouracilate Complexes journal, July 2003

‘Click’ Chemistry in Polymer and Material Science: An Update journal, July 2008

A briefing on aurophilicity journal, January 2008

1,3-Dipolar cycloaddition between a metal–azide (Ph3PAuN3) and a metal–acetylide (Ph3PAuCCPh): an inorganic version of a click reaction journal, January 2011

Crystal Chemistry of the Gold (I) Trimer, Au 3 (NC 5 H 4 ) 3 : Formation of Hourglass Figures and Self-Association through Aurophilic Attraction journal, May 2002

Mono and dinuclear areneruthenium( ii ) triazoles by 1,3-dipolar cycloadditions to a coordinated azide in ruthenium( ii ) compounds journal, January 2011

Doubly and triply bridged dihapto phenylethynyl triosmium clusters by oxidative addition of phenylethynyl gold compounds. X-Ray crystal structure of [Os 3 (CCPh){Au(PMe 2 Ph)}(CO) 10 ] journal, January 1986

Molecular Aggregation of Annular Dinuclear Gold(I) Compounds Containing Bridging Diphosphine and Dithiolate Ligands journal, May 1997

Supramolecular assembly of molecular gold(I) compounds: An evaluation of the competition and complementarity between aurophilic (Au⋯Au) and conventional hydrogen bonding interactions journal, September 2014

Organotransition metal [3+2] cycloaddition reactions journal, August 2002

A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes journal, July 2002

621. Gold(I) alkynyls and their co-ordination complexes journal, January 1962

From {Au I ···Au I }-Coupled Cages to the Cage-Built 2-D {Au I ···Au I } Arrays: Au I ···Au I Bonding Interaction Driven Self-Assembly and Their Ag I Sensing and Photo-Switchable Behavior journal, July 2014

Macrocycles, catenanes, oligomers and polymers in gold chemistry journal, January 2008

Aurophilic interactions as a subject of current research: an up-date journal, January 2012

Polymer “Clicking” by CuAAC Reactions journal, July 2008

Amino acid bioconjugation via iClick reaction of an oxanorbornadiene-masked alkyne with a Mn I (bpy)(CO) 3 -coordinated azide journal, January 2014

Synthesis and Reactivity of Ruthenium Azido Complexes Containing a Hydridotris(pyrazolyl)borate Ligand and Dimerization of Terminal Alkynes in Organic and Aqueous Media journal, June 2009

Inorganic click (iClick) synthesis of heterotrinuclear PtII/AuI2 complexes journal, January 2013

Copper-Catalyzed Huisgen [3 + 2] Cycloaddition of Gold(I) Alkynyls with Benzyl Azide. Syntheses, Structures, and Optical Properties journal, November 2009

1,3-Dipolar Cycloadditions of Azides and Alkynes: A Universal Ligation Tool in Polymer and Materials Science journal, February 2007

A spontaneous gold(i)-azide alkyne cycloaddition reaction yields gold-peptide bioconjugates which overcome cisplatin resistance in a p53-mutant cancer cell line journal, January 2012

Toward Permetalated Alkyne/Azide 3 + 2 or “Click” Cycloadducts journal, July 2012

Ultrathin Gold Nanowires Can Be Obtained by Reducing Polymeric Strands of Oleylamine−AuCl Complexes Formed via Aurophilic Interaction journal, July 2008

Steric effects of phosphorus ligands in organometallic chemistry and homogeneous catalysis journal, June 1977

Binuclear gold(I) complexes with bridging diisocyanides and X-ray structures of [Au(tBuNC)(CN)], [Au2(dmb)(CN)2] and [Au2(tmb)(CN)2] (tmb=2,5-diisocyano-2,5-dimethylhexane; dmb=1,8-diisocyano-p-menthane) journal, July 1992

Diffusion of crown ethers in alcohols journal, October 1984

Tetragold(I) Complexes: Solution Isomerization and Tunable Solid-State Luminescence journal, November 2014

Organometallic complexes for nonlinear optics journal, January 2002

The Crystal and Molecular Structure of Cyano(methylisocyanide)gold(I). journal, January 1976

Luminescent gold(I) complexes for chemosensing journal, September 2011

Theoretical Chemistry of Gold journal, August 2004

Molekulare Theorie der Mikroreibung journal, September 1953

Click polymerization journal, January 2010

[3+2] Cycloadditions of Molybdenum(II) Azide Complexes with Nitriles and an Alkyne journal, October 2010

“Click polyester”: Synthesis of polyesters containing triazole units in the main chain via safe and rapid “click” chemistry and their properties journal, August 2010

A coumarin based gold( i )-alkynyl complex: a new class of supramolecular hydrogelators journal, January 2015

Direct Synthesis of 1,4-Disubstituted-5-alumino-1,2,3-triazoles: Copper-Catalyzed Cycloaddition of Organic Azides and Mixed Aluminum Acetylides journal, March 2010

New Structural Motifs in the Aggregation of Neutral Gold(I) Complexes: Structures and Luminescence from (Alkyl isocyanide)AuCN journal, May 2003

Study of the Effect of the Phosphane Bridging Chain Nature on the Structural and Photophysical Properties of a Series of Gold(I) Ethynylpyridine Complexes journal, June 2008

The use of aurophilic and other metal–metal interactions as crystal engineering design elements to increase structural dimensionality journal, January 2008

Luminescent Gold(I) Acetylides: From Model Compounds to Polymers journal, July 1997

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

Synthesis of Ruthenium Triazolato and Tetrazolato Complexes by 1,3-Dipolar Cycloadditions of Ruthenium Azido Complex with Alkynes and Alkenes and Regiospecific Alkylation of Triazolates journal, July 2003

Tetrahedral Gold(I) Clusters with Carba-closo-dodecaboranylethynido Ligands: [{12-(R3PAu)2CC-closo-1-CB11H11}2] journal, February 2011

Excited-State Interactions for [Au(CN) 2 - ] n and [Ag(CN) 2 - ] n Oligomers in Solution. Formation of Luminescent Gold−Gold Bonded Excimers and Exciplexes journal, November 2001

Click Polymerization book, August 2018

click polymerization book, April 2020

Direct Synthesis of 1,4-Disubstituted-5-alumino-1,2,3-triazoles: Copper-Catalyzed Cycloaddition of Organic Azides and Mixed Aluminum Acetylides journal, March 2010

Organometallic complexes for nonlinear optics journal, March 2003

1,3-Dipolar Cycloadditions of Azides and Alkynes: A Universal Ligation Tool in Polymer and Materials Science journal, May 2007

Organometallic complexes for nonlinear optics journal, September 2000

Theoretical Chemistry of Gold journal, November 2004

Gold( ii ) in redox-switchable gold( i ) catalysis journal, January 2019

Title: Organogold oligomers: Exploiting iClick and aurophilic cluster formation to prepare solution stable Au₄ repeating units

Rigid-Rod Polymers and Model Compounds with Gold(I) Centers Bridged by Diisocyanides and Diacetylides
journal, January 1996

Synthesis, structural characterization, photophysical properties and theoretical analysis of gold(i) thiolate-phosphine complexes
journal, January 2011

Syntheses, Structure, and Photoluminescence Properties of the 1-Dimensional Chain Compounds [(TPA) ₂ Au][Au(CN) ₂ ] and (TPA)AuCl (TPA = 1,3,5-Triaza-7-phosphaadamantane)
journal, December 2002

Click Chemistry: Diverse Chemical Function from a Few Good Reactions
journal, June 2001

Cycloaddition reactivity studies of first-row transition metal–azide complexes and alkynes: an inorganic click reaction for metalloenzyme inhibitor synthesis
journal, January 2012

Carbon−Gold Bond Formation through [3 + 2] Cycloaddition Reactions of Gold(I) Azides and Terminal Alkynes
journal, January 2007

Strain‐Promoted Azide–Alkyne Cycloaddition with Ruthenium(II)–Azido Complexes
journal, October 2013

Oligomerization of Au(CN) ₂ ^- and Ag(CN) ₂ ^- Ions in Solution via Ground-State Aurophilic and Argentophilic Bonding
journal, October 2000

Metal-Assisted Cycloaddition Reactions in Organotransition Metal Chemistry
journal, May 1997

Nuclearity control in gold dithiocarboxylato compounds
journal, January 2010

The Structural Diversity Triggered by Intermolecular Interactions between AuIS2 Groups: Aurophilia and Beyond
journal, July 2012

Cytotoxic gold(i)-bearing dendrimers from alkyne precursors
journal, January 2011

Applications of gold(i) alkynyl systems: a growing field to explore
journal, January 2011

The “Click” Reaction Involving Metal Azides, Metal Alkynes, or Both: An Exploration into Multimetal Structures
journal, February 2013

Azide alkyne cycloaddition facilitated by hexanuclear rhenium chalcogenide cluster complexes
journal, January 2013

Precious metal polymers: platinum or gold atoms in the backbone
journal, January 1998

Highlights on the recent advances in gold chemistry—a photophysical perspective
journal, January 2008

Luminescence Tribochromism and Bright Emission in Gold(I) Thiouracilate Complexes
journal, July 2003

‘Click’ Chemistry in Polymer and Material Science: An Update
journal, July 2008

A briefing on aurophilicity
journal, January 2008

1,3-Dipolar cycloaddition between a metal–azide (Ph3PAuN3) and a metal–acetylide (Ph3PAuCCPh): an inorganic version of a click reaction
journal, January 2011

Crystal Chemistry of the Gold (I) Trimer, Au ₃ (NC ₅ H ₄ ) ₃ : Formation of Hourglass Figures and Self-Association through Aurophilic Attraction
journal, May 2002

Mono and dinuclear areneruthenium( ii ) triazoles by 1,3-dipolar cycloadditions to a coordinated azide in ruthenium( ii ) compounds
journal, January 2011

Doubly and triply bridged dihapto phenylethynyl triosmium clusters by oxidative addition of phenylethynyl gold compounds. X-Ray crystal structure of [Os ₃ (CCPh){Au(PMe ₂ Ph)}(CO) ₁₀ ]
journal, January 1986

Molecular Aggregation of Annular Dinuclear Gold(I) Compounds Containing Bridging Diphosphine and Dithiolate Ligands
journal, May 1997

Supramolecular assembly of molecular gold(I) compounds: An evaluation of the competition and complementarity between aurophilic (Au⋯Au) and conventional hydrogen bonding interactions
journal, September 2014

Organotransition metal [3+2] cycloaddition reactions
journal, August 2002

A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes
journal, July 2002

621. Gold(I) alkynyls and their co-ordination complexes
journal, January 1962

From {Au ^I ···Au ^I }-Coupled Cages to the Cage-Built 2-D {Au ^I ···Au ^I } Arrays: Au ^I ···Au ^I Bonding Interaction Driven Self-Assembly and Their Ag ^I Sensing and Photo-Switchable Behavior
journal, July 2014

Macrocycles, catenanes, oligomers and polymers in gold chemistry
journal, January 2008

Aurophilic interactions as a subject of current research: an up-date
journal, January 2012

Polymer “Clicking” by CuAAC Reactions
journal, July 2008

Amino acid bioconjugation via iClick reaction of an oxanorbornadiene-masked alkyne with a Mn ^I (bpy)(CO) ₃ -coordinated azide
journal, January 2014

Synthesis and Reactivity of Ruthenium Azido Complexes Containing a Hydridotris(pyrazolyl)borate Ligand and Dimerization of Terminal Alkynes in Organic and Aqueous Media
journal, June 2009

Inorganic click (iClick) synthesis of heterotrinuclear PtII/AuI2 complexes
journal, January 2013

Copper-Catalyzed Huisgen [3 + 2] Cycloaddition of Gold(I) Alkynyls with Benzyl Azide. Syntheses, Structures, and Optical Properties
journal, November 2009

1,3-Dipolar Cycloadditions of Azides and Alkynes: A Universal Ligation Tool in Polymer and Materials Science
journal, February 2007

A spontaneous gold(i)-azide alkyne cycloaddition reaction yields gold-peptide bioconjugates which overcome cisplatin resistance in a p53-mutant cancer cell line
journal, January 2012

Toward Permetalated Alkyne/Azide 3 + 2 or “Click” Cycloadducts
journal, July 2012

Ultrathin Gold Nanowires Can Be Obtained by Reducing Polymeric Strands of Oleylamine−AuCl Complexes Formed via Aurophilic Interaction
journal, July 2008

Steric effects of phosphorus ligands in organometallic chemistry and homogeneous catalysis
journal, June 1977

Binuclear gold(I) complexes with bridging diisocyanides and X-ray structures of [Au(tBuNC)(CN)], [Au2(dmb)(CN)2] and [Au2(tmb)(CN)2] (tmb=2,5-diisocyano-2,5-dimethylhexane; dmb=1,8-diisocyano-p-menthane)
journal, July 1992

Diffusion of crown ethers in alcohols
journal, October 1984

Tetragold(I) Complexes: Solution Isomerization and Tunable Solid-State Luminescence
journal, November 2014

Organometallic complexes for nonlinear optics
journal, January 2002

The Crystal and Molecular Structure of Cyano(methylisocyanide)gold(I).
journal, January 1976

Luminescent gold(I) complexes for chemosensing
journal, September 2011

Theoretical Chemistry of Gold
journal, August 2004

Molekulare Theorie der Mikroreibung
journal, September 1953

Click polymerization
journal, January 2010

[3+2] Cycloadditions of Molybdenum(II) Azide Complexes with Nitriles and an Alkyne
journal, October 2010

“Click polyester”: Synthesis of polyesters containing triazole units in the main chain via safe and rapid “click” chemistry and their properties
journal, August 2010

A coumarin based gold( i )-alkynyl complex: a new class of supramolecular hydrogelators
journal, January 2015

Direct Synthesis of 1,4-Disubstituted-5-alumino-1,2,3-triazoles: Copper-Catalyzed Cycloaddition of Organic Azides and Mixed Aluminum Acetylides
journal, March 2010

New Structural Motifs in the Aggregation of Neutral Gold(I) Complexes: Structures and Luminescence from (Alkyl isocyanide)AuCN
journal, May 2003

Study of the Effect of the Phosphane Bridging Chain Nature on the Structural and Photophysical Properties of a Series of Gold(I) Ethynylpyridine Complexes
journal, June 2008

The use of aurophilic and other metal–metal interactions as crystal engineering design elements to increase structural dimensionality
journal, January 2008

Luminescent Gold(I) Acetylides: From Model Compounds to Polymers
journal, July 1997

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

Synthesis of Ruthenium Triazolato and Tetrazolato Complexes by 1,3-Dipolar Cycloadditions of Ruthenium Azido Complex with Alkynes and Alkenes and Regiospecific Alkylation of Triazolates
journal, July 2003

Tetrahedral Gold(I) Clusters with Carba-closo-dodecaboranylethynido Ligands: [{12-(R3PAu)2CC-closo-1-CB11H11}2]
journal, February 2011

Excited-State Interactions for [Au(CN) ₂ ^- ] _n and [Ag(CN) ₂ ^- ] _n Oligomers in Solution. Formation of Luminescent Gold−Gold Bonded Excimers and Exciplexes
journal, November 2001

Click Polymerization
book, August 2018

click polymerization
book, April 2020

Direct Synthesis of 1,4-Disubstituted-5-alumino-1,2,3-triazoles: Copper-Catalyzed Cycloaddition of Organic Azides and Mixed Aluminum Acetylides
journal, March 2010

Organometallic complexes for nonlinear optics
journal, March 2003

1,3-Dipolar Cycloadditions of Azides and Alkynes: A Universal Ligation Tool in Polymer and Materials Science
journal, May 2007

Organometallic complexes for nonlinear optics
journal, September 2000

Theoretical Chemistry of Gold
journal, November 2004

Gold( ii ) in redox-switchable gold( i ) catalysis
journal, January 2019