Mechanical vs Electronic Strain: Oval-Shaped Alkynyl-Pt(II)-Phosphine Macrocycles

Plutnar, Jan; Givelet, Cecile; Lemouchi, Cyprien; Jaklová Dytrtová, Jana; Císařová, Ivana; Teat, Simon J.; Michl, Josef

doi:10.1021/acs.organomet.9b00633

Title: Mechanical vs Electronic Strain: Oval-Shaped Alkynyl-Pt(II)-Phosphine Macrocycles

Abstract

Pyridine-terminated molecular rods and either (i) the cis-(dppp)(I)Pt(C≡C-triptycene-C≡C)Pt(I)(dppp) rod or (ii) the trans-(PEt₃)₂(I)Pt(C≡C-biphenyl-C≡C)Pt(I)(PEt₃)₂ rod assemble into macrocycles, characterized by NMR, ESI-IMS, and in two cases also single-crystal X-ray diffraction. The former form rectangles with bidentate phosphine-containing cis-coordinated Pt(II)-alkyne corners. In the latter, the preference of the Pt centers for a trans configuration overrules the preference of the triple bonds for linearity and NMR shows that they have oval structures with alternating bent rod and bent trans (C≡C)Pt(PEt₃)₂(C≡C) components, in agreement with density functional theory calculations.

Authors:

Plutnar, Jan ^[1]; Givelet, Cecile ^[2];

^[2]; Jaklová Dytrtová, Jana ^[3]; Císařová, Ivana ^[4]; Teat, Simon J. ^[5];

^[2]

Czech Academy of Sciences, Prague (Czech Republic). Inst. of Organic Chemistry and Biochemistry
Czech Academy of Sciences, Prague (Czech Republic). Inst. of Organic Chemistry and Biochemistry; Univ. of Colorado, Boulder, CO (United States)
Czech Academy of Sciences, Prague (Czech Republic). Inst. of Organic Chemistry and Biochemistry; Charles Univ., Prague (Czech Republic). Faculty of Mathematics and Physics
Charles Univ., Prague (Czech Republic). Faculty of Mathematics and Physics
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Advanced Light Source (ALS)

Publication Date:: 2019-12-02

Research Org.:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF); European Research Council (ERC)

OSTI Identifier:: 1580421

Grant/Contract Number:: AC02-05CH11231; 227756

Resource Type:: Accepted Manuscript

Journal Name:: Organometallics

Additional Journal Information:: Journal Volume: 38; Journal Issue: 24; Journal ID: ISSN 0276-7333

Publisher:: American Chemical Society

Country of Publication:: United States

Language:: English

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

Citation Formats


                    Plutnar, Jan, Givelet, Cecile, Lemouchi, Cyprien, Jaklová Dytrtová, Jana, Císařová, Ivana, Teat, Simon J., and Michl, Josef. Mechanical vs Electronic Strain: Oval-Shaped Alkynyl-Pt(II)-Phosphine Macrocycles.  United States: N. p., 2019. 
Web.  doi:10.1021/acs.organomet.9b00633.

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                    Plutnar, Jan, Givelet, Cecile, Lemouchi, Cyprien, Jaklová Dytrtová, Jana, Císařová, Ivana, Teat, Simon J., & Michl, Josef. Mechanical vs Electronic Strain: Oval-Shaped Alkynyl-Pt(II)-Phosphine Macrocycles.  United States.  https://doi.org/10.1021/acs.organomet.9b00633

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                    Plutnar, Jan, Givelet, Cecile, Lemouchi, Cyprien, Jaklová Dytrtová, Jana, Císařová, Ivana, Teat, Simon J., and Michl, Josef. Mon .  
"Mechanical vs Electronic Strain: Oval-Shaped Alkynyl-Pt(II)-Phosphine Macrocycles".  United States.  https://doi.org/10.1021/acs.organomet.9b00633.  https://www.osti.gov/servlets/purl/1580421.

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@article{osti_1580421,

  title        = {Mechanical vs Electronic Strain: Oval-Shaped Alkynyl-Pt(II)-Phosphine Macrocycles},

  author       = {Plutnar, Jan and Givelet, Cecile and Lemouchi, Cyprien and Jaklová Dytrtová, Jana and Císařová, Ivana and Teat, Simon J. and Michl, Josef},

  abstractNote = {Pyridine-terminated molecular rods and either (i) the cis-(dppp)(I)Pt(C≡C-triptycene-C≡C)Pt(I)(dppp) rod or (ii) the trans-(PEt3)2(I)Pt(C≡C-biphenyl-C≡C)Pt(I)(PEt3)2 rod assemble into macrocycles, characterized by NMR, ESI-IMS, and in two cases also single-crystal X-ray diffraction. The former form rectangles with bidentate phosphine-containing cis-coordinated Pt(II)-alkyne corners. In the latter, the preference of the Pt centers for a trans configuration overrules the preference of the triple bonds for linearity and NMR shows that they have oval structures with alternating bent rod and bent trans (C≡C)Pt(PEt3)2(C≡C) components, in agreement with density functional theory calculations.},

  doi          = {10.1021/acs.organomet.9b00633},

  journal      = {Organometallics},

  number       = 24,

  volume       = 38,

  place        = {United States},

  year         = {2019},

  month        = {12}

}

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https://doi.org/10.1021/acs.organomet.9b00633

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Title: Mechanical vs Electronic Strain: Oval-Shaped Alkynyl-Pt(II)-Phosphine Macrocycles

Abstract

Citation Formats

Novel preparation of σ-alkynyl complexes of transition metals by copper( I ) iodide-catalysed dehydrohalogenation journal, January 1977

Syntheses and properties of cis- and trans-dialkynyl complexes of platinum(II) journal, January 1978

Coordination-Driven Assembly of Molecular Rectangles via an Organometallic “Clip” journal, November 2000

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Synthesis of a Bis(pyridyl)-Substituted Perylene Diimide Ligand and Incorporation into a Supramolecular Rhomboid and Rectangle via Coordination Driven Self-Assembly journal, February 2005

A Self-Assembled Supramolecular Optical Sensor for Ni(II), Cd(II), and Cr(III) journal, March 2004

Facile Self-Assembly of Predesigned Neutral 2D Pt-Macrocycles via a New Class of Rigid Oxygen Donor Linkers journal, November 2003

Self-Assembly of Heterobimetallic Neutral Macrocycles Incorporating Ferrocene Spacer Groups: Spectroelectrochemical Analysis of the Double Two-Electron Oxidation of a Molecular Rectangle journal, August 2005

Synthesis and Structural Characterization of Carborane-Containing Neutral, Self-Assembled Pt-Metallacycles journal, December 2005

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Synthesis and Spectroscopic and Electronic Characterization of New Cis-Configured Di- to Multiplatinum Alkynyls journal, May 2006

Using ligand exchange reactions to control the coordination environment of Pt(II) acetylide complexes: applications to conjugated metallacyclynes journal, October 2003

A Simple, One-Step Procedure for the Formation of Chiral Metallamacrocycles journal, November 2004

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Self-Assembled Trigonal Prismatic Altitudinal Rotors with Triptycene Paddle Wheels journal, January 2005

Synthesis of Single-Crystal Tetra(4-pyridyl)porphyrin Rectangular Nanotubes in the Vapor Phase journal, March 2009

Copper(I) Alkyne and Alkynide Complexes journal, August 2012

Syntheses, optical and electrochemical properties of 4,4′-bis-[2-(3,4-dibutyl-2-thienylethynyl)]biphenyl and its oligomers journal, April 2005

Octatetrayne-linked porphyrins: ‘stretched’ cyclic dimers and trimers with very spacious cavities journal, January 1995

Consecutive One-Pot Sonogashira-Glaser Coupling Sequence - Direct Preparation of Symmetrical Diynes by Sequential Pd/Cu Catalysis journal, December 2010

Improved syntheses of [PtMe2(1,5-COD)] journal, November 1986

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SHELXT – Integrated space-group and crystal-structure determination journal, January 2015

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An empirical correction for absorption anisotropy journal, January 1995

Corrections to tabulated anomalous-scattering factors journal, March 1990

WinGX suite for small-molecule single-crystal crystallography journal, August 1999

Novel preparation of σ-alkynyl complexes of transition metals by copper( I ) iodide-catalysed dehydrohalogenation
journal, January 1977

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journal, January 1978

Coordination-Driven Assembly of Molecular Rectangles via an Organometallic “Clip”
journal, November 2000

Metalla-Supramolecular Rectangles as Electron Reservoirs for Multielectron Reduction and Oxidation
journal, July 2002

Size Selective Self-Sorting in Coordination-Driven Self-Assembly of Finite Ensembles
journal, April 2008

Direct and Quantitative Characterization of Dynamic Ligand Exchange between Coordination-Driven Self-Assembled Supramolecular Polygons
journal, February 2009

X-ray Diffraction and DOSY NMR Characterization of Self-Assembled Supramolecular Metallocyclic Species in Solution
journal, August 2005

Synthesis of a Bis(pyridyl)-Substituted Perylene Diimide Ligand and Incorporation into a Supramolecular Rhomboid and Rectangle via Coordination Driven Self-Assembly
journal, February 2005

A Self-Assembled Supramolecular Optical Sensor for Ni(II), Cd(II), and Cr(III)
journal, March 2004

Facile Self-Assembly of Predesigned Neutral 2D Pt-Macrocycles via a New Class of Rigid Oxygen Donor Linkers
journal, November 2003

Self-Assembly of Heterobimetallic Neutral Macrocycles Incorporating Ferrocene Spacer Groups: Spectroelectrochemical Analysis of the Double Two-Electron Oxidation of a Molecular Rectangle
journal, August 2005

Synthesis and Structural Characterization of Carborane-Containing Neutral, Self-Assembled Pt-Metallacycles
journal, December 2005

Facile Synthesis of Enantiopure Chiral Molecular Rectangles Exhibiting Induced Circular Dichroism
journal, March 2006

Self-Assembly of Neutral Platinum-Based Supramolecular Ensembles Incorporating Oxocarbon Dianions and Oxalate
journal, October 2005

Self-Assembly of Metallamacrocycles Using a Dinuclear Organometallic Acceptor: Synthesis, Characterization, and Sensing Study
journal, November 2011

Covalent Stabilization: A Sturdy Molecular Square from Reversible Metal-Ion-Directed Self-Assembly
journal, December 2011

Directed assembly of chiral organometallic squares that exhibit dual luminescenceElectronic supplementary information (ESI) available: experimental procedures and nine figures. See http://www.rsc.org/suppdata/cc/b3/b307727f/
journal, January 2003

Synthesis of Neutral Molecular Squares Composed of Bis(phosphine)platinum Corner Units and Dialkynyl Linkers. Solid-State Characterization of [Pt(μ-C⋮CC⋮C)(dppp)] ₄
journal, September 2004

Synthesis and Spectroscopic and Electronic Characterization of New Cis-Configured Di- to Multiplatinum Alkynyls
journal, May 2006

Using ligand exchange reactions to control the coordination environment of Pt(II) acetylide complexes: applications to conjugated metallacyclynes
journal, October 2003

A Simple, One-Step Procedure for the Formation of Chiral Metallamacrocycles
journal, November 2004

Coordination-Driven Self-Assembly of M ₃ L ₂ Trigonal Cages from Preorganized Metalloligands Incorporating Octahedral Metal Centers and Fluorescent Detection of Nitroaromatics
journal, February 2011

Self-Assembled Trigonal Prismatic Altitudinal Rotors with Triptycene Paddle Wheels
journal, January 2005

Synthesis of Single-Crystal Tetra(4-pyridyl)porphyrin Rectangular Nanotubes in the Vapor Phase
journal, March 2009

Copper(I) Alkyne and Alkynide Complexes
journal, August 2012

Syntheses, optical and electrochemical properties of 4,4′-bis-[2-(3,4-dibutyl-2-thienylethynyl)]biphenyl and its oligomers
journal, April 2005

Octatetrayne-linked porphyrins: ‘stretched’ cyclic dimers and trimers with very spacious cavities
journal, January 1995

Consecutive One-Pot Sonogashira-Glaser Coupling Sequence - Direct Preparation of Symmetrical Diynes by Sequential Pd/Cu Catalysis
journal, December 2010

Improved syntheses of [PtMe2(1,5-COD)]
journal, November 1986

Synthesis and Electronic Properties of Conjugated Pentacene Dimers
journal, September 2008

SHELXT – Integrated space-group and crystal-structure determination
journal, January 2015

Crystal structure refinement with SHELXL
journal, January 2015

Structure validation in chemical crystallography
journal, January 2009

An empirical correction for absorption anisotropy
journal, January 1995

Corrections to tabulated anomalous-scattering factors
journal, March 1990

WinGX suite for small-molecule single-crystal crystallography
journal, August 1999