Programmed twisting of phenylene–ethynylene linkages from aromatic stacking interactions

Mullin, William J.; Pawle, Robert H.; Sharber, Seth A.; Müller, Peter; Thomas, Samuel W.

doi:10.1039/c8tc05612a

Title: Programmed twisting of phenylene–ethynylene linkages from aromatic stacking interactions

Abstract

Control over the conformation and packing of conjugated materials is an unsolved problem that prevents the rational design of organic optoelectronics, such as preventing self-quenching of luminescent molecules. Exacerbating this challenge is a general lack of widely applicable strategies for controlling packing with discrete, directional non-covalent interactions. Here, we present a series of conjugated molecules with diverse backbones of three or four arenes that feature pentafluorobenzyl ester substituents. Nearly all the compounds reveal intramolecular stacking interactions between the fluoroarene (ArF) side-chains and non-fluorinated arenes (ArH) in the middle of the chromophores; a twisted PE linkage accompanies each example of this intramolecular ArF–ArH stacking. Furthermore, these molecules can resist dramatic changes to emission upon transition from organic solution to thin film when ArF rings prevent interchromophore interactions. By broadening the structural space of conjugated backbones over which ArF–ArH stacking can twist PE linkages reliably and prevent self-quenching of solids with simple synthetic approaches, this work suggests fluorinated benzyl ester substituents adjacent to phenylene ethynylene linkages as supramolecular synthons for the crystal engineering of organic optoelectronic materials.

Authors:

Mullin, William J. ^[1]; Pawle, Robert H. ^[1]; Sharber, Seth A. ^[1]; Müller, Peter ^[2];

^[1]

Tufts Univ., Medford, MA (United States). Dept. of Chemistry
Massachusetts Inst. of Technology (MIT), Cambridge, MA (United States). Dept. of Chemistry

Publication Date:: Tue Dec 18 00:00:00 EST 2018

Research Org.:: Tufts Univ., Medford, MA (United States)

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

OSTI Identifier:: 1612546

Alternate Identifier(s):: OSTI ID: 1490553

Grant/Contract Number:: SC0016423

Resource Type:: Accepted Manuscript

Journal Name:: Journal of Materials Chemistry C

Additional Journal Information:: Journal Volume: 7; Journal Issue: 5; Journal ID: ISSN 2050-7526

Publisher:: Royal Society of Chemistry

Country of Publication:: United States

Language:: English

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

Citation Formats


                    Mullin, William J., Pawle, Robert H., Sharber, Seth A., Müller, Peter, and Thomas, Samuel W. Programmed twisting of phenylene–ethynylene linkages from aromatic stacking interactions.  United States: N. p., 2018. 
Web.  doi:10.1039/c8tc05612a.

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                    Mullin, William J., Pawle, Robert H., Sharber, Seth A., Müller, Peter, & Thomas, Samuel W. Programmed twisting of phenylene–ethynylene linkages from aromatic stacking interactions.  United States.  https://doi.org/10.1039/c8tc05612a

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                    Mullin, William J., Pawle, Robert H., Sharber, Seth A., Müller, Peter, and Thomas, Samuel W. Tue .  
"Programmed twisting of phenylene–ethynylene linkages from aromatic stacking interactions".  United States.  https://doi.org/10.1039/c8tc05612a.  https://www.osti.gov/servlets/purl/1612546.

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@article{osti_1612546,

  title        = {Programmed twisting of phenylene–ethynylene linkages from aromatic stacking interactions},

  author       = {Mullin, William J. and Pawle, Robert H. and Sharber, Seth A. and Müller, Peter and Thomas, Samuel W.},

  abstractNote = {Control over the conformation and packing of conjugated materials is an unsolved problem that prevents the rational design of organic optoelectronics, such as preventing self-quenching of luminescent molecules. Exacerbating this challenge is a general lack of widely applicable strategies for controlling packing with discrete, directional non-covalent interactions. Here, we present a series of conjugated molecules with diverse backbones of three or four arenes that feature pentafluorobenzyl ester substituents. Nearly all the compounds reveal intramolecular stacking interactions between the fluoroarene (ArF) side-chains and non-fluorinated arenes (ArH) in the middle of the chromophores; a twisted PE linkage accompanies each example of this intramolecular ArF–ArH stacking. Furthermore, these molecules can resist dramatic changes to emission upon transition from organic solution to thin film when ArF rings prevent interchromophore interactions. By broadening the structural space of conjugated backbones over which ArF–ArH stacking can twist PE linkages reliably and prevent self-quenching of solids with simple synthetic approaches, this work suggests fluorinated benzyl ester substituents adjacent to phenylene ethynylene linkages as supramolecular synthons for the crystal engineering of organic optoelectronic materials.},

  doi          = {10.1039/c8tc05612a},

  journal      = {Journal of Materials Chemistry C},

  number       = 5,

  volume       = 7,

  place        = {United States},

  year         = {Tue Dec 18 00:00:00 EST 2018},

  month        = {Tue Dec 18 00:00:00 EST 2018}

}

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https://doi.org/10.1039/c8tc05612a

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Title: Programmed twisting of phenylene–ethynylene linkages from aromatic stacking interactions

Abstract

Citation Formats

Big macrocyclic assemblies of carboranes (big MACs): synthesis and crystal structure of a macrocyclic assembly of four carboranes containing alternate ortho- and meta-carborane icosahedra linked by para-phenylene units journal, August 2003

Electrochemically assisted mechanically controllable break junction studies on the stacking configurations of oligo(phenylene ethynylene)s molecular junctions journal, May 2016

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Anthracene Based Conjugated Polymers: Correlation between π−π-Stacking Ability, Photophysical Properties, Charge Carrier Mobility, and Photovoltaic Performance journal, February 2010

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Conjugated Polyelectrolytes: Synthesis, Photophysics, and Applications journal, June 2009

Synergy between experimental and computational studies of aromatic stacking interactions journal, January 2017

Substituent Effects That Control Conjugated Oligomer Conformation through Non-covalent Interactions journal, March 2017

Theoretical Interpretation of Conductivity Measurements of a Thiotolane Sandwich. A Molecular Scale Electronic Controller journal, April 1998

Perfluorinated and Half-Fluorinated Rubrenes: Synthesis and Crystal Packing Arrangements journal, July 2017

Phenyl/Pentafluorophenyl Interactions and the Generation of Ordered Mixed Crystals:sym-Triphenethynylbenzene andsym-Tris(perfluorophenethynyl)benzene journal, July 2000

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Perfluoropentacene: High-Performance p−n Junctions and Complementary Circuits with Pentacene journal, July 2004

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Light-Induced Antibacterial Activity of Symmetrical and Asymmetrical Oligophenylene Ethynylenes journal, April 2011

Solid-State Packing of Conjugated Oligomers: From π-Stacks to the Herringbone Structure journal, April 2004

Replacing Phenyl Ring with Thiophene: An Approach to Longer Wavelength Aza-dipyrromethene Boron Difluoride (Aza-BODIPY) Dyes journal, December 2011

From Tunneling to Hopping: A Comprehensive Investigation of Charge Transport Mechanism in Molecular Junctions Based on Oligo( p -phenylene ethynylene)s journal, November 2009

Role of Molecular Packing in Determining Solid-State Optical Properties of π-Conjugated Materials journal, March 2011

Programmed Synthesis of Molecular Wires with Fixed Insulation and Defined Length Based on Oligo(phenylene ethynylene) and Permethylated α-Cyclodextrins journal, July 2017

Structure of the Lowest Temperature Phase of the Solid Benzene–Hexafluorobenzene Adduct journal, December 1992

Sugar-Poly(para-phenylene ethynylene) Conjugates as Sensory Materials: Efficient Quenching by Hg2+ and Pb2+ Ions journal, December 2004

Turn-on fluorescent sensor for the detection of cyanide based on a novel dicyanovinyl phenylacetylene journal, January 2017

Self-Sterilizing, Self-Cleaning Mixed Polymeric Multifunctional Antimicrobial Surfaces journal, December 2015

Conformational and Electronic Engineering of Twisted Diphenylacetylenes journal, September 2003

Phenyl/Pentafluorophenyl Interactions and the Generation of Ordered Mixed Crystals:sym-Triphenethynylbenzene andsym-Tris(perfluorophenethynyl)benzene journal, July 2000

Building Blocks for n-Type Organic Electronics: Regiochemically Modulated Inversion of Majority Carrier Sign in Perfluoroarene-Modified Polythiophene Semiconductors journal, August 2003

Interactions with Aromatic Rings in Chemical and Biological Recognition. journal, June 2003

Big macrocyclic assemblies of carboranes (big MACs): synthesis and crystal structure of a macrocyclic assembly of four carboranes containing alternate ortho- and meta-carborane icosahedra linked by para-phenylene units
journal, August 2003

Electrochemically assisted mechanically controllable break junction studies on the stacking configurations of oligo(phenylene ethynylene)s molecular junctions
journal, May 2016

Fluorocarbon-Modified Organic Semiconductors: Molecular Architecture, Electronic, and Crystal Structure Tuning of Arene- versus Fluoroarene-Thiophene Oligomer Thin-Film Properties
journal, May 2006

Anthracene Based Conjugated Polymers: Correlation between π−π-Stacking Ability, Photophysical Properties, Charge Carrier Mobility, and Photovoltaic Performance
journal, February 2010

Effect of Varying Thiophene Units on Charge-Transport and Photovoltaic Properties of Poly(phenylene ethynylene)- alt -poly(phenylene vinylene) Polymers
journal, June 2014

Reversible mechanofluorochromism of aniline-terminated phenylene ethynylenes
journal, January 2018

Partial Fluorination Overcomes Herringbone Crystal Packing in Small Polycyclic Aromatics ^†
journal, March 2005

Conjugated Polyelectrolytes: Synthesis, Photophysics, and Applications
journal, June 2009

Synergy between experimental and computational studies of aromatic stacking interactions
journal, January 2017

Substituent Effects That Control Conjugated Oligomer Conformation through Non-covalent Interactions
journal, March 2017

Theoretical Interpretation of Conductivity Measurements of a Thiotolane Sandwich. A Molecular Scale Electronic Controller
journal, April 1998

Perfluorinated and Half-Fluorinated Rubrenes: Synthesis and Crystal Packing Arrangements
journal, July 2017

Phenyl/Pentafluorophenyl Interactions and the Generation of Ordered Mixed Crystals:sym-Triphenethynylbenzene andsym-Tris(perfluorophenethynyl)benzene
journal, July 2000

Photovoltaic Cells Based on Sequentially Adsorbed Multilayers of Conjugated Poly( p -phenylene ethynylene)s and a Water-Soluble Fullerene Derivative ^†
journal, October 2005

Twisting and piezochromism of phenylene-ethynylenes with aromatic interactions between side chains and main chains
journal, January 2014

Twisted Tethered Tolanes: Unanticipated Long-Lived Phosphorescence at 77 K
journal, January 2013

Building upon Supramolecular Synthons: Some Aspects of Crystal Engineering
journal, May 2015

Perfluorophenyl-Phenyl Interactions in the Crystallization and Topochemical Polymerization of Triacetylene Monomers
journal, September 2009

Building Blocks for n-Type Organic Electronics: Regiochemically Modulated Inversion of Majority Carrier Sign in Perfluoroarene-Modified Polythiophene Semiconductors
journal, August 2003

Gold-catalyzed C–S bond formation from thiols
journal, January 2010

Electronic spectra of tolan in a supersonic free jet: large-amplitude torsional motion
journal, April 1984

Perfluoropentacene: High-Performance p−n Junctions and Complementary Circuits with Pentacene
journal, July 2004

Oligo( p -phenyleneethynylene)s with Hydrogen-Bonded Coplanar Conformation
journal, July 2008

Probing the Intrachain and Interchain Effects on the Fluorescence Behavior of Pentiptycene-Derived Oligo( p -phenyleneethynylene)s
journal, November 2006

Interactions with Aromatic Rings in Chemical and Biological Recognition
journal, March 2003

Organic Optoelectronic Materials: Mechanisms and Applications
journal, October 2016

QUANTUM EFFICIENCIES OF FLUORESCENCE OF ORGANIC SUBSTANCES: EFFECT OF SOLVENT AND CONCENTRATION OF THE FLUORESCENT SOLUTE ¹
journal, February 1961

Engineering a twist in 9,10-diethynylanthracenes by steric interactions
journal, January 2007

When Worlds Collide: Interactions at the Interface between Biological Systems and Synthetic Cationic Conjugated Polyelectrolytes and Oligomers
journal, June 2013

Synthesis of Rotationally Restricted and Modular Biphenyl Building Blocks
journal, November 2009

Strategies to create hierarchical self-assembled structures via cooperative non-covalent interactions
journal, January 2015

Light-Induced Antibacterial Activity of Symmetrical and Asymmetrical Oligophenylene Ethynylenes
journal, April 2011

Solid-State Packing of Conjugated Oligomers: From π-Stacks to the Herringbone Structure
journal, April 2004

Replacing Phenyl Ring with Thiophene: An Approach to Longer Wavelength Aza-dipyrromethene Boron Difluoride (Aza-BODIPY) Dyes
journal, December 2011

From Tunneling to Hopping: A Comprehensive Investigation of Charge Transport Mechanism in Molecular Junctions Based on Oligo( p -phenylene ethynylene)s
journal, November 2009

Role of Molecular Packing in Determining Solid-State Optical Properties of π-Conjugated Materials
journal, March 2011

Programmed Synthesis of Molecular Wires with Fixed Insulation and Defined Length Based on Oligo(phenylene ethynylene) and Permethylated α-Cyclodextrins
journal, July 2017

Structure of the Lowest Temperature Phase of the Solid Benzene–Hexafluorobenzene Adduct
journal, December 1992

Sugar-Poly(para-phenylene ethynylene) Conjugates as Sensory Materials: Efficient Quenching by Hg2+ and Pb2+ Ions
journal, December 2004

Turn-on fluorescent sensor for the detection of cyanide based on a novel dicyanovinyl phenylacetylene
journal, January 2017

Self-Sterilizing, Self-Cleaning Mixed Polymeric Multifunctional Antimicrobial Surfaces
journal, December 2015

Conformational and Electronic Engineering of Twisted Diphenylacetylenes
journal, September 2003

Phenyl/Pentafluorophenyl Interactions and the Generation of Ordered Mixed Crystals:sym-Triphenethynylbenzene andsym-Tris(perfluorophenethynyl)benzene
journal, July 2000

Building Blocks for n-Type Organic Electronics: Regiochemically Modulated Inversion of Majority Carrier Sign in Perfluoroarene-Modified Polythiophene Semiconductors
journal, August 2003

Interactions with Aromatic Rings in Chemical and Biological Recognition.
journal, June 2003