Skip to main content
U.S. Department of Energy
Office of Scientific and Technical Information

Bridging the Void: Halogen Bonding and Aromatic Interactions to Program Luminescence and Electronic Properties of π-Conjugated Materials in the Solid State

Journal Article · · Chemistry of Materials
 [1];  [2];  [2]
  1. Department of Chemistry, Tufts University, Medford, Massachusetts 02155, United States; Aramco Services Company, Aramco Research Center, Boston, Massachusetts 02139, United States
  2. Department of Chemistry, Tufts University, Medford, Massachusetts 02155, United States

Not provided.

Research Organization:
Tufts Univ., Medford, MA (United States)
Sponsoring Organization:
USDOE Office of Science (SC)
DOE Contract Number:
SC0016423
OSTI ID:
1852235
Journal Information:
Chemistry of Materials, Vol. 33, Issue 17; ISSN 0897-4756
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English

References (204)

Organic crystalline materials in flexible electronics journal January 2019
Low Band Gap Polymers for Roll-to-Roll Coated Polymer Solar Cells journal October 2010
All-Polymer Solar Cells: Recent Progress, Challenges, and Prospects journal February 2019
Polymer Chemistries Underpinning Materials for Skin-Inspired Electronics journal May 2019
Self-Assembled Extended π-Systems for Sensing and Security Applications journal February 2020
Conjugated Amplifying Polymers for Optical Sensing Applications journal May 2013
Designing π-conjugated polymers for organic electronics journal December 2013
25th Anniversary Article: Organic Field-Effect Transistors: The Path Beyond Amorphous Silicon journal January 2014
Thermally Activated Delayed Fluorescence Materials Towards the Breakthrough of Organoelectronics journal September 2014
Organic Electronic Materials: Recent Advances in the DFT Description of the Ground and Excited States Using Tuned Range-Separated Hybrid Functionals journal April 2014
Design strategies for organic semiconductors beyond the molecular formula journal August 2012
Role of Molecular Packing in Determining Solid-State Optical Properties of π-Conjugated Materials journal March 2011
Interchain Interactions in Organic π-Conjugated Materials: Impact on Electronic Structure, Optical Response, and Charge Transport journal July 2001
Crystal Engineering: From Molecule to Crystal journal June 2013
Role of Polymorphism and Thin-Film Morphology in Organic Semiconductors Processed by Solution Shearing journal February 2018
Conformation-Controlled Electron Transport in Single-Molecule Junctions Containing Oligo(phenylene ethynylene) Derivatives journal May 2013
Closely Stacked Oligo(phenylene ethynylene)s: Effect of π-Stacking on the Electronic Properties of Conjugated Chromophores journal April 2012
From Molecules to Interactions to Crystal Engineering: Mechanical Properties of Organic Solids journal October 2018
Crystal Engineering: A Holistic View journal November 2007
Building upon Supramolecular Synthons: Some Aspects of Crystal Engineering journal May 2015
Non-covalent routes to tune the optical properties of molecular materials journal January 2014
Molecular conformation and packing: their critical roles in the emission performance of mechanochromic fluorescence materials journal January 2017
Halogen bonding in room-temperature phosphorescent materials journal February 2020
Metal free room temperature phosphorescence from molecular self-interactions in the solid state journal January 2018
The role of hydrogen bonding in bulk-heterojunction (BHJ) solar cells: A review journal August 2018
Effective structural modification of traditional fluorophores to obtain organic mechanofluorochromic molecules journal January 2018
Developing the structure–property relationship to design solid state multi-stimuli responsive materials and their potential applications in different fields journal January 2018
Organic and Polymeric Semiconductors Enhanced by Noncovalent Conformational Locks journal July 2017
Optimizing the self‐assembly of conjugated polymers and small molecules through structurally programmed non‐covalent control journal July 2021
Hydrogen-bonding versus π–π stacking in the design of organic semiconductors: From dyes to oligomers journal April 2015
Hydrogen-bonds in molecular solids – from biological systems to organic electronics journal January 2013
Room-temperature phosphorescence-to-phosphorescence mechanochromism of a metal-free organic 1,2-diketone journal January 2019
Chalcogen bonding in materials chemistry journal November 2020
Solution Processable Pseudo n -Thienoacenes via Intramolecular S···S Lock for High Performance Organic Field Effect Transistors journal January 2020
Losing control? “Design” of crystalline organic and metal–organic networks using conformationally flexible building blocks journal January 2011
Are Halogen Bonded Structures Electrostatically Driven? journal April 2013
Halogen Bonds in Crystal Engineering: Like Hydrogen Bonds yet Different journal May 2014
σ-Hole Bond vs π-Hole Bond: A Comparison Based on Halogen Bond journal February 2016
Halogen Bonding beyond Crystals in Materials Science journal September 2019
Stability and utility of pyridyl disulfide functionality in RAFT and conventional radical polymerizations journal September 2008
Halogen bonding in polymer science: from crystal engineering to functional supramolecular polymers and materials journal January 2015
Halogen Bonding: Where We Are and Where We Are Going journal November 2012
Enhanced Room‐Temperature Phosphorescence through Intermolecular Halogen/Hydrogen Bonding journal November 2018
Halogen Bonding: A Halogen-Centered Noncovalent Interaction Yet to Be Understood journal March 2019
The Origin of Chalcogen-Bonding Interactions journal October 2017
Activating efficient phosphorescence from purely organic materials by crystal design journal February 2011
Organic Nanocrystals with Bright Red Persistent Room-Temperature Phosphorescence for Biological Applications journal August 2017
Does Halogen Bonding Promote Intersystem Crossing and Phosphorescence in Benzaldehyde? journal May 2018
Halogen Bonding Facilitates Intersystem Crossing in Iodo-BODIPY Chromophores journal January 2020
Enhancing Ultralong Organic Phosphorescence by Effective π-Type Halogen Bonding journal January 2018
Boosting the Quantum Efficiency of Ultralong Organic Phosphorescence up to 52 % via Intramolecular Halogen Bonding journal August 2020
Bright persistent luminescence from pure organic molecules through a moderate intermolecular heavy atom effect journal January 2017
Two-dimensional bricklayer arrangements of tolans using halogen bonding interactions journal January 2015
Enhancing charge mobilities in self-assembled N⋯I halogen bonded organic semiconductors: A design approach based on experimental and computational perspectives journal April 2020
Elucidating the Effects of Fluoro and Nitro Substituents on Halogen Bond Driven Assemblies of Pyridyl-Capped π-Conjugated Molecules journal October 2016
Geometric Shape Regulation and Noncovalent Synthesis of One-Dimensional Organic Luminescent Nano-/Micro-Materials journal July 2017
Anomalous Halogen–Halogen Interaction Assists Radial Chromophoric Assembly journal February 2019
Halogen–Halogen Bonded Donor-Acceptor Stacks Foster Orthogonal Electron and Hole Transport journal October 2020
Halogen-Bonded Cocrystals as Optical Materials: Next-Generation Control over Light–Matter Interactions journal January 2018
Two-Dimensional Arrangements of Bis(haloethynyl)benzenes Combining Halogen and Hydrogen Interactions journal November 2017
Mechanochemistry for Organic Chemists: An Update: Mechanochemistry for Organic Chemists: An Update journal November 2017
Facts and fictions about polymorphism journal January 2015
A Cocrystal Strategy to Tune the Luminescent Properties of Stilbene-Type Organic Solid-State Materials journal November 2011
Insight from Molecular Packing: Charge Transfer and Emission Modulation through Cocrystal Strategies journal July 2020
The Effect of Cyano Substitution on the Fluorescence Behavior of 1,2-Bis(pyridylphenyl)ethene journal April 2014
Tuning the structural and spectroscopic properties of donor–acceptor–donor oligomers via mutual X-bonding, H-bonding, and π–π interactions journal January 2018
Tuning the solid-state emission by co-crystallization through σ- and π-hole directed intermolecular interactions journal January 2019
Intrinsic and Extrinsic Heavy‐Atom Effects on the Multifaceted Emissive Behavior of Cyclic Triimidazole journal January 2019
Ultralong Organic Phosphorescence in the Solid State: The Case of Triphenylene Cocrystals with Halo- and Dihalo-penta/tetrafluorobenzene journal November 2018
Controlling Dichroism of Molecular Crystals by Cocrystallization journal January 2016
Impact of Hydrogen and Halogen Bonding Interactions on the Packing and Ionicity of Charge-Transfer Cocrystals journal December 2016
Quantum ferroelectricity in charge-transfer complex crystals journal June 2015
Rational Design of Charge-Transfer Interactions in Halogen-Bonded Co-crystals toward Versatile Solid-State Optoelectronics journal August 2015
Tailoring the Energy Levels and Cavity Structures toward Organic Cocrystal Microlasers journal November 2018
Organic σ‐Hole Containing Crystals with Enhanced Nonlinear Optical Response and Efficient Optical‐to‐THz Frequency Conversion journal January 2020
Mechanoresponsive Luminescent Molecular Assemblies: An Emerging Class of Materials journal October 2015
Halogen-Assisted Piezochromic Supramolecular Assemblies for Versatile Haptic Memory journal December 2016
Recent progress in the mechanofluorochromism of distyrylanthracene derivatives with aggregation-induced emission journal January 2018
Remarkable pressure-induced emission enhancement based on intermolecular charge transfer in halogen bond-driven dual-component co-crystals journal January 2018
Novel halogen-bonded co-crystals and their unique luminescence property during 10 GPa compression-decompression cycle journal April 2020
Room-Temperature Phosphorescence in Pure Organic Materials: Halogen Bonding Switching Effects journal January 2018
Activating both Halogen and Chalcogen Bonding Interactions in Cation Radical Salts of Iodinated Tetrathiafulavalene Derivatives journal August 2020
Use of Halogen Bonding in a Molecular Solid Solution to Simultaneously Control Spin and Charge journal October 2016
The Halogen Bond: An Emerging Supramolecular Tool in the Design of Functional Mesomorphic Materials journal November 2018
Photoresponsive Halogen-Bonded Liquid Crystals: The Role of Aromatic Fluorine Substitution journal January 2019
Photochemically and Thermally Driven Full-Color Reflection in a Self-Organized Helical Superstructure Enabled by a Halogen-Bonded Chiral Molecular Switch journal January 2018
Visible‐Light‐Driven Halogen Bond Donor Based Molecular Switches: From Reversible Unwinding to Handedness Inversion in Self‐Organized Soft Helical Superstructures journal January 2020
Thienoisoindigo-Based Semiconductor Nanowires Assembled with 2-Bromobenzaldehyde via Both Halogen and Chalcogen Bonding journal September 2018
Impact of Intermolecular Interactions Between a Diketopyrrolopyrrole-Based Conjugated Polymer and Bromobenzaldehyde on Field-Effect Transistors journal January 2021
Selecting Two-Dimensional Halogen–Halogen Bonded Self-Assembled 1,3,5-Tris(4-iodophenyl)benzene Porous Nanoarchitectures at the Solid–Liquid Interface journal August 2013
On-Surface Synthesis of Two-Dimensional Covalent Organic Structures versus Halogen-Bonded Self-Assembly: Competing Formation of Organic Nanoarchitectures journal May 2016
Concentration-Dependent Two-Dimensional Halogen-Bonded Self-Assembly of 1,3,5-Tris(4-iodophenyl)benzene Molecules at the Solid–Liquid Interface journal May 2017
Two-Dimensional Halogen-Bonded Porous Self-Assembled Nanoarchitectures of Copper β-Diketonato Complexes journal March 2018
Two Orthogonal Halogen‐Bonding Interactions Directed 2D Crystalline Supramolecular J‐Dimer Lamellae journal March 2020
Halogen Bonding in Supramolecular Chemistry journal July 2015
Directed Molecular Structure Variations of Three-Dimensional Halogen-Bonded Organic Frameworks (XBOFs) journal January 2018
Highly Interpenetrated Supramolecular Networks Supported by N⋅⋅⋅I Halogen Bonding journal July 2007
Directed synthesis of a halogen-bonded open porphyrin network journal January 2014
Pure Organic Hexagonal–Channels Constructed by C–I··· O–N + Halogen Bond and π–Hole···π Bond under Mediation of Guest journal September 2018
Halogen-Bonded Organic Frameworks of Perfluoroiodo- and Perfluorodiiodobenzene with 2,2′,7,7′-Tetrapyridyl-9,9′-spirobifluorene journal December 2020
Cluster-Based Metal–Organic Frameworks: Modulated Singlet–Triplet Excited States and Temperature-Responsive Phosphorescent Switch journal September 2018
The Morpholinyl Oxygen Atom as an Acceptor Site for Halogen-Bonded Cocrystallization of Organic and Metal–Organic Units journal April 2020
Highly Emissive Covalent Organic Frameworks journal April 2016
Hydrogen-Bonded Organic Frameworks as a Tunable Platform for Functional Materials journal July 2020
Emerging trends in molecular recognition: Utility of weak aromatic interactions journal January 2008
The Nature and Applications of π–π Interactions: A Perspective journal January 2019
Rethinking the term “pi-stacking” journal January 2012
The nature of .pi.-.pi. interactions journal July 1990
Polar/.pi. interactions between stacked aryls in 1,8-diarylnaphthalenes journal July 1992
Aromatic interactions journal January 2001
Structures and Properties of Molecular Torsion Balances to Decipher the Nature of Substituent Effects on the Aromatic Edge-to-Face Interaction journal March 2014
Relative substituent position on the strength of π–π stacking interactions journal March 2010
Synergy between experimental and computational studies of aromatic stacking interactions journal January 2017
Quantification of CH⋅⋅⋅π Interactions: Implications on How Substituent Effects Influence Aromatic Interactions journal September 2010
Substituent effects on aromatic stacking interactions journal January 2007
Enthalpy (Δ H ) and Entropy (Δ S ) for π-Stacking Interactions in Near-Sandwich Configurations:  Relative Importance of Electrostatic, Dispersive, and Charge-Transfer Effects journal March 2007
Substituent Effects in C 6 F 6 C 6 H 5 X Stacking Interactions journal December 2006
Substituent Effects in π−π Interactions:  Sandwich and T-Shaped Configurations journal June 2004
Face-to-Face Arene−Arene Binding Energies: Dominated by Dispersion but Predicted by Electrostatic and Dispersion/Polarizability Substituent Constants journal March 2011
How important are dispersion interactions to the strength of aromatic stacking interactions in solution? journal January 2015
Energy Component Analysis of π Interactions journal June 2012
Local Nature of Substituent Effects in Stacking Interactions journal July 2011
Substituent Effects in the Benzene Dimer are Due to Direct Interactions of the Substituents with the Unsubstituted Benzene journal August 2008
Toward a More Complete Understanding of Noncovalent Interactions Involving Aromatic Rings journal July 2014
Quantum-Mechanical Evaluation of π–π versus Substituent−π Interactions in π Stacking: Direct Evidence for the Wheeler–Houk Picture journal December 2014
Reinterpreting π-stacking journal January 2020
Phase transitions in molecular crystals from a chemical viewpoint journal January 1991
Mechanically induced luminescence changes in molecular assemblies journal October 2009
Recent advances in organic mechanofluorochromic materials journal January 2012
Deformation-Induced Color Changes in Melt-Processed Photoluminescent Polymer Blends journal November 2003
Material Design for Piezochromic Luminescence:  Hydrogen-Bond-Directed Assemblies of a Pyrene Derivative journal February 2007
Molecular-Level Understanding of Structural Changes of Organic Crystals Induced by Macroscopic Mechanical Stimulation journal January 2016
Aggregation-induced emission: phenomenon, mechanism and applications journal January 2009
Aggregation-Induced Emission: Together We Shine, United We Soar! journal October 2015
Journey of Aggregation-Induced Emission Research journal March 2018
Mechanochromic Luminescence of Aggregation-Induced Emission Luminogens journal August 2015
Three polymorphs of one luminogen: how the molecular packing affects the RTP and AIE properties? journal January 2017
Polymorphism-Dependent and Switchable Emission of Butterfly-Like Bis(diarylmethylene)dihydroanthracenes journal September 2015
Drastic Modulation of Stimuli-Responsive Fluorescence by a Subtle Structural Change of Organic Fluorophore and Polymorphism Controlled Mechanofluorochromism journal May 2018
Organic Polymorphs: One-Compound-Based Crystals with Molecular-Conformation- and Packing-Dependent Luminescent Properties journal July 2014
Polymorphism, Mechanofluorochromism, and Photophysical Characterization of a Carbonyl Substituted Difluoroboron-β-Diketone Derivative journal July 2017
High contrast stimuli-responsive luminescence switching of pyrene-1-carboxylic esters triggered by a crystal-to-crystal transition journal January 2017
Dimesitylboryl-functionalised cyanostilbene derivatives of phenothiazine: distinctive polymorphism-dependent emission and mechanofluorochromism journal January 2018
Piezochromic luminescence of amide and ester derivatives of tetraphenylpyrene—role of amide hydrogen bonds in sensitive piezochromic response journal January 2011
Fluorenone Organic Crystals: Two-Color Luminescence Switching and Reversible Phase Transformations between π–π Stacking-Directed Packing and Hydrogen Bond-Directed Packing journal March 2014
Reversible luminescence color switching in the crystal polymorphs of 2,7-bis(2′-methyl-[1,1′-biphenyl]-4-yl)-fluorenone by thermal and mechanical stimuli journal January 2016
Predicting polymorphism in molecular crystals using orientational entropy journal September 2018
Presence of Short Intermolecular Contacts Screens for Kinetic Stability in Packing Polymorphs journal May 2018
Supramolecular Assemblies by Charge-Transfer Interactions between Donor and Acceptor Chromophores journal January 2014
Exploiting the interactions of aromatic units for folding and assembly in aqueous environments journal January 2016
A Systematic Study of Thermochromic Aromatic Donor−Acceptor Materials journal November 2010
Time-Dependent Solid-State Polymorphism of a Series of Donor–Acceptor Dyads journal December 2013
Solution- and solid-state photophysical and stimuli-responsive behavior in conjugated monoalkoxynaphthalene–naphthalimide donor–acceptor dyads journal January 2015
Mechanistic Analysis of Solid-State Colorimetric Switching: Monoalkoxynaphthalene-Naphthalimide Donor–Acceptor Dyads journal September 2020
Rational Control of Charge Transfer Excitons Toward High‐Contrast Reversible Mechanoresponsive Luminescent Switching journal August 2020
Building Blocks for High‐Efficiency Organic Photovoltaics: Interplay of Molecular, Crystal, and Electronic Properties in Post‐Fullerene ITIC Ensembles journal September 2019
Fluorination Effects on Indacenodithienothiophene Acceptor Packing and Electronic Structure, End-Group Redistribution, and Solar Cell Photovoltaic Response journal January 2019
Carpenter’s Rule Folding in Rigid–Flexible Block Copolymers with Conjugation-Interrupting, Flexible Tethers Between Oligophenylenevinylenes journal June 2015
Naphthalenediimide (NDI)-Conjugated Foldable Polyurethanes: Impact of Chromophoric Location on Hierarchical Supramolecular Assembly and Conductivity journal June 2018
Electron-transporting foldable alternating copolymers of perylenediimide and flexible macromolecular chains journal January 2018
Diverse π–π stacking motifs modulate electrical conductivity in tetrathiafulvalene-based metal–organic frameworks journal January 2019
The Organic Secondary Building Unit: Strong Intermolecular π Interactions Define Topology in MIT-25, a Mesoporous MOF with Proton-Replete Channels journal March 2017
Torsional Impacts on Quaterthiophene Segments Confined within Peptidic Nanostructures journal January 2019
Organic Fluorine: Odd Man Out journal April 2004
Fluorine in crystal engineering—“the little atom that could” journal January 2005
Effect of Fluorination on Electronic Properties of Polythienothiophene- co -benzodithiophenes and Their Fullerene Complexes journal August 2014
Fluorinated organic materials for electronic and optoelectronic applications: the role of the fluorine atom journal January 2007
A Molecular Complex of Benzene and Hexafluorobenzene journal September 1960
Intermolecular Interaction between Hexafluorobenzene and Benzene:  Ab Initio Calculations Including CCSD(T) Level Electron Correlation Correction journal February 2006
Dispersion-Corrected Density Functional Theory for Aromatic Interactions in Complex Systems journal June 2012
Assessing the Significance of Hexafluorobenzene as a Unique Guest Agent through Stacking Interactions in Substituted Ethynylphenyl Benzamides journal March 2018
Crystal Engineering of N , N ′-Diphenylurea Compounds Featuring Phenyl–Perfluorophenyl Interaction journal October 2017
Phenyl/Pentafluorophenyl Interactions and the Generation of Ordered Mixed Crystals:sym-Triphenethynylbenzene andsym-Tris(perfluorophenethynyl)benzene journal July 2000
Synthesis and Solid-State Structure of Perfluorophenyl End-Capped Polyynes journal May 2008
Arene-perfluoroarene interactions in crystal engineering: structural preferences in polyfluorinated tolans journal January 2004
Alternating Arene−Perfluoroarene Poly(phenylene ethynylenes) journal May 2007
Aryl−Perfluoroaryl Substituted Tetracene: Induction of Face-to-Face π−π Stacking and Enhancement of Charge Carrier Properties journal April 2011
Luminescence from π–π stacked bipyridines through arene–perfluoroarene interactions journal January 2009
Bithiophene−Perfluorobenzene Copolymers journal November 2008
A Diarylethene Cocrystal that Converts Light into Mechanical Work journal October 2010
Phenyl–Perfluorophenyl Stacking Interactions: A New Strategy for Supermolecule Construction journal February 1997
Soluble Poly(diacetylene)s Using the Perfluorophenyl−Phenyl Motif as a Supramolecular Synthon journal July 2008
Intense solid-state blue emission with a small Stokes’ shift: π-stacking protection of the diphenylanthracene skeleton journal January 2009
Crystalline Alloys of Organic Donors and Acceptors Based on TIPS-Pentacene journal August 2015
Organic Semiconducting Alloys with Tunable Energy Levels journal February 2019
Fluorocarbon-Modified Organic Semiconductors:  Molecular Architecture, Electronic, and Crystal Structure Tuning of Arene- versus Fluoroarene-Thiophene Oligomer Thin-Film Properties journal May 2006
Building Blocks for n-Type Organic Electronics: Regiochemically Modulated Inversion of Majority Carrier Sign in Perfluoroarene-Modified Polythiophene Semiconductors journal August 2003
Molecular cocrystals: design, charge-transfer and optoelectronic functionality journal January 2018
Competition between Arene-Perfluoroarene and Charge-Transfer Interactions in Organic Light-Harvesting Systems journal May 2017
Charge Transfer Versus Arene–Perfluoroarene Interactions in Modulation of Optical and Conductivity Properties in Cocrystals of 2,7-Di- tert -butylpyrene journal July 2019
Epitaxial Growth of Nanorod Meshes from Luminescent Organic Cocrystals via Crystal Transformation journal April 2020
Stabilization of Columnar Liquid Crystal Phases via Arene-Perfluoroarene Interactions journal December 2019
Improving the Overall Properties of Circularly Polarized Luminescent Materials Through Arene–Perfluoroarene Interactions journal January 2021
Aryl-Perfluoroaryl Interaction in Two-Dimensional Organic–Inorganic Hybrid Perovskites Boosts Stability and Photovoltaic Efficiency journal May 2019
Nanoscale Phase Segregation in Supramolecular π-Templating for Hybrid Perovskite Photovoltaics from NMR Crystallography journal January 2021
Side Chain Engineering in Solution-Processable Conjugated Polymers journal September 2013
Twisting and piezochromism of phenylene-ethynylenes with aromatic interactions between side chains and main chains journal January 2014
Substituent Effects That Control Conjugated Oligomer Conformation through Non-covalent Interactions journal March 2017
Reversible mechanofluorochromism of aniline-terminated phenylene ethynylenes journal January 2018
Small Changes With Big Consequences: Swapping Two Atoms In Side Chains Changes Phenylene‐Ethynylene Packing And Fluorescence journal July 2018
Side Chain Regioisomers that Dictate Optical Properties and Mechanofluorochromism through Crystal Packing journal May 2020
Perspectives in Chemistry-Steps towards Complex Matter journal February 2013
Förster Energy Transfer Theory as Reflected in the Structures of Photosynthetic Light‐Harvesting Systems journal February 2011
Digitizing Chemistry Using the Chemical Processing Unit: From Synthesis to Discovery journal December 2020