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

Reversible mechanofluorochromism of aniline-terminated phenylene ethynylenes

Journal Article · · Chemical Science
DOI:https://doi.org/10.1039/C8SC00980E· OSTI ID:1439913

Alkyl chain length tunes the reversion temperature of mechanofluorochromic phenylene-ethynylenes that show reversible force-induced change of fluorescence from green to orange.

Research Organization:
Tufts University, Boston, MA (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
Grant/Contract Number:
SC0016423
OSTI ID:
1439913
Alternate ID(s):
OSTI ID: 1505082
Journal Information:
Chemical Science, Journal Name: Chemical Science Journal Issue: 24 Vol. 9; ISSN 2041-6520; ISSN CSHCBM
Publisher:
Royal Society of ChemistryCopyright Statement
Country of Publication:
United Kingdom
Language:
English

References (101)

Elastoplastic Inverse Opals as Power-Free Mechanochromic Sensors for Force Recording journal August 2015
Mechano‐ and Photochromism from Bulk to Nanoscale: Data Storage on Individual Self‐Assembled Ribbons journal May 2016
Oligo(p-phenylene vinylene)s as a “New” Class of Piezochromic Fluorophores journal January 2008
Luminescent Chromism of Boron Diketonate Crystals: Distinct Responses to Different Stresses journal April 2015
Mechanoresponsive Luminescent Molecular Assemblies: An Emerging Class of Materials journal October 2015
A Triarylboron-Based Fluorescent Thermometer: Sensitive Over a Wide Temperature Range journal July 2011
Controlling Mechano- and Seeding-Triggered Single-Crystal-to-Single-Crystal Phase Transition: Molecular Domino with a Disconnection of Aurophilic Bonds journal November 2013
Multicolor Fluorescence Writing Based on Host-Guest Interactions and Force-Induced Fluorescence-Color Memory journal May 2015
Oligo(p-phenylene-ethynylene)s with Backbone Conformation Controlled by Competitive Intramolecular Hydrogen Bonds journal May 2011
Poly(aryleneethynylene)s journal May 2009
Improved Thin-Film Transistor Performance Through a Melt of Poly(para-phenyleneethynylene) journal September 2014
Investigation of Solvent Effects on Photophysical Properties of New Aminophthalimide Derivatives-Based on Methanesulfonate journal January 2017
Solvent interactions in the excited state of non-planar donor—acceptor molecules journal January 1986
Spectroscopy and photophysics of bridged enone derivatives: effect of molecular structure and solvent journal February 1995
Recent progress in organic mechanoluminescent materials journal February 2018
Influence of alkyl chain lengths on the properties of iridium(III)-based piezochromic luminescent dyes with triazole-pyridine type ancillary ligands journal December 2013
Alkyl length dependent mechanofluorochromism of AIE-based phenothiazinyl fluorophenyl acrylonitrile derivatives journal January 2017
Mechanochromic and acidochromic response of 4H-pyran derivatives with aggregation-induced emission properties journal June 2017
Alkyl length dependent reversible mechanofluorochromism of phenothiazine derivatives functionalized with formyl group journal December 2017
Unusual large Stokes shift and solvatochromic fluorophore: Synthesis, spectra, and solvent effect of 6-substituted 2,3-naphthalimide journal November 2010
An outlook review: Mechanochromic materials and their potential for biological and healthcare applications journal December 2014
Mechanochromic Luminescence Based on Crystal-to-Crystal Transformation Mediated by a Transient Amorphous State journal December 2015
Aggregation-Induced Emission: Together We Shine, United We Soar! journal October 2015
Modulating Mechanochromic Luminescence Quenching of Alkylated Iodo Difluoroboron Dibenzoylmethane Materials journal June 2016
Effect of End Groups on Mechanochromism and Electroluminescence in Tetraphenylethylene Substituted Phenanthroimidazoles journal August 2016
Multi-Stimuli Responsive Donor–Acceptor Tetraphenylethylene Substituted Benzothiadiazoles journal October 2016
Mechanochromic Luminescence of Aggregation-Induced Emission Luminogens journal August 2015
Polymer–Inorganic Composites with Dynamic Covalent Mechanochromophore journal August 2016
Conformationally Locked Tolans, β-Sheet Structures, and Photophysical Properties journal December 2015
Halochromic Isoquinoline with Mechanochromic Triphenylamine: Smart Fluorescent Material for Rewritable and Self-Erasable Fluorescent Platform journal November 2016
Novel Reversible Mechanochromic Elastomer with High Sensitivity: Bond Scission and Bending-Induced Multicolor Switching journal March 2017
Smart Luminescent Coordination Polymers toward Multimode Logic Gates: Time-Resolved, Tribochromic and Excitation-Dependent Fluorescence/Phosphorescence Emission journal May 2017
Mechanochromic Dynamic Covalent Elastomers: Quantitative Stress Evaluation and Autonomous Recovery journal October 2015
Journey of Aggregation-Induced Emission Research journal March 2018
Fluorogenic Polydiacetylene Supramolecules: Immobilization, Micropatterning, and Application to Label-Free Chemosensors journal July 2008
Iptycenes in the Design of High Performance Polymers journal September 2008
Side Chain Engineering in Solution-Processable Conjugated Polymers journal September 2013
Synthesis of Light-Emitting Conjugated Polymers for Applications in Electroluminescent Devices journal March 2009
Vapochromic and Mechanochromic Phosphorescence Materials Based on a Platinum(II) Complex with 4-Trifluoromethylphenylacetylide journal May 2012
Unichromophoric Platinum-Acetylides That Contain Pentiptycene Scaffolds: Torsion-Induced Dual Emission and Steric Shielding of Dynamic Quenching journal December 2013
Fluorescent Chemosensors Based on Energy Migration in Conjugated Polymers: The Molecular Wire Approach to Increased Sensitivity journal December 1995
Steps To Demarcate the Effects of Chromophore Aggregation and Planarization in Poly(phenyleneethynylene)s. 1. Rotationally Interrupted Conjugation in the Excited States of 1,4-Bis(phenylethynyl)benzene journal May 2001
Fluorescent Signaling Based on Control of Excited State Dynamics. Biarylacetylene Fluorescent Chemosensors journal February 2002
Structure−Property Relationships of Donor/Acceptor-Functionalized Tetrakis(phenylethynyl)benzenes and Bis(dehydrobenzoannuleno)benzenes journal March 2005
Material Design for Piezochromic Luminescence:  Hydrogen-Bond-Directed Assemblies of a Pyrene Derivative journal February 2007
Twisted Tethered Tolanes: Unanticipated Long-Lived Phosphorescence at 77 K journal January 2013
Distinct Responses to Mechanical Grinding and Hydrostatic Pressure in Luminescent Chromism of Tetrathiazolylthiophene journal May 2013
Substituent Effects in the Benzene Dimer are Due to Direct Interactions of the Substituents with the Unsubstituted Benzene journal August 2008
Theoretical Interpretation of Conductivity Measurements of a Thiotolane Sandwich. A Molecular Scale Electronic Controller journal April 1998
Fluorescent Porous Polymer Films as TNT Chemosensors:  Electronic and Structural Effects journal November 1998
A Screening Approach for the Discovery of Mechanochromic Gold(I) Isocyanide Complexes with Crystal-to-Crystal Phase Transitions journal May 2016
Molecular Engineering of Mechanochromic Materials by Programmed C–H Arylation: Making a Counterpoint in the Chromism Trend journal September 2016
Regioisomer-Specific Mechanochromism of Naphthopyran in Polymeric Materials journal September 2016
Mechano- and Thermoresponsive Photoluminescent Supramolecular Polymer journal March 2017
Substituent Effects That Control Conjugated Oligomer Conformation through Non-covalent Interactions journal March 2017
Rotaxanes as Mechanochromic Fluorescent Force Transducers in Polymers journal January 2018
Steps To Demarcate the Effects of Chromophore Aggregation and Planarization in Poly(phenyleneethynylene)s. 2. The Photophysics of 1,4-Diethynyl-2-fluorobenzene in Solution and in Crystals journal May 2001
Substituent Effects in C 6 F 6 C 6 H 5 X Stacking Interactions journal December 2006
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
Synthesis, Rotational Dynamics, and Photophysical Characterization of a Crystalline Linearly Conjugated Phenyleneethynylene Molecular Dirotor journal May 2013
Bridged Tolanes: A Twisted Tale journal June 2014
Jacketed Poly( p -phenyleneethynylene)s:  Nonaggregating Conjugated Polymers as Blue-Emitting Rods journal November 2004
Synthesis and Characterization of a Low-Bandgap Poly(arylene ethynylene) Having Donor–Acceptor Type Chromophores in the Side Chain journal February 2013
Bandgap Engineering of Conjugated Materials with Nonconjugated Side Chains journal March 2014
Conformational and Electronic Engineering of Twisted Diphenylacetylenes journal September 2003
Oligo( p -phenyleneethynylene)s with Hydrogen-Bonded Coplanar Conformation journal July 2008
Bio-inspired sensitive and reversible mechanochromisms via strain-dependent cracks and folds journal July 2016
Rewritable phosphorescent paper by the control of competing kinetic and thermodynamic self-assembling events journal June 2005
Reversible piezochromic luminescence of 9,10-bis[(N-alkylcarbazol-3-yl)vinyl]anthracenes and the dependence on N-alkyl chain length journal January 2013
Poly(aryleneethynylene)s (PAE) as paradigmatic sensor cores journal January 2015
Twisting and piezochromism of phenylene-ethynylenes with aromatic interactions between side chains and main chains journal January 2014
Reversible mechanochromic luminescence of phenothiazine-based 10,10′-bianthracene derivatives with different lengths of alkyl chains journal January 2015
Simultaneous modification of N-alkyl chains on cyclometalated and ancillary ligands of cationic iridium( iii ) complexes towards efficient piezochromic luminescence properties journal January 2015
Substituent-dependent backward reaction in mechanofluorochromism of dibenzoylmethanatoboron difluoride derivatives journal January 2016
Mechanochromism and aggregation induced emission in benzothiazole substituted tetraphenylethylenes: a structure function correlation journal January 2015
Significant effect of alkyl chain length on fluorescent thermochromism of 9,10-bis(p-alkoxystyryl)anthracenes journal January 2015
High-contrast mechanochromism and polymorphism-dependent fluorescence of difluoroboron β-diketonate complexes based on the effects of AIEE and halogen journal January 2016
Full-color tunable mechanofluorochromism and excitation-dependent emissions of single-arm extended tetraphenylethylenes journal January 2015
Indene-1,3-dionemethylene-4H-pyran derivatives containing alkoxy chains of various lengths: aggregation-induced emission enhancement, mechanofluorochromic properties and solvent-induced emission changes journal January 2016
Alkyl length effects on solid-state fluorescence and mechanochromic behavior of small organic luminophores journal January 2016
A mechano- and thermoresponsive luminescent cyclophane journal January 2016
Novel time-temperature and ‘consume-within’ indicator based on gas-diffusion journal January 2016
Synergy between experimental and computational studies of aromatic stacking interactions journal January 2017
Fluorene-based mononuclear gold( i ) complexes: the effect of alkyl chain, aggregation-induced emission (AIE) and mechanochromism characteristics journal January 2016
Tuning the thermo- and mechanoresponsive behavior of luminescent cyclophanes journal January 2016
Effect of alkyl length dependent crystallinity for the mechanofluorochromic feature of alkyl phenothiazinyl tetraphenylethenyl acrylonitrile derivatives journal January 2016
Modulation of sensitivity to mechanical stimulus in mechanofluorochromic properties by altering substituent positions in solid-state emissive diiodo boron diiminates journal January 2016
The effect of N-alkyl chain length on the photophysical properties of indene-1,3-dionemethylene-1,4-dihydropyridine derivatives journal January 2016
Reversible thermo-stimulus solid-state fluorescence-colour/on–off switching and uses as sensitive fluorescent thermometers in different temperature ranges journal January 2016
Impact of crystalline packing on the mechanochromic luminescence properties of copper based compounds: towards functional coatings journal January 2016
Controlling solid-state optical properties of stimuli responsive dimethylamino-substituted dibenzoylmethane materials journal January 2017
Mechanofluorochromic properties of fluorescent molecules based on a dicyanomethylene-4H-pyran and indole isomer containing different alkyl chains via an alkene module journal January 2017
Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole journal January 2001
Aggregation-induced emission: phenomenon, mechanism and applications journal January 2009
Alkyl chain length effects on solid-state difluoroboron β-diketonate mechanochromic luminescence journal January 2011
Mechanoresponsive Materials journal January 2011
Multifunctional organic fluorescent materials derived from 9,10-distyrylanthracene with alkoxyl endgroups of various lengths journal January 2012
Solid-state fluorescence properties and reversible piezochromic luminescence of aggregation-induced emission-active 9,10-bis[(9,9-dialkylfluorene-2-yl)vinyl]anthracenes journal January 2013
Cruciform 9,10-distyryl-2,6-bis(p-dialkylamino-styryl)anthracene homologues exhibiting alkyl length-tunable piezochromic luminescence and heat-recovery temperature of ground states journal January 2014
Structure–mechanical property correlations in mechanochromic luminescent crystals of boron difluoride dibenzoylmethane derivatives journal September 2015
Engineering supramolecular photoactive nanomaterials by hydrogen-bonding interactions journal March 2011

Similar Records

Small Changes With Big Consequences: Swapping Two Atoms In Side Chains Changes Phenylene‐Ethynylene Packing And Fluorescence
Journal Article · Thu Oct 25 20:00:00 EDT 2018 · Chemistry - A European Journal · OSTI ID:1479157

Side Chain Regioisomers that Dictate Optical Properties and Mechanofluorochromism through Crystal Packing
Journal Article · Sun May 17 20:00:00 EDT 2020 · Chemistry of Materials · OSTI ID:1656806