Direct local solvent probing by transient infrared spectroscopy reveals the mechanism of hydrogen-bond induced nonradiative deactivation

The hydrogen-bond induced quenching of an excited chromophore is visualised by probing O–H vibrations of the interacting solvent molecules.

• Publication year

  2017

• Venue

  Chemical Science

• Publication date

  2017-05-16

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1039/c7sc00437kPMID 28970892PMCID 5613230
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Ultrafast Elementary Photochemical Processes of Organic Molecules in Liquid Solution.

  2017cited by this paper
• Symmetry-Breaking Charge Transfer and Hydrogen Bonding: Toward Asymmetrical Photochemistry.

  2016cited by this paper
• Differences in the Vibrational Dynamics of H(2)O and D(2)O: Observation of Symmetric and Antisymmetric Stretching Vibrations in Heavy Water.

  2016cited by this paper
• Direct Visualization of Excited-State Symmetry Breaking Using Ultrafast Time-Resolved Infrared Spectroscopy.

  2016cited by this paper
• Study of Heat Transfer Dynamics from Gold Nanorods to the Environment via Time-Resolved Infrared Spectroscopy.

  2016cited by this paper
• Anharmonic exciton dynamics and energy dissipation in liquid water from two-dimensional infrared spectroscopy.

  2016cited by this paper
• Vibrational solvatochromism of nitrile infrared probes: beyond the vibrational Stark dipole approach.

  2016cited by this paper
• Photothermal Science And Techniques

  2016cited by this paper
• Hydrogen bond dynamics in primary alcohols: a femtosecond infrared study.

  2015cited by this paper
• Proton-Coupled Electron Transfer: Moving Together and Charging Forward

  2015cited by this paper
• Hydrogen bond dynamics in bulk alcohols.

  2015cited by this paper
• Pyrrolo[3,2-b]pyrroles-From Unprecedented Solvatofluorochromism to Two-Photon Absorption.

  2015cited by this paper
• Femtosecond mid-infrared study of the reorientation of weakly hydrogen-bonded water molecules.

  2014cited by this paper
• Can non-polar hydrogen atoms accept hydrogen bonds?

  2014cited by this paper
• Studying the Dynamics of Photochemical Reactions via Ultrafast Time-Resolved Infrared Spectroscopy of the Local Solvent.

  2014cited by this paper
• Excited-state dynamics of an environment-sensitive push-pull diketopyrrolopyrrole: major differences between the bulk solution phase and the dodecane/water interface.

  2014cited by this paper
• Vibrational dynamics and solvatochromism of the label SCN in various solvents and hemoglobin by time dependent IR and 2D-IR spectroscopy.

  2014cited by this paper
• Improved super-resolution microscopy with oxazine fluorophores in heavy water.

  2013cited by this paper
• Synthesis and Optical Properties of Tetraaryl‐1,4‐dihydropyrrolo[3,2‐b]pyrroles

  2013cited by this paper
• Water vibrations have strongly mixed intra- and intermolecular character.

  2013cited by this paper
• Experimental evidence of Fermi resonances in isotopically dilute water from ultrafast broadband IR spectroscopy.

  2013cited by this paper
• Concentration and Solvent Effects on the Excited State Dynamics of the Solar Cell Dye D149: The Special Role of Protons

  2013cited by this paper
• A femtosecond fluorescence study of vibrational relaxation and cooling dynamics of UV dyes.

  2012cited by this paper
• Dynamics of water interacting with interfaces, molecules, and ions.

  2012cited by this paper
• Ultrafast vibrational frequency shifts induced by electronic excitations: naphthols in low dielectric media.

  2012cited by this paper
• Proton-coupled electron transfer.

  2012cited by this paper
• Comprehensive data analysis of femtosecond transient absorption spectra: A review

  2012cited by this paper
• Solvent-hindered intramolecular vibrational redistribution.

  2011cited by this paper
• Hydrogen-bond-assisted excited-state deactivation at liquid/water interfaces.

  2011cited by this paper
• Ultrafast excited-state dynamics of eosin B: a potential probe of the hydrogen-bonding properties of the environment.

  2011cited by this paper
• Hydrogen bonding properties of non-polar solvents.

  2010cited by this paper
• Decomposition of vibrational shifts of nitriles into electrostatic and hydrogen-bonding effects.

  2010cited by this paper
• Hydrogen bonding and transfer in the excited state

  2010cited by this paper
• Tuning the excited-state dynamics of GFP-inspired imidazolone derivatives.

  2010cited by this paper
• Ultrafast vibrational Stark-effect spectroscopy: exploring charge-transfer reactions by directly monitoring the solvation shell response.

  2010cited by this paper
• Ultrafast excited-state dynamics of kynurenine, a UV filter of the human eye.

  2009cited by this paper
• Orientational dynamics of transient molecules measured by nonequilibrium two-dimensional infrared spectroscopy.

  2009cited by this paper
• Local Viscosity of Binary Water+Glycerol Mixtures at Liquid/Liquid Interfaces Probed by Time-Resolved Surface Second Harmonic Generation

  2009cited by this paper
• Molecular and electronic structures, infrared spectra, and vibrational assignment for ap and sc conformers of hexafluoro-iso-propanol

  2008cited by this paper
• Direct femtosecond observation of tight and loose ion pairs upon photoinduced bimolecular electron transfer.

  2008cited by this paper
• Excited-state dynamics of nitroperylene in solution: solvent and excitation wavelength dependence.

  2008cited by this paper
• Broadband ultrafast spectroscopy using a photonic crystal fiber: application to the photophysics of malachite green.

  2007cited by this paper
• Variation of the transition dipole moment across the OH stretching band of water

  2007cited by this paper
• Investigation of the influence of solute-solvent interactions on the vibrational energy relaxation dynamics of large molecules in liquids.

  2007cited by this paper
• The Hydrogen Bond and the Water Molecule: The Physics and Chemistry of Water, Aqueous and Bio-Media

  2006cited by this paper
• Charge instability in quadrupolar chromophores: symmetry breaking and solvatochromism.

  2006cited by this paper
• Hydrogen-Transfer Reactions

  2006cited by this paper
• Intramolecular and intermolecular hydrogen-bonding effects on photophysical properties of 2′-aminoacetophenone and its derivatives in solution

  2005cited by this paper
• Elementary steps in excited-state proton transfer.

  2005cited by this paper
• Ultrafast chemistry: using time-resolved vibrational spectroscopy for interrogation of structural dynamics.

  2005cited by this paper
• Pronounced non-Condon effects in the ultrafast infrared spectroscopy of water.

  2005cited by this paper
• Watching Hydrogen Bonds Break: A Transient Absorption Study of Water.

  2004cited by this paper
• Global and target analysis of time-resolved spectra.

  2004cited by this paper
• Using nitrile-derivatized amino acids as infrared probes of local environment.

  2003cited by this paper
• Hydrogen-bonding-induced phenomena in bifunctional heteroazaaromatics.

  2003cited by this paper
• Excited-state proton transfer: from constrained systems to "super" photoacids to superfast proton transfer.

  2002cited by this paper
• Ultrafast hydrogen bonding dynamics and proton transfer processes in the condensed phase

  2002cited by this paper
• Cooling dynamics of an optically excited molecular probe in solution from femtosecond broadband transient absorption spectroscopy

  2001cited by this paper
• DNA excited-state dynamics: ultrafast internal conversion and vibrational cooling in a series of nucleosides.

  2001cited by this paper
• Hydrogen Bonding in 2-Propanol. The Effect of Fluorination †

  2000cited by this paper
• The Solvation of Acetonitrile

  1999cited by this paper
• New aspects of the ultrafast electronic decay of Malachite Green in solution

  1997cited by this paper
• Microscopic Mechanism of Solute−Solvent Energy Dissipation Probed by Picosecond Time-Resolved Raman Spectroscopy

  1997cited by this paper
• Molecular Mechanism of Radiationless Deactivation of Aminoanthraquinones through Intermolecular Hydrogen-Bonding Interaction with Alcohols and Hydroperoxides

  1997cited by this paper
• Vibrational cooling after ultrafast photoisomerization of azobenzene measured by femtosecond infrared spectroscopy

  1997cited by this paper
• An Introduction to Hydrogen Bonding

  1997cited by this paper
• Pump-probe polarization anisotropy study of femtosecond energy transfer within the photosynthetic reaction center of Rhodobacter sphaeroides R26

  1996cited by this paper
• DIFFUSIVE TORSIONAL DYNAMICS OF MALACHITE GREEN MOLECULES IN SOLID MATRICES PROBED BY FLUORESCENCE DECAY

  1995cited by this paper
• INFRARED PROBE OF THE SOLVENT RESPONSE TO ULTRAFAST SOLVATION PROCESSES

  1995cited by this paper
• Vibrational relaxation dynamics in solutions.

  1994cited by this paper
• The properties of organic liquids that are relevant to their use as solvating solvents

  1994cited by this paper
• ENERGY FLOW FROM SOLUTE TO SOLVENT PROBED BY FEMTOSECOND IR SPECTROSCOPY :MALACHITE GREEN AND HEME PROTEIN SOLUTIONS

  1994cited by this paper
• Femtosecond laser study of energy disposal in the solution phase isomerization of stilbene

  1990cited by this paper
• Raman and far-infrared spectra of gaseous 1,1,1,3,3,3-hexafluoro-2-propanol, conformational stability and barriers to internal rotation

  1988cited by this paper
• Fluorescence studies of the intramolecularly hydrogen-bonded molecules o-hydroxyacetophenone and salicylamide and related molecules

  1986cited by this paper
• Molecular dynamics simulations of cooling in laser-excited heme proteins.

  1986cited by this paper
• Proton transfer and hydrogen bonding in the internal conversion of S1 anthraquinones

  1985cited by this paper
• Effect of librational motion on fluorescence depolarization and nuclear magnetic resonance relaxation in macromolecules and membranes.

  1980cited by this paper
• Hydrogen bond

  1977cited by this paper
• Picosecond recovery dynamics of malachite green

  1976cited by this paper
• The solvatochromic comparison method. 2. The .alpha.-scale of solvent hydrogen-bond donor (HBD) acidities

  1976cited by this paper
• Spectroscopy with Polarized Light

  1966cited by this paper
• Elementary Steps in Excited-state Proton Transfer †

  year unknowncited by this paper

• 2-Aminopyrimidine derivatives as potential fluorescent chemosensors for trivalent cations: Structural characterization, photophysical properties, and live-cell imaging

  2025cites this paper
• The effect of acceptor-donor-acceptor molecule bending on the symmetry breaking charge transfer and transition dipole moment.

  2025cites this paper
• Photoinduced Intramolecular [2 + 2] Cycloaddition Investigated with Transient Infrared Spectroscopy.

  2025cites this paper
• Size-control synthesis of graphene quantum dots in SBA-15 micro-reactor and fabrication of imprinted polymer-based fluorescence sensor for bisphenol A recognition

  2025cites this paper
• Mechanical and Light Activation of Materials for Chemical Production

  2025cites this paper
• 1,4-Dihydropyrrolo[3,2-b]pyrrole modified with dibenzoxazepine: a highly efficient core for charge-transfer-based OLED emitters

  2025cites this paper
• Effect of the Locally Excited State on Symmetry-Breaking Charge Transfer and Transition Dipole Moment in Quadrupolar Molecules with Inverse Level Order.

  2025cites this paper
• Solvent-Induced Silver Nanoclusters/BODIPY Derivative Assembly: Self-sorting and Multi-Structures Enhanced Circularly Polarized Luminescence Properties

  2025cites this paper
• Beyond the Stokes shift: Quantifying excited-state symmetry breaking effects in steady-state spectra of quadrupolar molecules.

  2025cites this paper
• A rapid access to activity-based and mitochondria targeting rhodol-like chromenoxanthene dyes for selective bioimaging

  2024cites this paper
• Effect of locally excited state on fluorescence transition dipole moment in quadrupolar molecules subjected to symmetry breaking charge transfer.

  2024cites this paper
• Tetraarylpyrrolo[3,2-b]pyrrole-BODIPY dyad: a molecular rotor for FRET-based viscosity sensing

  2024cites this paper
• Structural and solvent modulation of symmetry-breaking charge-transfer pathways in molecular triads

  2024cites this paper
• Fluorimetric Tool to Discriminate Glomerular and Tubular Injuries In Vivo.

  2024cites this paper
• Excited-state symmetry breaking is an ultrasensitive tool for probing microscopic electric fields

  2024cites this paper
• Fast and accurate identification of pathogenic bacteria using excitation–emission spectroscopy and machine learning

  2024cites this paper
• Strongly Polarized π-Extended 1,4-Dihydropyrrolo[3,2-b]pyrroles Fused with Tetrazolo[1,5-a]quinolines

  2024cites this paper
• Symmetry breaking charge transfer in excited multibranched molecules and dimers: A unified standpoint

  2024cites this paper
• New insights into the excited state of an A-D-A quadrupolar molecule strongly hydrogen bonded to molecules of methanol and hexafluoro isopropanol

  2023cites this paper
• Quadrupolar, Highly Polarized Dyes: Emission Dependence on Viscosity and Selective Mitochondria Staining

  2023cites this paper
• New pyrrolo[3,2-b]pyrroles with AIE characteristics for detection of dichloromethane and chloroform.

  2023cites this paper
• Electric dipole flip in a quadrupolar molecule with broken symmetry upon excited state absorption.

  2023cites this paper
• Symmetry-breaking charge transfer in an excited acridine-dione derivative: Effects of hydrogen bonding, clustering, and cooperativity in mixtures of methanol and dimethylformamide

  2023cites this paper
• Looking for chiral recognition in photoinduced bimolecular electron transfer using ultrafast spectroscopy

  2023cites this paper
• Fluorescence Modulation by Amines: Mechanistic Insights into Twisted Intramolecular Charge Transfer (TICT) and Beyond

  2023cites this paper
• From 2,5-Diformyl-1,4-dihydropyrrolo[3,2-b]pyrroles to Quadrupolar, Centrosymmetric Two-Photon-Absorbing A–D–A Dyes

  2022cites this paper
• Minimal model of excited-state symmetry breaking in symmetric dimers and covalently linked dyads.

  2022cites this paper
• Triple Emission of 5'-(para-R-Phenylene)vinylene-2-(2'-hydroxyphenyl)benzoxazole (PVHBO). Part I: Dual Emission from the Neutral Species.

  2022cites this paper
• The Pursuit of Shortwave Infrared-Emitting Nanoparticles with Bright Fluorescence through Molecular Design and Excited-State Engineering of Molecular Aggregates

  2022cites this paper
• Watching Excited-State Symmetry Breaking in Multibranched Push-Pull Molecules.

  2022cites this paper
• Modeling the Effect of H-Bonding of Excited Quadrupolar Molecules with a Solvent on Charge Transfer Symmetry Breaking.

  2022cites this paper
• Alkoxy-Substituted Quadrupolar Fluorescent Dyes.

  2022cites this paper
• Going beyond the borders: pyrrolo[3,2-b]pyrroles with deep red emission

  2021cites this paper
• Hydroxyaromatic Fluorophores

  2021cites this paper
• Excited-State Symmetry Breaking and the Laporte Rule.

  2021cites this paper
• Symmetry Breaking in an Excited Quadrupolar Acridine-Dione Derivative Driven by Hydrogen Bonding.

  2021cites this paper
• The role of twisting in driving excited-state symmetry breaking and enhanced two-photon absorption in quadrupolar cationic pyridinium derivatives.

  2021cites this paper
• Synthesis of Novel 1,4-dihydro-1,2,4,5-tetraarylpyrrolo[3,2-b]pyrroles Derivatives Catalyzed by NbCl5 and Application in Dye Sensitized Solar Cells

  2021cites this paper
• Effect of Symmetry Breaking in Excited Quadrupole Molecules on Transition Dipole Moment.

  2021cites this paper
• Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

  2020cites this paper
• Critical Role of Protons for Emission Quenching of Indoline Dyes in Solution and on Semiconductor Surfaces

  2020cites this paper
• Broadband fluorescence reveals mechanistic differences in excited-state proton transfer to protic and aprotic solvents†

  2020cites this paper
• Untying the Photophysics of Quinolinium-Based Molecular Knots and Links.

  2020cites this paper
• Method for the Large-Scale Synthesis of Multifunctional 1,4-Dihydro-pyrrolo[3,2-b]pyrroles

  2020cites this paper
• Bimolecular photoinduced electron transfer in non-polar solvents beyond the diffusion limit.

  2020cites this paper
• Change of Quadrupole Moment upon Excitation and  Symmetry Breaking in Multibranched Donor-Acceptor Dyes.

  2020cites this paper
• Theoretical Insights into the Excited State Decays of a Donor-Acceptor Dyad: Is the Twisted and Rehybridized Intramolecular Charge-Transfer State Involved?

  2020cites this paper
• Spectroscopic, elastic, magnetic and optical studies of nanocrystallite and nanoferro-fluids Co ferrites towards optoelectronic applications

  2020cites this paper
• Universal quenching of common fluorescent probes by water and alcohols

  2020cites this paper
• Ground‐ and Excited‐State Symmetry Breaking and Solvatofluorochromism in Centrosymmetric Pyrrolo[3,2‐ b ]pyrroles Possessing two Nitro Groups

  2020cites this paper
• Fe(iii)-Catalyzed synthesis of pyrrolo[3,2-b]pyrroles: formation of new dyes and photophysical studies

  2019cites this paper
• The full dynamics of energy relaxation in large organic molecules: from photo-excitation to solvent heating

  2019cites this paper
• Regium bonds formed by MX (M═Cu, Ag, Au; X═F, Cl, Br) with phosphine-oxide/phosphinous acid: comparisons between oxygen-shared and phosphine-shared complexes

  2019cites this paper
• Electronic Communication in Pyrrolo[3,2-b ]pyrroles Possessing Sterically Hindered Aromatic Substituents

  2019cites this paper
• The mechanisms of boronate ester formation and fluorescent turn-on in ortho-aminomethylphenylboronic acids

  2019cites this paper
• Stimuli responsive aggregation-induced emission of bis(4-((9H-fluoren-9-ylidene)methyl)phenyl)thiophene single crystals

  2019cites this paper
• Probing the self-assembly dynamics and internal structure of amphiphilic hyaluronic acid conjugates by fluorescence spectroscopy and molecular dynamics simulations.

  2018cites this paper
• Arresting "Loose Bolt" Internal Conversion from -B(OH)2 Groups is the Mechanism for Emission Turn-On in ortho-Aminomethylphenylboronic Acid-Based Saccharide Sensors.

  2018cites this paper
• Development of colloidally stable carbazole-based fluorescent nanoaggregates.

  2018cites this paper
• Dibenzothienopyrrolo[3,2-b]pyrrole: The Missing Member of the Thienoacene Family.

  2018cites this paper
• Transient Glass Formation around a Quadrupolar Photoexcited Dye in a Strongly H-Bonding Liquid Observed by Transient 2D-IR Spectroscopy.

  2018cites this paper
• A theoretical investigation on Cu/Ag/Au bonding in XH2P⋯MY(X = H, CH3, F, CN, NO2; M = Cu, Ag, Au; Y = F, Cl, Br, I) complexes.

  2018cites this paper
• Synthesis of Bis(arylethynyl)pyrrolo[3,2-b]pyrroles and Effect of Intramolecular Charge Transfer on Their Photophysical Behavior.

  2018cites this paper
• High Photostability in Nonconventional Coumarins with Far-Red/NIR Emission through Azetidinyl Substitution.

  2018cites this paper
• Ultrafast excited state decay of natural UV filters: from intermolecular hydrogen bonds to a conical intersection.

  2018cites this paper
• The Tetraarylpyrrolo[3,2-b]pyrroles-From Serendipitous Discovery to Promising Heterocyclic Optoelectronic Materials.

  2017cites this paper
• Direct Observation of a Photochemical Alkyne-Allene Reaction and of a Twisted and Rehybridized Intramolecular Charge-Transfer State in a Donor-Acceptor Dyad.

  2017cites this paper
• Solute-Solvent Interactions and Excited-State Symmetry Breaking: Beyond the Dipole-Dipole and the Hydrogen-Bond Interactions.

  2017cites this paper
• Photolabile coumarins with improved efficiency through azetidinyl substitution† †Electronic supplementary information (ESI) available: Experimental details, ESI figures and NMR spectra. See DOI: 10.1039/c7sc03627b

  2017cites this paper