← Back to Search
Installation/modulation Of The Emission Response Via Click Reaction.
S. Bag, R. Kundu
Published 2011 · Chemistry, Medicine
Save to my Library
Download PDFAnalyze on Scholarcy
We have demonstrated the installation of a fluorescence property into a nonfluorescent precursor and modulation of an emission response of a pyrene fluorophore via click reaction. The synthesized fluorophores show different solvatochromicity and/or intramolecular charge transfer (ICT) feature as is revealed from the UV-visible, fluorescence photophysical properties of these fluorophores, and DFT/TDDFT calculation. We observed that some of the synthesized fluorophores showed purely ICT character while emission from some of them arose from the LE state. A structureless and solvent polarity-sensitive dual emission behavior was observed for one of the triazolylpyrene fluorophores that contains an electron-donating -NMe(2) substituent (fluorophore, 7a). Conversely, triazolylpyrene with an electron-withdrawing -CN group (fluorophore, 7b) showed a solvent polarity-independent vibronic emission. The effect of ICT on the photophysical properties of these fluorophores was studied by fluorescence emission spectra and DFT/TDDFT calculations. Fluorescence lifetimes were also measured in different solvents. All of our findings revealed the delicate interplay of structure and emission properties and thus having broader general utility. As the CT to LE intensity ratio can be employed as a sensing index, the dual emissive fluorophore can be utilized in designing the molecular recognition system too. We envisage that our investigation is of importance for the development of new fluorophores with predetermined photophysical properties that may find a wide range of applications in chemistry, biology, and material sciences.
This paper references
A Fluorogenic Probe for the Copper(I)-Catalyzed Azide−Alkyne Ligation Reaction: Modulation of the Fluorescence Emission via 3(n,π*)−1(π,π*) Inversion
Z. Zhou (2004)
Photophysical properties of 1-N-methylamino- and 1-N,N-dimethylamino-9,10-anthraquinone dyes: A comparison with 1-amino-9,10-anthraquinone dye
P. Dahiya (2007)
Intramolecular Delayed Fluorescence as a Tool for Imaging Science: Synthesis and Photophysical Properties of a First-Generation Emitter
A. Benniston (2007)
Unusual Photophysical Properties of Coumarin-151
Sanjukta Nad and (2001)
Photophysical Properties of Coumarin-30 Dye in Aprotic and Protic Solvents of Varying Polarities¶
S. Senthilkumar (2004)
Solvent effects on the structure of fluorescent 'exciplexes' in rigidly-, flexibly-, and nonbridged donor-acceptor systems
J. Verhoeven (1993)
Photophysical properties of coumarin-500 (C500): Unusual behavior in nonpolar solvents
S. Nad (2003)
A general purpose reporter for cations: absorption, fluorescence and electrochemical sensing of zinc(II)
A. Benniston (2003)
Photochromism of styryl cyanine dyes in solution
N. Sertova (1998)
Solvent polarity and intramolecular hydrogen bonding effects on the photophysical properties of 1-amino-9,10-anthraquinone dye
P. Dahiya (2006)
Solvent Effects upon Fluorescence Spectra and the Dipolemoments of Excited Molecules
N. Mataga (1956)
A molecular 1 : 2 demultiplexer.
E. Pérez-Inestrosa (2008)
Excited-State Photophysics and Dynamics of a Hemicyanine Dye in AOT Reverse Micelles
J. Kim (1999)
Rapid synthesis, screening, and identification of xanthone- and xanthene-based fluorophores using click chemistry.
Junqi Li (2009)
Fluorescent analogs of biomolecular building blocks: design, properties, and applications.
Renatus W. Sinkeldam (2010)
Oligonucleotides containing new fluorescent 1-phenylethynylpyrene and 9,10-bis(phenylethynyl)anthracene uridine-2′-carbamates: synthesis and properties
Natalia N. Dioubankova (2004)
A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes.
V. Rostovtsev (2002)
Structural changes accompanying intramolecular electron transfer: focus on twisted intramolecular charge-transfer states and structures.
Z. Grabowski (2003)
Effect of the amino and hydroxy substituents on the photophysical properties of 1,4-disubstituted-9,10-anthraquinone dyes
P. Dahiya (2006)
Click chemistry and bioorthogonal reactions: unprecedented selectivity in the labeling of biological molecules.
M. Best (2009)
Synthesis and spectroscopic investigation of aggregation through cooperative pi-pi and C-H...O interactions in a novel pyrene octaaldehyde derivative.
G. Venkataramana (2006)
24. Polynuclear heterocyclic systems. Part IX. n-π*-Transitions in the spectra of aromatic aza-hydrocarbons
G. Badger (1956)
A fluorogenic ‘click’ reaction of azidoanthracene derivatives
F. Xie (2008)
The photophysical properties of a pyrene–thiophene–terpyridine conjugate and of its zinc(II) and ruthenium(II) complexes
A. Benniston (2004)
Cu-catalyzed azide-alkyne cycloaddition.
M. Meldal (2008)
Solvent dependence of the photochemistry of the styrylpyridinium dye RH421.
T. H. N. Phạm (2008)
Effect of solvent polarity on the photophysical properties of coumarin-1 dye
A. Barik (2003)
Synthesis, Absorption, and Fluorescence‐Emission Properties of 1,3,6,8‐Tetraethynylpyrene and Its Derivatives
G. Venkataramana (2005)
The use of a monoorganotin derivative of pyrene in the palladium(0)-catalyzed synthesis of a new metal-cation complexing molecule displaying excited state charge transfer properties
A. L. Rodriguez (1998)
A fluorogenic, nucleic acid directed "click" reaction.
Elmar Jentzsch (2009)
Ionic photodissociation of electron donor-acceptor systems in solution
H. Masuhara (1981)
Cu2+-induced intermolecular static excimer formation of pyrenealkylamine.
H. Kim (2008)
Highly Emissive π-Conjugated Alkynylpyrene Oligomers: Their Synthesis and Photophysical Properties
Hisao Shimizu (2007)
Photophysical Properties of Fluorescence Probes. 2. A Model of Multiple Fluorescence for Stilbazolium Dyes Studied by Global Analysis and Quantum Chemical Calculations
B. Strehmel (1997)
Femtosecond solvation dynamics determining the band shape of stimulated emission from a polar styryl dye
D. Bingemann (1995)
Theoretical study on the dual fluorescence of 2-(4-cyanophenyl)-N,N-dimethylaminoethane and its deactivation pathway.
X. Chen (2009)
Cu(I)-catalyzed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction in nucleoside, nucleotide, and oligonucleotide chemistry.
F. Amblard (2009)
Site-selective photoinduced electron transfer from alcoholic solvents to the chromophore facilitated by hydrogen bonding: a new fluorescence quenching mechanism.
G. Zhao (2007)
Electronic polarization reversal and excited state intramolecular charge transfer in donor/acceptor ethynylpyrenes.
Shu-Wen Yang (2005)
Reversal in solvatochromism in some novel styrylpyridinium dyes having a hydrophobic cleft.
M. Panigrahi (2007)
Photophysics of some styryl thiazolo quinoxaline dyes in organic media
A. S. Koti (2000)
Monopole-Dipole Model for Symmetrical Solvatochromism of Hemicyanine Dyes
P. Fromherz (1995)
Effect of solvent polarity on the aggregation of fullerenes: a comparison between C60 and C70
S. Nath (2002)
Combinatorial rosamine library and application to in vivo glutathione probe.
Young-Hoon Ahn (2007)
Photophysical Studies on the Mono- and Dichromophoric Hemicyanine Dyes I. Photoelectric Conversion from the Dye Modified ITO Electrodes
Y. Huang (2002)
Femtosecond Stokes shift in styryl dyes: Solvation or intramolecular relaxation?
S. Kovalenko (1997)
Design of base-discriminating fluorescent nucleosides
A. Okamoto (2005)
Comparison of photophysical properties of the hemicyanine dyes in ionic and nonionic solvents.
Tae-Kyu Shim (2008)
Alkynylpyrenes as improved pyrene-based biomolecular probes with the advantages of high fluorescence quantum yields and long absorption/emission wavelengths.
H. Maeda (2006)
Two-photon absorption properties of alkynyl-conjugated pyrene derivatives.
H. Kim (2008)
Contrasting solvent polarity effect on the photophysical properties of two newly synthesized aminostyryl dyes in the lower and in the higher solvent polarity regions.
M. Shaikh (2010)
Dual Fluorescence from N6,N6-Dimethyladenosine
B. Albinsson (1997)
Switching of the fluorescence emission of single molecules between the locally excited and charge transfer states
M. A. Izquierdo (2005)
High-throughput screens for fluorescent dye discovery.
Vebjorn Ljosa (2008)
This paper is referenced by
Design and Synthesis of Triazolyl‐Donor/Acceptor Unnatural Nucleosides and Oligonucleotide Probes Containing Triazolyl‐Phenanthrene Nucleoside
S. Bag (2014)
Triazolyl C-nucleosides via the intermediacy of β-1′-ethynyl-2′-deoxyribose derived from a Nicholas reaction: Synthesis, photophysical properties and interaction with BSA
S. Bag (2019)
Triazolyl donor/acceptor chromophore decorated unnatural nucleosides and oligonucleotides with duplex stability comparable to that of a natural adenine/thymine pair.
S. Bag (2013)
Sensing the chemical cleavage of fluorescent β-lactams via FRET/exciplex or excimer emission
S. Bag (2018)
Triazolyl-donor-acceptor chromophore-decorated unnatural amino acids and peptides: FRET events in a β-turn conformation.
S. Bag (2014)
Clicked polycyclic aromatic hydrocarbon as a hybridization-responsive fluorescent artificial nucleobase in pyrrolidinyl peptide nucleic acids
Woraluk Mansawat (2012)
Structure-Property Relationships in Click-Derived Donor-Triazole-Acceptor Materials.
Paul Kautny (2016)
Development of functionalized cyclotriveratrylene analogues: introduction of withdrawing and π-conjugated groups.
Lisa Peyrard (2012)
Highly solvatochromic fluorescent naphthalimides: design, synthesis, photophysical properties and fluorescence switch-on sensing of ct-DNA.
S. Bag (2013)
Microstructure and properties of novel fluorescent pyrene functionalized PANI/P(VDF‐HFP) blend
Veer Pal Singh (2014)
Recent advances in organic dyes and fluorophores comprising a 1,2,3-triazole moiety
Damien Brunel (2020)
Tricarbonylrhenium complexes from 2-pyridyl-1,2,3-triazole ligands bearing a 4-substituted phenyl arm: a combined experimental and theoretical study.
M. Wolff (2013)
Efficient and straightforward click synthesis of structurally related dendritic triazoles
M. I. Mangione (2017)
A highly selective fluorescent chemosensor for Ag+ based on calixarene with lower-rim proximal triazolylpyrenes
N. Wang (2012)
Design of a fused triazolyl 2-quinolinone unnatural nucleoside via tandem CuAAC-Ullmann coupling reaction and study of photophysical property
S. Bag (2018)
Solvatochromic fluorescent cyanophenoxazine: design, synthesis, photophysical properties and fluorescence light-up sensing of ct-DNA
S. Bag (2013)
Donor/acceptor chromophores-decorated triazolyl unnatural nucleosides: synthesis, photophysical properties and study of interaction with BSA.
S. Bag (2016)
Synthesis and Photophysical Properties of Push–Pull Structures Incorporating Diazines as Attracting Part with a Fluorene Core
Charline Denneval (2013)
Mono substituted pyrenes as multifunctional materials for OLED: Analysis of the substituent effects on the charge transport properties using DFT methods
Niveditha Surukonti (2018)
Fluorometric sensing of Cu2+ ion with smart fluorescence light-up probe, triazolylpyrene (TNDMBPy)
S. Bag (2012)
Design strategies for bioorthogonal smart probes.
Peyton Shieh (2014)
A convenient [2+2] cycloaddition–cycloreversion reaction for the synthesis of 1,1-dicyanobuta-1,3-diene-scaffolded peptides as new imaging chromophores
D. Rijkers (2011)
Efficient synthesis of novel 6-substituted 2-(4-aryl-1,2,3-triazol-1-yl)pyrimidines and 7-deazapurines*
V. Jakubkienė (2018)
Tunable single and dual emission behavior of imidazole fluorophores based on D-π-A architecture
N. Nagarajan (2014)
One “Click” access to self-complementary molecular modules for halogen bonding
G. Cavallo (2016)
Sensing of Micellar Microenvironment with Dual Fluorescent Probe, Triazolylpyrene (TNDMBPy)
S. Bag (2013)
One “Click” to Access Push–Triazole–Pull Fluorophores Incorporating a Pyrimidine Moiety: Structure–Photophysical Properties Relationships
Anne‐Sophie Cornec (2013)
Functional organic click-materials: application in phosphorescent organic light emitting diodes
Paul Kautny (2017)
Reactions of Malonothioamide Derivatives with Azides*
L. N. Dianova (2014)
Synthesis and Characterization of Fluorescent Nanojars
Liyana Gunawardana (2018)
Polymer anchored Cu(II) complex: an efficient and recyclable catalytic system for the one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles starting from anilines in water
S. Roy (2013)
Synthesis and Photophysical Studies on N1-(2'-O,4'-C-Methyleneribofurano-nucleoside-3'-yl)-C4-(coumarin-7-oxymethyl)-1,2,3-triazoles.
S. Srivastava (2018)See more