Probing metal cations with two new Schiff base bischromophoric pyrene based chemosensors: Synthesis, photophysics and interactions patterns

Castro, Catherine S. P. De; Cova, Tânia F.G.G.; Pais, Alberto A. C. C.; Pinheiro, Daniela; Núñez, Cristina; Lodeiro, Carlos; Melo, J. Sérgio Seixas de

doi:10.1016/j.dyepig.2016.08.016

Cited by 8 publications

(6 citation statements)

References 28 publications

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“…The fluorescence decays were analyzed with sums of exponentials, according to eq 1 , where τ i are the decay times and a i are the preexponential factors that represent the contribution of each exponential term for t = 0. The fractional contribution of each species ( C i ) was determined using eq 2 , 47 with n the number of exponential terms, a i the contribution of each of the exponential terms for t = 0, and τ i the respective decay time. The data are summarized in Table S1 and Figure 2 .…”

Section: Resultsmentioning

confidence: 99%

Aggregation-Induced Emission with Alkynylcoumarin Dinuclear Gold(I) Complexes: Photophysical, Dynamic Light Scattering, and Time-Dependent Density Functional Theory Studies

et al. 2022

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Aggregation-induced emission (AIE) has gained a remarkable amount of interest in the past 20 years, but the majority of the studies are based on organic structures. Herein, three dinuclear gold(I) complexes, with the general formula [PPh 2 XPPh 2 -Au 2 -Coum 2 ], where the Au(I) atom is linked to three different diphosphanes [PPh 2 XPPh 2 ; DPPM for X = CH 2 (1.1), DPPP for X = (CH 2 ) 3 (1.2), and DPPA for X = CC (1.3)] and the propynyloxycoumarin precursor (1, 4-methyl-substituted coumarin), have been synthesized. The compounds present AIE characteristics, AIEgens, with high luminescence quantum yields in the solid state when they are compared to dilute solutions. Photophysical studies (steady-state and time-resolved fluorescence) were obtained, with AIE being observed with the three gold(I) complexes in acetonitrile/water mixtures. This was further corroborated with dynamic light scattering measurements. Time-dependent density functional theory (TDDFT) electronic calculations show that the compounds have different syn and anti conformations (relative to the coumarin core) with 1.1 syn and 1.2 and 1.3 both anti. From time-resolved fluorescence experiments, the augment in the contribution of the longer decay component is found to be associated with the emission of the aggregate (AIE effect) and its nature (involving a dimer) rationalized from TDDFT electronic calculations.

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Section: Resultsmentioning

confidence: 99%

Aggregation-Induced Emission with Alkynylcoumarin Dinuclear Gold(I) Complexes: Photophysical, Dynamic Light Scattering, and Time-Dependent Density Functional Theory Studies

et al. 2022

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“…The photoluminescence (PL) intensity response with time, I ( t ), is given by eq , with decay times, τ i , and pre-exponential factors, a i , where i stands for the number of the exponential I sol false( t false) = ∑ i = 1 n a i normale − t / τ i where τ i terms are the decay times and a i terms are the pre-exponential factors that represent the contribution of each exponential term to t = 0. The fractional contribution of each species [ C i (%)] was determined using eq : C i false( % false) = a i τ i ∑ i = 1 n a i τ i × 100 where n represents the number of exponential terms, a i the contribution of each exponential term, for t = 0, and τ i the associated decay time.…”

Section: Resultsmentioning

confidence: 99%

Practical Design of 3,6-Di-tert-butyldiphenyldibenzofulvene Derivatives with Enhanced Aggregation-Induced Emission

Cunha

Peixoto

Santos

et al. 2022

ACS Appl. Opt. Mater.

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Diphenyldibenzofulvene derivatives consisting of an aromatic tertbutyl-substituted fluorene stator and different rotors consisting of nonsubstituted phenyl groups (3,6-dtb-DPBF) and monomethyl-substituted (3,6-dtb-DPBFMe) and dimethyl-substituted [3,6-dtb-DPBF(Me) 2 ] forms have been synthesized and found to display aggregation-induced emission (AIE). The incremental number of substituents from 3,6-dtb-DPBF to the 3,6-dtb-DPBFMe and 3,6-dtb-DPBF-(Me) 2 derivatives promotes significant changes, from a good solvent (acetonitrile, MeCN), where it is very poorly emissive, to thin films or aggregates, in MeCN/ water mixtures, and a huge increment in fluorescence emission, which is found to be dependent on the water fraction, f w . The characteristics (size and distribution) of the aggregates were further corroborated with dynamic light scattering measurements. From time-resolved fluorescence experiments (TCSPC and FLIM), the increase in the contribution of the longer decay component is linked to the emission of the aggregate (AIE effect). To assist in the elucidation of the aggregation process at a molecular level, the data were complemented with computational studies [time-dependent density functional theory (TDDFT) and molecular dynamics (MD) simulations]. From MD, the octamer properly addresses the properties of the aggregate. As determined by the X-ray data, the crystal structure of a two-unit special disposition is identical to the geometry of the most stable structure obtained from MD and TDDFT calculations.

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“…Due to its versatile and extensively investigated properties, pyrene is well suited as a chemical sensor. [20][21][22][23][24][25][26][27][28][29] Pyrene derivatives functionalized at the 2-position via a one-step iridium-catalyzed reaction with B 2 pin 2 offer significantly longer fluorescence lifetimes in comparison to pyrene derivatives that are functionalized at the 1-position. [30,31] As a chemosensor, in most cases, reports on the analyte in its excited state, the response is enhanced for sensors with longer excited state lifetimes, leading to improved sensitivity.…”

Section: Resultsmentioning

confidence: 99%

“…The reported sensor combines a previously reported glycol precursor [19] with a rigid arrangement of pyrene moieties. Due to its versatile and extensively investigated properties, pyrene is well suited as a chemical sensor [20–29] . Pyrene derivatives functionalized at the 2‐position via a one‐step iridium‐catalyzed reaction with B 2 pin 2 offer significantly longer fluorescence lifetimes in comparison to pyrene derivatives that are functionalized at the 1‐position [30,31] .…”

Section: Resultsmentioning

confidence: 99%

Pyrene‐Based “Turn‐Off” Probe with Broad Detection Range for Cu²⁺, Pb²⁺ and Hg²⁺ Ions

Merz

Kirchner

et al. 2021

Chemistry A European J

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Detection of metals in different environments with high selectivity and specificity is one of the prerequisites of the fight against environmental pollution with these elements. Pyrenes are well suited for the fluorescence sensing in different media. The applied sensing principle typically relies on the formation of intra-and intermolecular excimers, which is however limiting the sensitivity range due to masking of e. g. quenching effects by the excimer emission. Herein we report a highly selective, structurally rigid chemical sensor based on the monomer fluorescence of pyrene moieties bearing triazole groups. This sensor can quantitatively detect Cu 2 + , Pb 2 + and Hg 2 + in organic solvents over a broad concentrations range, even in the presence of ubiquitous ions such as Na + , K + , Ca 2 + and Mg 2 + . The strongly emissive sensor's fluorescence with a long lifetime of 165 ns is quenched by a 1 : 1 complex formation upon addition of metal ions in acetonitrile. Upon addition of a tenfold excess of the metal ion to the sensor, agglomerates with a diameter of about 3 nm are formed. Due to complex interactions in the system, conventional linear correlations are not observed for all concentrations. Therefore, a critical comparison between the conventional Job plot interpretation, the method of Benesi-Hildebrand, and a non-linear fit is presented. The reported system enables the specific and robust sensing of medically and environmentally relevant ions in the healthrelevant nM range and could be used e. g. for the monitoring of the respective ions in waste streams.

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Probing metal cations with two new Schiff base bischromophoric pyrene based chemosensors: Synthesis, photophysics and interactions patterns

Cited by 8 publications

References 28 publications

Aggregation-Induced Emission with Alkynylcoumarin Dinuclear Gold(I) Complexes: Photophysical, Dynamic Light Scattering, and Time-Dependent Density Functional Theory Studies

Aggregation-Induced Emission with Alkynylcoumarin Dinuclear Gold(I) Complexes: Photophysical, Dynamic Light Scattering, and Time-Dependent Density Functional Theory Studies

Practical Design of 3,6-Di-tert-butyldiphenyldibenzofulvene Derivatives with Enhanced Aggregation-Induced Emission

Pyrene‐Based “Turn‐Off” Probe with Broad Detection Range for Cu²⁺, Pb²⁺ and Hg²⁺ Ions

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Probing metal cations with two new Schiff base bischromophoric pyrene based chemosensors: Synthesis, photophysics and interactions patterns

Cited by 8 publications

References 28 publications

Aggregation-Induced Emission with Alkynylcoumarin Dinuclear Gold(I) Complexes: Photophysical, Dynamic Light Scattering, and Time-Dependent Density Functional Theory Studies

Aggregation-Induced Emission with Alkynylcoumarin Dinuclear Gold(I) Complexes: Photophysical, Dynamic Light Scattering, and Time-Dependent Density Functional Theory Studies

Practical Design of 3,6-Di-tert-butyldiphenyldibenzofulvene Derivatives with Enhanced Aggregation-Induced Emission

Pyrene‐Based “Turn‐Off” Probe with Broad Detection Range for Cu2+, Pb2+ and Hg2+ Ions

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Pyrene‐Based “Turn‐Off” Probe with Broad Detection Range for Cu²⁺, Pb²⁺ and Hg²⁺ Ions