Energy Transfer in Dendritic Systems Having Pyrene Peripheral Groups as Donors and Different Acceptor Groups

Porcu, Pasquale; Vonlanthen, Mireille; Ruiu, Andrea; González-Méndez, Israel; Rivera, Ernesto

doi:10.3390/polym10101062

Cited by 15 publications

(5 citation statements)

References 128 publications

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“…In the presence of 2D BP, the emission spectra of all pyrenes show a slight bathochromic shift of the bands (by +2 nm) and an evident change in the intensity ratio of the first to third vibronic emission bands (I/III ratio), more evident for PBA and PBE. Since for this class of compound, the I/III intensities ratio is very sensitive to the solvent polarity, ,,,,− the different emission profiles of the fluorophores in the adducts with respect to free ones can be ascribed to a change of the local environment polarity because of the presence of 2D BP. Even if the emission spectra are not corrected for the absorbance of the samples, an evident increase of the emission intensity has been observed.…”

Section: Results and Discussionmentioning

confidence: 99%

Noncovalent Functionalization of 2D Black Phosphorus with Fluorescent Boronic Derivatives of Pyrene for Probing and Modulating the Interaction with Molecular Oxygen

Bolognesi

Moschetto

Trapani

et al. 2019

ACS Appl. Mater. Interfaces

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We studied the chemical–physical nature of interactions involved in the formation of adducts of two-dimensional black phosphorus (2D BP) with organoboron derivatives of a conjugated fluorescent molecule (pyrene). Time-resolved fluorescence spectroscopy showed a stabilization effect of 2D BP on all derivatives, in particular for the adducts endowed with the boronic functionalities. Also, a stronger modulation of the fluorescence decay with oxygen was registered for one of the adducts compared to the corresponding organoboron derivative alone. Nuclear magnetic resonance experiments in suspension and density functional theory simulations confirmed that only noncovalent interactions were involved in the formation of the adducts. The energetic gain in their formation arises from the interaction of P atoms with both C atoms of the pyrene core and the B atom of the boronic functionalities, with a stronger contribution from the ester with respect to the acid one. The interaction results in the lowering of the band gap of 2D BP by around 0.10 eV. Furthermore, we demonstrated through Raman spectroscopy an increased stability toward oxidation in air of 2D BP in the adducts in the solid state (more than 6 months). The modification of the electronic structure at the interface between 2D BP and a conjugated organic molecule through noncovalent stabilizing interactions mediated by the B atom is particularly appealing in view of creating heterojunctions for optoelectronic, photonic, and chemical sensing applications.

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Section: Results and Discussionmentioning

confidence: 99%

Noncovalent Functionalization of 2D Black Phosphorus with Fluorescent Boronic Derivatives of Pyrene for Probing and Modulating the Interaction with Molecular Oxygen

Bolognesi

Moschetto

Trapani

et al. 2019

ACS Appl. Mater. Interfaces

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“…In addition, molecules having a donor-acceptor structure exhibit large Stokes-shifted fluorescence owing to the effective spatial separation of HOMO and LUMO [34]. The Förster resonance energy transfer (FRET) is a well-known energy transfer phenomenon [35], in which the excitation energy between two chromophores in close distance is directly transferred through non-radiative dipole-dipole coupling, and has been applied to white light-emitting materials [36]. We have also reported a white-light fluorescent PI copolymer based on FRET and room-temperature phosphorescence [8].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of White-Light Luminescent End-Capped Polyimides Based on FRET and Excited State Intramolecular Proton Transfer

et al. 2021

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N-cyclohexylphthalimide-substituted trifluoroacetylamino (CF3CONH-) group (3TfAPI), which forms an intramolecular hydrogen bond, was synthesized, and it exhibited a bright yellow fluorescence owing to the excited-state intramolecular proton transfer (ESIPT) in the solution and crystalline states. In addition, CF3CONH-substituted phthalic anhydride (3TfAPA) was synthesized, which was attached to the termini of a blue-fluorescent semi-aromatic polyimide (PI) chain. Owing to the efficient Förster resonance energy transfer (FRET) occurring from the main chain to the termini and the suppression of deprotonation (anion formation) at the 3TfAPA moiety by H2SO4 doping, the resulting PI films display bright white fluorescence. Moreover, the enhancement of the chain rigidity by substituting the diamine moiety results in an increase in the quantum yield of white fluorescence (Φ) by a factor of 1.7, due to the suppression of local molecular motion. This material design strategy is promising for preparing thermally stable white-light fluorescent PIs applicable to solar spectral convertors, displays, and ICT devices.

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“…Pyrene excimer emission has been used as a fluorescent probe to investigate the local volume and internal dynamics (ID) of polymer chains and dendrimers in solution [ 20 , 21 , 22 ]. The coexistence of monomer and excimer emission bands has allowed investigations into numerous applications in organic electronic devices [ 23 , 24 ], protein conformation [ 25 ], and chemosensing [ 26 ]. Pyrene fluorophore has been included as a comonomer in polymeric materials to yield photoluminescent thermosensitive N-isopropyl acrylamide (NIPAAm) hydrogels [ 27 ], multi-responsive starPEG hydrogels [ 28 ], conductive self-healing hydrogel composites [ 29 ], and fluorescent polymeric chemosensors [ 30 ].…”

Section: Introductionmentioning

confidence: 99%

Facile Obtainment of Fluorescent PEG Hydrogels Bearing Pyrene Groups by Frontal Polymerization

et al. 2023

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Frontal polymerization (FP) was used to prepare poly(ethylene glycol) methyl ether acrylate (PEGMA) fluorescent polymer hydrogels containing pyrenebutyl pendant groups as fluorescent probes. The polymerization procedure was carried out under solvent-free conditions, with different molar quantities of pyrenebutyl methyl ether methacrylate (PybuMA) and PEGMA, in the presence of tricaprylmethylammonium (Aliquat 336®) persulfate as a radical initiator. The obtained PEGPy hydrogels were characterized by FT-IR spectroscopy, confirming the effective incorporation of the PybuMA monomer into the polymer backbone. The thermal properties of the hydrogels were determined using thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). After immersing the hydrogels in deionized water at 25 °C and pH = 7, their swelling behavior was investigated by mass gain at different pH and temperature values. The introduction of PybuMA comonomer into the hydrogel resulted in a decreased swelling ability due to the hydrophobicity of PybuMA. The optical properties of PEGPy were determined by UV-visible absorption and fluorescence spectroscopies. Both monomer and excimer emission bands were observed at 379–397 and 486 nm, respectively, and the fluorescence spectra of the PEGPy hydrogel series were recorded in different solvents to explore the coexistence of monomer and excimer emissions.

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Energy Transfer in Dendritic Systems Having Pyrene Peripheral Groups as Donors and Different Acceptor Groups

Cited by 15 publications

References 128 publications

Noncovalent Functionalization of 2D Black Phosphorus with Fluorescent Boronic Derivatives of Pyrene for Probing and Modulating the Interaction with Molecular Oxygen

Noncovalent Functionalization of 2D Black Phosphorus with Fluorescent Boronic Derivatives of Pyrene for Probing and Modulating the Interaction with Molecular Oxygen

Synthesis and Characterization of White-Light Luminescent End-Capped Polyimides Based on FRET and Excited State Intramolecular Proton Transfer

Facile Obtainment of Fluorescent PEG Hydrogels Bearing Pyrene Groups by Frontal Polymerization

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