Pyrene and anthracene dicarboxylic acids as fluorescent brightening comonomers for polyester

Connor, Daniel M.; Kriegel, Robert M.; Collard, David M.; Liotta, Charles L.; Schiraldi, David A.

doi:10.1002/(sici)1099-0518(20000415)38:8<1291::aid-pola13>3.0.co;2-1

Cited by 18 publications

(4 citation statements)

References 22 publications

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Section: Introductionmentioning

confidence: 99%

“…Fluorescent polymers (FPs) that can emit fluorescence under the irradiation of ultraviolet light (UV) have attracted considerable attention in the past decades due to their extensive applications in sensors, − bioimaging, − display, data storage, , decoration, polymer characterizations, − etc. So far, diverse strategies for producing FPs have been reported in the literature. − One of them is based on the aggregation-induced-emission (AIE) mechanism that was first found by Tang and co-workers . It has been demonstrated that some conjugate molecules with a nonplanar structure, e.g., tetraphenylethylene (TPE), exhibit weak fluorescence in dilute solution but can emit strong fluorescence in the aggregate state as a result of suppressed intra- and intermolecular movements .…”

Section: Introductionmentioning

confidence: 99%

“…The other frequently reported strategy for preparing FPs is to synthesize various polymers bearing pyrene ,,, or its derivatives. , These planar aromatic units can emit strong fluorescence in dilute solution but often suffer from the aggregation-caused quenching (ACQ) effects due to the formation of sandwich-shaped excimers or exciplexes while in a high concentration or aggregate state . One of the effective methods for restraining the ACQ effects is to connect these aromatic units with a polymer backbone by covalent approaches.…”

Section: Introductionmentioning

confidence: 99%

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A Universal Strategy for Producing Fluorescent Polymers Based on Designer Hyperbranched Polyethylene Ternary Copolymers

Song

et al. 2022

Macromolecules

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We herein demonstrate a universal strategy for producing fluorescent polymers (FPs) from conventional resins by adding designer hyperbranched polyethylene (HBPE) copolymers based on the aggregationenhanced excimer emission effect. As an example, a copolymer, HBPE@Py@ PGMA, that possesses an HBPE backbone simultaneously bearing pyrene terminal groups and poly(glycidyl methacrylate) (PGMA) side chains has been synthesized by combining Pd-diimine-catalyzed chain walking ethylene copolymerization and atomic transfer radical polymerization techniques, and epoxy resin-based composites have been obtained by physically mixing with the copolymer. It is found that while the PGMA side chains make the copolymer well dispersible in the epoxy resin matrix, the HBPE backbone can effectively promote the formation of intra/intermolecular pyrene excimers, thus rendering epoxy resin that can emit homogeneous and strong fluorescence even at extremely low pyrene concentrations (0.05−0.20 wt %). Representatively, other FPs also have been successfully prepared from the ethylene-vinyl acetate copolymer, poly(methyl methacrylate), and polystyrene by following this strategy.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A Universal Strategy for Producing Fluorescent Polymers Based on Designer Hyperbranched Polyethylene Ternary Copolymers

Song

et al. 2022

Macromolecules

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“…[4] From the perspective of the photosensitivity characteristics, polymers bearing highly sensitive fluorophores to external stimulus continue to be explored not only for their optical properties, but also for particular applications as chemosensing, optical switching and molecular computation, and so on. [5,6] One of the most used fluorophore is pyrene and its derivatives, which has a high fluorescence emission quantum yield and a rather long excited state lifetime. However, some effort has been made to synthesize pyrene-labeled polymers, [7][8][9][10] amphiphilic copolymers, [11][12][13] and polyelectrolytes [14][15][16] to name some examples, in order to study the structure, optical sensor ability, conformational properties, aggregates formation, or polymer micellization.…”

Section: Introductionmentioning

confidence: 99%

Preparation and characterization of novel p-acryloyloxybenzaldehyde copolymers bearing pyrene or fluorescein moieties. Interaction of fluorophore with some quenchers and silver nanoparticles

Buruiana¹,

Podasca²,

Buruiană³

2013

Designed Monomers and Polymers

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Two photopolymers, poly(vinyl acetate-co-p-acryloyloxybenzilideneiminepyrene) poly(VAc-co-AcrBzA)-Py and poly (vinyl acetate-co-p-acryloyloxybenzilideniminefluorescein) poly(VAc-co-AcrBzA)-Fl with pyrene and fluorescein in structure, have been prepared by chemical modification of the parent copolymer prior obtained through classical radical copolymerization. The structures of the polymers were characterized by FTIR, 1 H ( 13 C) NMR, UV, differential scanning calorimetry and thermogravimetric analysis, and gel permeation chromatography. The fluorescence properties of the photopolymers were investigated in dimethylformamide solutions containing various quenching agents (nitrobenzene, nitrophenol, p-nitrotoluene, picric acid, tetracyanoquinodimethane, Co 2+ , Hg 2+ , [UO 2 ] 2+ , NaOH, and HCl), the quenching efficiency varying in the next order: picric acid > TCNQ > p-nitrotoluene > nitrophenol. Quenching the fluorescence of fluoresceinimine occured only in acid medium (pH: 7.3-2.5) due to the protonated nitrogen, whereas with increasing basic pH (pH: 7.3-9.7) the fluorescence increased. Besides, fluorescence quenching or enhancement of fluorescence by silver nanoparticles (NPs) in situ photogenerated was investigated, our observations suggesting the role of polymer structure in stabilizing metal NPs in thin films.

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Development of Pyrene Derivatives as Promising n‐Type Semiconductors: Synthesis, Structural and Spectral Properties

et al. 2017

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A series of promising candidates for n‐type semiconductors, which were based on a 1,6‐, 1,8‐ and mono‐substituted pyrene‐thiophene backbone with a cyano group and dicyanovinylene moieties, were synthesized. The compounds were characterized using NMR spectroscopy, elemental analysis, UV‐vis, photoluminescence (PL), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), cyclic voltametry (CV) and DFT calculations. The substituent effects on molecular properties were studied in detail. It was found that the dicyanovinylene substitution enhanced the coplanarity of the π‐conjugated systems as compared to cyano substitution. The LUMO energy level was located deeply, and one of them had LUMO of below −4.00 eV, indicating that they may be promising candidates for n‐type semiconductors.

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Pyrene and anthracene dicarboxylic acids as fluorescent brightening comonomers for polyester

Cited by 18 publications

References 22 publications

A Universal Strategy for Producing Fluorescent Polymers Based on Designer Hyperbranched Polyethylene Ternary Copolymers

A Universal Strategy for Producing Fluorescent Polymers Based on Designer Hyperbranched Polyethylene Ternary Copolymers

Preparation and characterization of novel p-acryloyloxybenzaldehyde copolymers bearing pyrene or fluorescein moieties. Interaction of fluorophore with some quenchers and silver nanoparticles

Development of Pyrene Derivatives as Promising n‐Type Semiconductors: Synthesis, Structural and Spectral Properties

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