A new polyfluorene bearing pyridine moieties: a sensitive fluorescent chemosensor for metal ions and cyanide

Lou, Xiaoding; Zhang, Yi; Li, Shuang; Ou, Daxin; Wan, Zhaomin; Qin, Jingui; Li, Zhen

doi:10.1039/c2py20022h

Cited by 40 publications

(16 citation statements)

References 74 publications

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“…[48][49][50][51][52] Thanks to the mild and efficient nature of salicylaldehyde-hydrazine reaction, the morphologies of the preformed self-assemblies remained intact after this post-modification. [48][49][50][51][52] Thanks to the mild and efficient nature of salicylaldehyde-hydrazine reaction, the morphologies of the preformed self-assemblies remained intact after this post-modification.…”

Section: Introductionmentioning

confidence: 99%

Salicylaldehyde-functionalized block copolymer nano-objects: one-pot synthesis via polymerization-induced self-assembly and their simultaneous cross-linking and fluorescence modification

et al. 2016

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Salicylaldehyde-functional diblock copolymer nano-objects were synthesized by polymerization induced self-assembly (PISA) via RAFT dispersion polymerization of a newly designed core-forming monomer, 3-formyl-4-hydroxybenzyl methacrylate (FHMA), using poly(2-hydroxypropyl methacrylate) (PHPMA) macromolecular chain transfer agent as a steric stabilizer in methanol at 65 o C. A range of PHPMA-b-PFHMA block copolymer morphologies including sphere, worm and vesicle could be accessed by adjusting the degree of polymerization of core forming block PFHMA. Since the salicylaldehyde groups of core-forming PFHMA blocks could react with hydrazine in a 2:1 stoichiometry to form salicylaldazines with aggregation-induced emission, one-step post-modification of the PISA nano-objects using hydrazine enabled their inherent nanostructures to be stabilized via covalent cross-linking and simultaneously conferred luminescent features on the resulting stabilized nanoparticles. Solid nano-objects, obtained easily via precipitation into diethyl ether, could be re-dispersed well in methanol and THF. The nano-objects could also be re-dispersed in water to form colloidal dispersions at a low concentration (≤ 1% w/w). Thanks to the stability imparted by the cross-linking, the morphologies of the preformed PISA nano-objects remained intact even after re-dispersing these cross-linked nano-objects in THF (a good solvent for both blocks). The stabilized nano-objects displayed strong orange fluorescence in water, organic solvents or solid states. This work opens the possibility for simultaneous functionlization and stabilization of PISA-generated block copolymer nano-objects. Materials 2-Hydroxypropyl methacrylate (HPMA; J&K, 97%) was passed through a column of basic alumina to remove inhibitor and then stored at -20 °C prior to use. 2, 2′-Azobis(isobutyronitrile) (AIBN; Sinopharm Chemical Reagent, 99%) was purified by recrystallization from ethanol. 4-Cyano-4-(propylthiocarbonothioylthio)pentanoic acid (CPPA) 53 and 5-(chloromethyl)-2-hydroxybenzaldehyde 54 were synthesized according to literature procedures. Other reagents were all analytical grade and used as received. Synthesis of 3-formyl-4-hydroxybenzyl methacrylate (FHMA)A mixture of methacrylic acid (25.8 g, 0.3 mol), sodium hydroxide (12.0 g, 0.3 accelerating voltage of 120 kV. For preparation of TEM samples, a drop of diluted dispersion (0.15 % w/w) solution was deposited onto a carbon-coated copper grid and dried under ambient conditions. All samples were not stained. Results and discussion Synthesis of monomer 3-formyl-4-hydroxybenzyl methacrylate (FHMA)A novel salicylaldehyde functionalized methacrylate monomer FHMA was designed and synthesized readily by the reaction of methacrylic acid with 5-(chloromethyl)-2-hydroxybenzaldehyde (Scheme 1). The structure of FHMA was confirmed on the base of the elemental analysis, MS, and 1 H NMR spectroscopy. The 1 H NMR spectrum (Fig. 1) exhibits the characteristic signals corresponding to methacrylic vinyl (a,b), aldehyde (i) and hydroxyl (h) mo...

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Section: Introductionmentioning

confidence: 99%

Salicylaldehyde-functionalized block copolymer nano-objects: one-pot synthesis via polymerization-induced self-assembly and their simultaneous cross-linking and fluorescence modification

et al. 2016

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“…Li and coworkers employed di(2-picolyl)amine moieties as the receptor group to construct a functional fluorene/carbazole copolymer sensor (CP-11). 30 The three lone pairs on the receptor unit could synergistically bind with Cu 2+ tightly, leading to complete quenching of the fluorescence of the polymer. Alkali and alkaline earth metal ions have no influence on the fluorescence of the polymer due to their poor coordination ability with the receptor units.…”

Section: Mono-pyridine-based Cp Chemosensorsmentioning

confidence: 99%

Fluorescent chemosensors based on conjugated polymers with N-heterocyclic moieties: two decades of progress

et al. 2020

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“…Swager and co-workers have demonstrated that due to facile energy migration, delocalizable, p-electronic conjugated "molecular wire" polymers exhibit pronounced sensitivity enhancement in the fluorescence quenching [2,4]. Many kinds of polymer chemosensors have been designed to defect different analytes, including anions, biomolecules, metal ions and explosives [5][6][7][8][9][10][11]. Typically, the quenching sites are typically generated through the integration of coordination sites, such as bipyridyl (bpy), terpyridyl (tpy) and quinoline groups.…”

Section: Introductionmentioning

confidence: 98%

A new polymer based on dipyridophenazine (dppz) moiety synthesis and sensitive chemosensor toward Cu2+ ion with high selectivity

Zhang

Gong

et al. 2014

Synthetic Metals

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A new polyfluorene bearing pyridine moieties: a sensitive fluorescent chemosensor for metal ions and cyanide

Cited by 40 publications

References 74 publications

Salicylaldehyde-functionalized block copolymer nano-objects: one-pot synthesis via polymerization-induced self-assembly and their simultaneous cross-linking and fluorescence modification

Salicylaldehyde-functionalized block copolymer nano-objects: one-pot synthesis via polymerization-induced self-assembly and their simultaneous cross-linking and fluorescence modification

Fluorescent chemosensors based on conjugated polymers with N-heterocyclic moieties: two decades of progress

A new polymer based on dipyridophenazine (dppz) moiety synthesis and sensitive chemosensor toward Cu2+ ion with high selectivity

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