Improved synthesis of fullerynes by Fisher esterification for modular and efficient construction of fullerene polymers with high fullerene functionality

Zhang, Wenbin; He, Jinlin; Dong, Xue‐Hui; Wang, Chien‐Lung; Li, Hui; Teng, Fu-Ai; Li, Xiaopeng; Wesdemiotis, Chrys; Quirk, Roderic P.; Cheng, Stephen Z. D.

doi:10.1016/j.polymer.2011.07.026

Cited by 21 publications

(20 citation statements)

References 44 publications

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“…A high molecular weight shoulder peak was observed in both fullerene polymers. The shoulder may be caused by the aggregation of C 60 in THF,[ 11,13,50 ] as the fullerene polymers were well defined without multi-addition product evidenced form the high sensitive MALDI-TOF. The shoulder peak of C 60 -2PS is smaller than that of C 60 -1PS indicating the tendency of aggregation in C 60 -2PS is weaker.…”

Section: Resultsmentioning

confidence: 99%

“…[ 24–28 ] However, the syntheses of fullerynes are usually nontrivial. [ 5 ] Several methods have been reported,[ 11,29–32 ] but most of them involves multi-step syntheses and drastic reaction conditions. In order for the ‘click’ chemistry to be viable for practical applications, it is important to find that fullerynes are readily available and highly reactive.…”

Section: Introductionmentioning

confidence: 99%

“…In order for the ‘click’ chemistry to be viable for practical applications, it is important to find that fullerynes are readily available and highly reactive. [ 11 ] Bingel–Hirsch reaction has been considered as one of the most versatile and efficient methods for C 60 functionalization under mild reaction conditions to afford stable methanofullerene products with high yields. [ 33–35 ] Nierengarten et al [ 36–46 ] prepared C 60 derivatives bearing terminal alkyne, and used them as building blocks in the efficient preparation of ‘sugar balls’ and other conjugates.…”

Section: Introductionmentioning

confidence: 99%

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Convenient syntheses of fullerynes for ‘clicking’ into fullerene polymers

Teng

Guo

et al. 2016

Designed Monomers and Polymers

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Alkyne-functionalized fullerenes (fullerynes) were designed and conveniently synthesized via Bingel reaction in one step with high yields. They were used to react with azido-functionalized polystyrene (PS) via Huisgen [3 + 2] cycloaddition ‘click’ chemistry to form two fullerene polymers: one with C60 tethered to the end of a PS chain (C60-1PS) and the other with C60 tethered at the junction point of two PS chains of identical molecular weight (C60-2PS). The fullerene polymers were characterized by 1H NMR, 13C NMR, FT-IR, MALDI-TOF mass spectrometry and SEC. The results showed that the fullerene polymers are well-defined with narrow polydispersity and high fullerene functionality. Besides, aggregation of C60 in THF was observed in the SEC traces. The optical properties of the fullerene polymers were studied by UV–Vis absorption spectroscopy, and the results suggested that the PS chain(s) on the fullerene core has no remarkable effect on the optic property of C60. The thermal properties of the fullerene polymers were studied by TGA and DSC, and the results indicated that the two fullerene polymers with different C60 content and distinct molecular topology may have different self-assemble architectures in the solid state. The well-defined fullerene polymers can be used as model compounds to study the self-assemble architecture of shape amphiphiles based on polymer-tethered molecular nanoparticles.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Convenient syntheses of fullerynes for ‘clicking’ into fullerene polymers

Teng

Guo

et al. 2016

Designed Monomers and Polymers

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“…In some cases the nanomaterial can be made and used directly as an LC support . Although the situations in which this method can be used are limited, such an approach could potentially result in a large amount of the nanomaterial being placed into a system, leading to high retention .…”

Section: Incorporation or Immobilization Of Nanomaterials In Lc Systemsmentioning

confidence: 99%

Nanomaterials as stationary phases and supports in liquid chromatography

et al. 2017

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The development of various nanomaterials over the last few decades has led to many applications for these materials in liquid chromatography (LC). This review will look at the types of nanomaterials that have been incorporated into LC systems and the applications that have been explored for such systems. A number of carbon-based nanomaterials and inorganic nanomaterials have been considered for use in LC, ranging from carbon nanotubes, fullerenes and nanodiamonds to metal nanoparticles and nanostructures based on silica, alumina, zirconia and titanium dioxide. Many ways have been described for incorporating these nanomaterials into LC systems. These methods have included covalent immobilization, adsorption, entrapment, and the synthesis or direct development of nanomaterials as part of a chromatographic support. Nanomaterials have been used in many types of LC. These applications have included the reversed-phase, normal-phase, ion-exchange, and affinity modes of LC, as well as related methods such as chiral separations, ion-pair chromatography and hydrophilic interaction liquid chromatography. Both small and large analytes (e.g., dyes, drugs, amino acids, peptides and proteins) have been used to evaluate possible applications for these nanomaterial-based methods. The use of nanomaterials in columns, capillaries and planar chromatography has been considered as part of these efforts. Potential advantages of nanomaterials in these applications have included their good chemical and physical stabilities, the variety of interactions many nanomaterials can have with analytes, and their unique retention properties in some separation formats.

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“…[16] Pyridine-appended chlorophyll derivative 19 was synthesized in three steps from methyl pyropheophorbide-a (11; Scheme 3), which was obtained by following ap reviously reported procedure. [17] The vinyl group in 11 was oxidized to the formyl group by Lemieux-Johnson oxidation with OsO 4 and NaIO 4 to give methylp yropheophorbide -d (12).…”

Section: Synthesesmentioning

confidence: 99%

Cyclic Tetramers of Zinc Chlorophylls as a Coupled Light‐Harvesting Antenna–Charge‐Separation System

Shinozaki

Ohkubo

Fukuzumi

et al. 2015

Chemistry A European J

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A coupled light-harvesting antenna-charge-separation system, consisting of self-assembled zinc chlorophyll derivatives that incorporate an electron-accepting unit, is reported. The cyclic tetramers that incorporated an electron acceptor were constructed by the co-assembly of a pyridine-appended zinc chlorophyll derivative, ZnPy, and a zinc chlorophyll derivative further decorated with a fullerene unit, ZnPyC60 . Comprehensive steady-state and time-resolved spectroscopic studies were conducted for the individual tetramers of ZnPy and ZnPyC60 as well as their co-tetramers. Intra-assembly singlet energy transfer was confirmed by singlet-singlet annihilation in the ZnPy tetramer. Electron transfer from the singlet chlorin unit to the fullerene unit was clearly demonstrated by the transient absorption of the fullerene radical anion in the ZnPyC60 tetramer. Finally, with the co-tetramer, a coupled light-harvesting and charge-separation system with practically 100 % quantum efficiency was demonstrated.

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Improved synthesis of fullerynes by Fisher esterification for modular and efficient construction of fullerene polymers with high fullerene functionality

Cited by 21 publications

References 44 publications

Convenient syntheses of fullerynes for ‘clicking’ into fullerene polymers

Convenient syntheses of fullerynes for ‘clicking’ into fullerene polymers

Nanomaterials as stationary phases and supports in liquid chromatography

Cyclic Tetramers of Zinc Chlorophylls as a Coupled Light‐Harvesting Antenna–Charge‐Separation System

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