Synthesis of Pyrrolidine Ring-Fused Fullerene Multicarboxylates by Photoreaction

Gan, Liangbing; Jiang, Jianfeng; Zhang, Wen; Su, Yang; Shi, Yaru; Huang, Chunhui; Pan, Jiali; Lu, Miao; Wu, Yi

doi:10.1021/jo971990i

Cited by 89 publications

(55 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In the case of the trans isomer, the signal is shifted about 0.6 ppm to lower field than the cis isomer; a similar difference was reported previously for the cis and trans isomers of 3Ј,5Ј-di(2-methoxycarbonyl)pyrrolidinofullerene. [9] Thus, cis and trans isomers of 3Ј,5Ј-disubstituted pyrrolidinofullerenes can be distinguished by their 1 H NMR spectra; the cis arrangement of the substituents in 1, 3, and 4 was proved similarly.…”

Section: -Picolylamine and N-substituted 2-picolylamines As Substratesmentioning

confidence: 88%

An Efficient [2+3] Cycloaddition Approach to the Synthesis of Pyridyl‐Appended Fullerene Ligands

Troshin

Peregudov

Mühlbacher³

et al. 2005

Eur J Org Chem

View full text Add to dashboard Cite

We have used 2-, 3-, and 4-picolylamines and their various N-substituted derivatives as substrates to generate azomethine ylides for [2+3] cycloaddition to [60]fullerene. A considerable difference in the reactivity of isomeric picolylamines was observed; however, even less reactive 3-picolylamines afford high yields of products under acid or base catalysis. This method provides easy access to a large family of valuable ligands (pyridyl-substituted pyrrolidinofullerenes) that can be used in the design of transition-metal complexes

show abstract

Section: -Picolylamine and N-substituted 2-picolylamines As Substratesmentioning

confidence: 88%

An Efficient [2+3] Cycloaddition Approach to the Synthesis of Pyridyl‐Appended Fullerene Ligands

Troshin

Peregudov

Mühlbacher³

et al. 2005

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

“…The mechanism, similar to the reaction pathway of the amino acid ester (Scheme 17), involves the formation of the carboxyl radical (67). Decarboxylation of (67) forms the aminomethyl radical (69) which undergoes addition to [60]fullerene and Habstraction from the environment to yield (70).…”

Section: Radical Additionsmentioning

confidence: 99%

“…Fulleroproline derivatives can be formed by photolysis of primary and secondary amino acid esters (Scheme 16) [65][66][67] . The initial key step in these photoreactions is presumed to be the formation of an carbon-centred radical (64) which attacks the fullerene (Scheme 17).…”

Section: Radical Additionsmentioning

confidence: 99%

[60]Fullerene Amino Acids and Related Derivatives

Burley¹,

Keller²,

Pyne³

1999

Fullerene Science and Technology

View full text Add to dashboard Cite

show abstract

“…The synthesis of C 60 EM is described elsewhere [25] and that of C 60 EA will be published separately.…”

Section: Methodsmentioning

confidence: 99%

Cyclic Voltammetry Study of the C60-EDTA Derivative Films

Luo

Li²,

Zhang

et al. 1999

Electroanalysis

Self Cite

View full text Add to dashboard Cite

The ®lms of an amphiphilic C 60 -EDTA (C 60 EA) and its tetramethyl ester (C 60 EM), prepared both by drop-coating and Langmuir-Blodgett (LB) technique, were studied by cyclic voltammetry in acetonitrile solutions of tetra-n-butylammonium hexa¯uorophosphate as the supporting electrolyte. The drop-coated ®lm of C 60 EM displayed four pairs of redox peaks, which vanished after a few cycles due to the ®lm dissolution. For the LB ®lm of C 60 EM, three irreversible reduction peaks were observed. Both the drop-coated and the LB ®lm of C 60 EA showed two irreversible reduction peaks.Keywords: C 60 -EDTA derivatives, Langmuir±Blodgett and drop-coated ®lms, Cyclic voltammetry Because of their unique molecular structure and peculiar physical and chemical properties, fullerenes and their derivatives attracted an unprecedented worldwide research effort. Thin ®lms of [60]fullerene, C 60 , and its derivatives have been widely investigated for structural characterization, interfacial electron transfer, and ion transport [1]. Electrochemical reduction of a fullerene ®lm is of interest because it provides a straightforward and accurate means to control the redox state of the material, e. g., in studies of the ®lm conductivity.A Langmuir-Blodgett technique is one of the most widely adopted approaches to prepare structurally ordered fullerene thin ®lms at the air-water interface and subsequent transfer of these ®lms onto a solid substrate. Initially, Bard et al. reported successful preparation of a C 60 Langmuir ®lm of a limiting molecular area of 98 A Ê 2 [2]. They also reported on electrochemical behavior of the C 60 LB ®lm afterward [3]. At the air-water interface pristine C 60 forms ill-de®ned ®lm of three-dimensional aggregates rather than a monolayer ®lm [4]. In order to prevent the aggregation of C 60 in such a ®lm, different amphiphilic fullerene derivatives have been prepared [5±21]. In these derivatives, hydrophilic headgroups are attached to a lipophilic fullerene core for enhanced interactions with the water subphase.Bryce and Petty reported [5] on formation of stable Langmuir mono-and multilayer ®lms of a t-butyl derivatized fullerene, but only the multilayer ®lms could be transferred onto solid substrates. Their cyclic voltammetry curves studies exhibited reversible peaks for the ®rst three redox processes of a LB ®lm [6].In the present paper, we report on the cyclic voltammetry behavior of the LB ®lms of an amphiphilic C 60 -EDTA (C 60 EA) and its tetramethyl ester (C 60 EM) (see Scheme 1), and compared this behavior with that of their drop-coated ®lms.Cyclic voltammetry behavior of the drop-coated ®lm: Figure 1 shows CV curves for the drop-coated ®lm of C 60 EM in MeCN containing Bu 4 NPF 6 as the supporting electrolyte. Four pairs of redox peaks were observed. The reoxidation charge was signi®cantly smaller than the reduction charge, indicating irreversible ®lm damage due to either its dissolution or chemical deactivation. In the second cycle, the peak currents were much smaller than in the ®rst one, especi...

show abstract

Synthesis of Pyrrolidine Ring-Fused Fullerene Multicarboxylates by Photoreaction

Cited by 89 publications

References 33 publications

An Efficient [2+3] Cycloaddition Approach to the Synthesis of Pyridyl‐Appended Fullerene Ligands

An Efficient [2+3] Cycloaddition Approach to the Synthesis of Pyridyl‐Appended Fullerene Ligands

[60]Fullerene Amino Acids and Related Derivatives

Cyclic Voltammetry Study of the C60-EDTA Derivative Films

Contact Info

Product

Resources

About