A New Fullerene Complexation Ligand:  <i>N</i>-Pyridylfulleropyrrolidine

Tat, Fatma; Zhou, Zhiguo; MacMahon, Shaun; Song, Fayi; Rheingold, Arnold L.; Echegoyen, Luís; Schuster, David I.; Wilson, Stephen R.

doi:10.1021/jo049671w

Cited by 69 publications

(51 citation statements)

References 36 publications

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“…Our results also suggest a lack of electronic communication between the pyridyl nitrogen atom and te fullerene cage in N-(4-pyridyl)pyrrolidinofullerene [16] as this compound has almost the same reduction potentials as N-methylpyrrolidinofullerene and our derivative 12, which possesses two 4-pyridyl groups. However, such an electronic communication has been claimed to explain a higher binding constant for complex formation between N-(4-pyridyl)pyrrolidinofullerene and ZnTPP (K a = 7.7 × 10 -4 ) in comparison with the similar complex of 3-methyl-2-(4-pyridyl)pyrrolidinofullerene (K a = 1.4 × 10 -4 ).…”

Section: Electrochemical Properties Of the Synthesized Pyridylappendementioning

confidence: 59%

“…However, such an electronic communication has been claimed to explain a higher binding constant for complex formation between N-(4-pyridyl)pyrrolidinofullerene and ZnTPP (K a = 7.7 × 10 -4 ) in comparison with the similar complex of 3-methyl-2-(4-pyridyl)pyrrolidinofullerene (K a = 1.4 × 10 -4 ). [16] Generally, the electron-withdrawing effect of the fullerene cage on the nitrogen atoms in the addends results in decreased basic properties and lower association constants with ZnTPP, [17] which is inconsistent with the expectation of the authors of ref. [16] …”

Section: Electrochemical Properties Of the Synthesized Pyridylappendementioning

confidence: 88%

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

Troshin

Peregudov

Mühlbacher³

et al. 2005

Eur J Org Chem

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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

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Section: Electrochemical Properties Of the Synthesized Pyridylappendementioning

confidence: 59%

Section: Electrochemical Properties Of the Synthesized Pyridylappendementioning

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

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“…[13] Electrochemical studies further confirmed this effective coupling between the pyridyl nitrogen atom and the fullerene core based on the fact that the first reduction of the C 60 core was shifted by 40 mV upon complexation with a Zn-porphyrin derivative. [14] Thus C 60 hexakis-adducts 2 and 3 with terpyridyl or pyridyl groups in the trans-1 positions and the corresponding trans-1 bis-adducts 4 and 5 (Scheme 3) were selected as the synthetic targets in the present work. Regioselective formation of trans-1 bis-adducts of C 60 has been a challenging task.…”

Section: Introductionmentioning

confidence: 99%

“…After conversion of those potentials versus Ag/Ag + to those versus Fc/Fc + , [33] the values are À1.01 and À1.29 V. The first and second reductions are shifted anodically by 50 and 150 mV, respectively, relative to those of 1 in solution. [14] All peak potentials are proportional to the sweep rate, which was varied between 0.1 and 1 V s À1 , indicating surface-confined behavior due to the immobilization of the electroactive fullerene derivative on the gold surfaces.…”

mentioning

confidence: 99%

Synthesis of Fullerene Adducts with Terpyridyl‐ or Pyridylpyrrolidine Groups in trans‐1 Positions

Zhang

Lukoyanova

Echegoyen

2006

Chemistry A European J

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Two C(60) hexakis-adducts (2 and 3) were synthesized by using a protection-deprotection strategy. The symmetric fullerene tetrakis-adduct 8 was obtained by anthracene removal from the hexakis-adduct 7. Reaction of 8 with terpyridylglycine or pyridylglycine afforded two hexakis-adducts, 2 and 3. By using the retro-cyclopropanation reaction, the four malonate addends located on the equatorial belt of the hexakis-adducts were removed to afford two trans-1 bis-adducts, 4 and 5, with terpyridyl- or pyridylpyrrolidine groups. The structures of 2 and 3 were confirmed by matrix-assisted laser desorption ionization time-of-flight (MALDI-TOF) mass spectrometry, and (1)H, (13)C, and COSY NMR, and UV-visible spectroscopy. The cyclic voltammograms of fullerene multiadducts 2, 3, and 9 show irreversible reductions. Self-assembled monolayers (SAMs) of 1 and 3 were formed on gold surfaces through nitrogen adsorption. SAMs of 3 represent the first example of a fullerene hexakis-adduct formed on gold surfaces through nitrogen adsorption. Controlled potential electrolyses (CPE) were conducted to prepare trans-1 bis-adducts 4 and 5 modified with terpyridyl and pyridyl groups.

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“…Precursor 7 was obtained via synthetic routes according to the literature (59). Porphyrin 2 and fullerene 3 were prepared as described previously (60).…”

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confidence: 99%

Step-by-step self-assembled hybrids that feature control over energy and charge transfer

Grimm

Schornbaum

Jasch

et al. 2012

Proc. Natl. Acad. Sci. U.S.A.

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In the current work, we have documented the use of two complementary supramolecular motifs, namely multipoint hydrogen bonding and metal complexation, as a means to control the stepby-step assembly of a panchromatically absorbing and highly versatile solar energy conversion system. On one hand, two different perylenediimides (1a/1b) have been integrated together with a metalloporphyrin (2) by means of the Hamilton receptor/cyanuric acid hydrogen bonding motif into energy transduction systems 1a•2 or 1b•2. Steady-state and time-resolved measurements corroborated that upon selective photoexcitation of the perylenediimides (1a/1b), an energy transfer evolved from the singlet excited state of the perylenediimides (1a/1b) to that of the metalloporphyrin (2). On the other hand, fullerene (3) and metalloporphyrin (2) form the electron donor-acceptor system 2•3 via axial complexation. Photophysical measurements confirm that an electron transfer prevails from the singlet excited state of 2 to the electron-accepting 3. The correspondingly formed radical ion pair state decays with a lifetime of 1.0 AE 0.1 ns. As a complement to the aforementioned, the energy transduction features of 1a•2 were combined with the electron donor-acceptor characteristics of 2•3 to afford 1a•2•3. To this end, time-resolved measurements reveal that the initially occurring energy-transfer interaction (53 AE 3 ps) between 1a/1b and 2 is followed by an electron transfer (12 AE 1 ps) from 2 to 3. From multiwavelength analyses, the lifetime of the radical ion pair state in 1a•2•3-as a product of a cascade of light-induced energy and electron transfer-was derived as 3.8 AE 0.2 ns. I n recent years, the conversion of solar energy into electrical energy has been one of the most important areas of scientific research due to the constantly growing human energy demands (1, 2). In order to design efficient, low-cost, environmentally responsible artificial photosynthetic systems, research follows the concepts of nature (3, 4). Similar to natural photosynthetic organisms (5-8), artificial systems undergo cascades of light-induced energy and electron transfer reactions. The absorbed energy is converted into chemical potential energy in the form of a radical ion pair state (9). These events take place in organized arrays of photofunctional chromophores within specifically tailored environments that allow an efficient light harvesting. As an important prerequisite, the lifetime of the excited states should be long enough to power efficient electron transfer in order to obtain radical ion pair states. Therefore, the development of panchromatically absorbing molecules with appropriate absorptive properties for light harvesting is desirable.Owing to their biological relevance and favorable properties as natural chromophores, porphyrinoids are widely used as molecular components in artificial photosynthetic systems. Their functions include panchromatic light harvesting through most of the visible part of the solar spectrum and electron transport (10-26). As another m...

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A New Fullerene Complexation Ligand: N-Pyridylfulleropyrrolidine

Cited by 69 publications

References 36 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

Synthesis of Fullerene Adducts with Terpyridyl‐ or Pyridylpyrrolidine Groups in trans‐1 Positions

Step-by-step self-assembled hybrids that feature control over energy and charge transfer

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