Donor–acceptor interaction of fullerene C60 with triptycene in molecular complex TPC·C60

Konarev, Dmitri V.; Drichko, Natalia; Lyubovskaya, Rimma N.; Shul’ga, Yu. M.; Litvinov, Alexey L.; Semkin, V. N.; Dubitsky, Y.; Zaopo, A.

doi:10.1016/s0022-2860(00)00406-3

Cited by 28 publications

(46 citation statements)

References 16 publications

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“…C 60 and a fivefold molar excess of the corresponding M(Et 2 dtc) x were dissolved in benzonitrile at 60°C over 2 h, the solutions were cooled down, filtered off, and the spectra of the resulting solutions were measured in anaerobic conditions in the 600-1600 nm range. Cu I , Co II , and V II diethyldithiocarbamates reduce C 60 to a radical anion, and an absorption band characteristic of C 60 -is manifested at 1070 nm.…”

Section: Interaction Of Fullerenes With Metal(ii) Diethyldithiocarbammentioning

confidence: 99%

“…Cu I , Co II , and V II diethyldithiocarbamates reduce C 60 to a radical anion, and an absorption band characteristic of C 60 -is manifested at 1070 nm. On the contrary, Mn(Et 2 dtc) 2 cannot reduce C 60 .…”

Section: Interaction Of Fullerenes With Metal(ii) Diethyldithiocarbammentioning

confidence: 99%

“…[22] In contrast to dimeric Cu(dedtc) 2 , M(Bnz 2 dtc) 2 are monomers with planar conformation of the central (NCS 2 ) 2 M fragment, which is charac-teristic of Ni II , Pd II , and Pt II dithiocarbamates. [23][24][25][26][27] Moreover, Pd(Bnz 2 dtc) 2 forms a multi-component ionic complex containing C 60 with a relatively large hysteresis and the decrease of the dimerization temperature at a fast cooling rate. [22] Thus, metal dialkyldithiocarbamates, M(R 2 dtc) x , can successfully be used in the design of molecular and ionic complexes with fullerenes.…”

Section: Introductionmentioning

confidence: 99%

“…M(R 2 dtc) x were both weak and strong donors. The interaction of C 60 2 and Cd(Et 2 dtc) 2 was studied upon illumination with white light. The comparison of the photoconductivity and the absorption spectra allows one to suggest the mechanisms of free charge carrier generation.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Crystal Structures, Magnetic Properties and Photoconductivity of C₆₀ and C₇₀ Complexes with Metal Dialkyldithiocarbamates M(R₂dtc)_x, where M = Cu^II, Cu^I, Ag^I, Zn^II, Cd^II, Hg^II, Mn^II, Ni^II, and Pt^II; R = Me, Et, and nPr

et al. 2006

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efficiently cocrystallized with fullerene molecules as tetrahedral monomers (6, 12), dimers (1, 7, 11), and tetramers (3, 4). Fullerene molecules form closely packed hexagonal and square layers in 1, 7, and 11, hexagonal and tetragonal 3D structures in 6 and 12, and island motifs in 3 and 4. Complexes 1-15 have a neutral ground state. However, the formation of the complexes with fullerenes changes the environment of paramagnetic Cu II and Mn II. The EPR spectra of 1, 2, 11, and 13 are essentially modified relative to those of pristine Cu(R 2 dtc) 2 because of a weak coordination of Cu II to fullerene

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Section: Interaction Of Fullerenes With Metal(ii) Diethyldithiocarbammentioning

confidence: 99%

Section: Interaction Of Fullerenes With Metal(ii) Diethyldithiocarbammentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis, Crystal Structures, Magnetic Properties and Photoconductivity of C₆₀ and C₇₀ Complexes with Metal Dialkyldithiocarbamates M(R₂dtc)_x, where M = Cu^II, Cu^I, Ag^I, Zn^II, Cd^II, Hg^II, Mn^II, Ni^II, and Pt^II; R = Me, Et, and nPr

et al. 2006

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“…Despite the insolubility of fullerene in bulk water, a single molecule of fullerene has considerable affinity for water molecules because of hydrogen bonding (14), and this may account for the present observation. The change of the permeability and thermodynamics at Ϸ45°C is possibly due to the change in the molecular packing, as observed in fullerene crystals (15,16), because temperature variation from 10°C to 80°C did not much change the size of the vesicles.…”

Section: Resultsmentioning

confidence: 87%

Energetics of water permeation through fullerene membrane

Isobe

Homma

Nakamura

2007

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

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Lipid bilayer membranes are important as fundamental structures in biology and possess characteristic water-permeability, stability, and mechanical properties. Water permeation through a lipid bilayer membrane occurs readily, and more readily at higher temperature, which is largely due to an enthalpy cost of the liquid-to-gas phase transition of water. A fullerene bilayer membrane formed by dissolution of a water-soluble fullerene, Ph 5C60K, has now been shown to possess properties entirely different from those of the lipid membranes. The fullerene membrane is several orders of magnitude less permeable to water than a lipid membrane, and the permeability decreases at higher temperature. Water permeation is burdened by a very large entropy loss and may be favored slightly by an enthalpy gain, which is contrary to the energetics observed for the lipid membrane. We ascribe this energetics to favorable interactions of water molecules to the surface of the fullerene molecules as they pass through the clefts of the rigid fullerene bilayer. The findings provide possibilities of membrane design in science and technology.bilayer membrane ͉ vesicle ͉ entropy barrier V esicles made of a lipid bilayer membrane such as a cell membrane are fundamental structures in biology. The membrane maintains stability and mechanical properties to sustain the integrity of the biological machinery while allowing water to permeate through the liquid crystalline film of the hydrocarbon chains (1). The low energy barrier for water permeation is largely due to the small enthalpy cost of the liquid-to-gas phase transition of water (2). The lipid membrane and its water permeation mechanism have long served as important models for design and analysis of membrane structures. We have reported that, upon dissolution in water, water-soluble fullerene (Ph 5 C 60 K) ( Fig. 1) (3) produces spherical bilayer vesicles (Ϸ15-nm radius) [see supporting information (SI) Fig. 7] as an exclusive self-assembly object (4, 5). We report here that the vesicles made from water-soluble fullerene molecules show water-permeability, stability, and mechanical characteristics entirely different from those of the conventional vesicles. The fullerene membrane is several orders of magnitude less permeable to water than a lipid membrane (2, 6, 7), and the permeability decreases at higher temperature. The high energy barrier for permeation is due to a very large negative activation entropy. We suggest that water molecules lose their mobility in the clefts of the rigid fullerene bilayer, just as in hydration of crystalline proteins or metal salts. Results and DiscussionA solution study of the thermodynamics of water permeation through the fullerene membrane revealed that the mechanism of permeation is very different from that so far known for lipid bilayers. The vesicles were found to be quite tough on a mica surface, as examined by atomic force microscopy (4). In contrast to lipid vesicles, the fullerene vesicles show neither 1 H nor 13 C NMR signals in water (at 10 -80°C), an...

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Synthesis of n‐type [60]Fullerene Derivatives with Sterically Bulky tert‐Butyl Groups for Vacuum Deposition Processes

Shibuya

Choi

et al. 2022

Chemistry An Asian Journal

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[60]Fullerene derivatives with high thermal stability can be used for vacuum deposition under heating to fabricate thin films for organic electronic devices. Here, we investigated the thermal stability of [60]fullerene derivatives with various bulky substituents for thermal evaporation under vacuum by means of thermogravimetric analysis under reduced and normal pressure. We found sterically bulky groups such as tert‐butyl groups of [60]fullerene derivatives lowered the vacuum deposition temperature. Also, we performed isothermal thermogravimetric analysis to examine the long‐term thermal stability of the designed compounds under heating conditions. Furthermore, we investigated the UV‐Vis absorption patterns of the deposited films. Absorption in the blue wavelength range, which was attributed to intermolecular HOMO–LUMO transitions among the molecular orbitals of adjacent [60]fullerenes, was dramatically modified. These results were associated with the prevention of aggregation among neighboring [60]fullerene by the sterically bulky groups. This concept could contribute to expanding the use of evaporable [60]fullerene derivatives in organic thin‐film electronics research fields.

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Donor–acceptor interaction of fullerene C60 with triptycene in molecular complex TPC·C60

Cited by 28 publications

References 16 publications

Synthesis, Crystal Structures, Magnetic Properties and Photoconductivity of C₆₀ and C₇₀ Complexes with Metal Dialkyldithiocarbamates M(R₂dtc)_x, where M = Cu^II, Cu^I, Ag^I, Zn^II, Cd^II, Hg^II, Mn^II, Ni^II, and Pt^II; R = Me, Et, and nPr

Synthesis, Crystal Structures, Magnetic Properties and Photoconductivity of C₆₀ and C₇₀ Complexes with Metal Dialkyldithiocarbamates M(R₂dtc)_x, where M = Cu^II, Cu^I, Ag^I, Zn^II, Cd^II, Hg^II, Mn^II, Ni^II, and Pt^II; R = Me, Et, and nPr

Energetics of water permeation through fullerene membrane

Synthesis of n‐type [60]Fullerene Derivatives with Sterically Bulky tert‐Butyl Groups for Vacuum Deposition Processes

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Donor–acceptor interaction of fullerene C60 with triptycene in molecular complex TPC·C60

Cited by 28 publications

References 16 publications

Synthesis, Crystal Structures, Magnetic Properties and Photoconductivity of C60 and C70 Complexes with Metal Dialkyldithiocarbamates M(R2dtc)x, where M = CuII, CuI, AgI, ZnII, CdII, HgII, MnII, NiII, and PtII; R = Me, Et, and nPr

Synthesis, Crystal Structures, Magnetic Properties and Photoconductivity of C60 and C70 Complexes with Metal Dialkyldithiocarbamates M(R2dtc)x, where M = CuII, CuI, AgI, ZnII, CdII, HgII, MnII, NiII, and PtII; R = Me, Et, and nPr

Energetics of water permeation through fullerene membrane

Synthesis of n‐type [60]Fullerene Derivatives with Sterically Bulky tert‐Butyl Groups for Vacuum Deposition Processes

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Synthesis, Crystal Structures, Magnetic Properties and Photoconductivity of C₆₀ and C₇₀ Complexes with Metal Dialkyldithiocarbamates M(R₂dtc)_x, where M = Cu^II, Cu^I, Ag^I, Zn^II, Cd^II, Hg^II, Mn^II, Ni^II, and Pt^II; R = Me, Et, and nPr

Synthesis, Crystal Structures, Magnetic Properties and Photoconductivity of C₆₀ and C₇₀ Complexes with Metal Dialkyldithiocarbamates M(R₂dtc)_x, where M = Cu^II, Cu^I, Ag^I, Zn^II, Cd^II, Hg^II, Mn^II, Ni^II, and Pt^II; R = Me, Et, and nPr