Solution processable C60 fullerene-hydrazone dyads for optoelectronics

Urnikaite, Simona; Malinauskas, Tadas; Gaidelis, Valentas; Maldžius, Robertas; Jankauskas, Vygintas; Getautis, Vytautas

doi:10.1016/j.carbon.2010.09.030

Cited by 12 publications

(8 citation statements)

References 41 publications

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“…The peak at 233 nm is the n → π* absorption peak of −ONO 2 , whereas those at 257 and 325 nm are the skeleton absorption peaks of the C 60 cage. Meanwhile, the peak at 427 nm is a characteristic absorption peak of [6,6]fullerene monoadduct derivative, 30,31 which shows that PGN is successfully grafted to the C 60 cage through the [6,6]monoaddition of C 60 and BM-PGN 5.…”

Section: Methodsmentioning

confidence: 97%

Synthesis and Characterization of [60]Fullerene-Poly(glycidyl nitrate) and Its Thermal Decomposition

Gong

Jin

Peng

et al. 2015

Ind. Eng. Chem. Res.

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A new energetic fullerene derivative [60]fullerene-poly(glycidyl nitrate) (C60-PGN) was synthesized through a modified Bingel reaction of C60 and bromomalonic acid PGN ester in the presence of amino acid and dimethyl sulfoxide. The obtained product was characterized by nuclear magnetic resonance, Fourier transform infrared spectroscopy, and ultraviolet–visible spectroscopy. Results confirmed that C60-PGN was synthesized successfully. The thermal decomposition analysis of C60-PGN was investigated by differential scanning calorimetry and thermogravimetric analysis with infrared spectroscopy, which revealed that C60-PGN exhibits good resistance to thermal decomposition up to 200 °C. The kinetic parameters of the thermal decomposition of C60-PGN were also obtained from the differential thermal analysis data by Kissinger and Ozawa–Doyle methods, with E a = 170.85 and 168.29 kJ·mol–1, respectively. C60-PGN exhibits stability higher than that of any other known polynitrofullerenes.

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Section: Methodsmentioning

confidence: 97%

Synthesis and Characterization of [60]Fullerene-Poly(glycidyl nitrate) and Its Thermal Decomposition

Gong

Jin

Peng

et al. 2015

Ind. Eng. Chem. Res.

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“…Multiple double bonds are available on the carbon backbone, making multiple functionalization an interesting route towards new functional materials. This has led to a variety of novel compounds with finely tunable features that have found applications as catalysts and antioxidants, as well as in sensors and solar cells . The functionalization of fullerenes does not only modify their properties, but converts them into more processable forms, as pristine C 60 is only sparsely soluble in most solvents, making it intractable.…”

Section: Methodsmentioning

confidence: 99%

Novel 5‐(Benzo[b]thiophen‐3‐yl)pyridine‐3‐carbaldehyde (BTPA) Functionalization Framework For Modulating Fullerene Electronics

et al. 2017

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Through ac ycloaddition reaction, fullerene( C 60 )w as derivatized with an ovel organic compound 5-(benzo [b]thiophen-3-yl)pyridine-3-carbaldehyde to form the processable and stable 3-(benzo [b]thiophene-3yl)-5-fullero-1-methylpyrrolidinepyridine (BTFP) compound. BTFP exhibits close similarities to phenyl-C61-butyric-acid-methyl-ester (PCBM)i nt erms of first reduction potentialv alues (À0.62 and À0.61 Vv s. Ag/AgCl, for BTFP and PCBM, respectively)a nd lowest occupied molecular orbital (LUMO) energy level values (3.93 eV in both cases). In chloroform, BTFP exhibits ab athochromic shift in the l max of BTFP (l max, BTFP = 290 nm and l max, PCBM = 260 nm), owing to the graftedb enzo [b]thiophene-3-yl)pyridinem oiety.D espite the similarityi nL UMO (3.93 eV) energy values, BTFP and PCBM differ in their luminescence-quenching ability.T he bathochromic shift in the l max of BTFP (relative to PCMB) is likely to contribute to improved light absorption of as uitable donor for photovoltaic applications.The uniquenesso fc losed-cage, nearly spherical C 60 and related fullerenem olecules has attracted considerable attention. The icosahedrals ymmetry [1] and numerousp ossibilities of functionalizationa llow the modulation of their optoelectronic properties, [2] leading to unabated interest in these intriguing carbon allotropes. The chemistry of fullerenes is that of electron-poor olefins, with sp 2 carbon atoms constrained into apyramidalized geometry.M ultiple double bonds are available on the carbon backbone, making multiple functionalization [3] an interesting route towards new functional materials.This has led to avariety of novel compoundsw ithf inely tunable features thath ave found applicationsa sc atalysts [4] and antioxidants, [5] as well as in sensors [6] and solar cells. [2a, 7] The functionalization of fullerenes does not only modifyt heir properties, but converts them into more processable forms, as pristine C 60 is only sparselys oluble in most solvents, making it intractable. Indeed, the quest for soluble fullerenes was (and still is) one of the main driving forces in the field of covalent modification of carbon nanostructures. Phenyl-C61-butyric-acid-methyl-ester (PCBM), af ullerened erivative, is as olution-processable n-type organic semiconductor,w hich is commonly blended with ptype conjugated polymers to make photovoltaic( PV) cells. However,o wing to the dependence of PV properties on frontier orbital energy levels of donor and acceptors, the application of PCBM to all donorp olymers irrespective of their optoelectronic properties leads to untrue PV properties. For instance,r eports by Susarova et al. [8] and Kästnere tal. [9] compared the PV responses of as et of polymers with PCBM and other functionalized fullerenes and observed that PCBM gave just moderate efficiencies in combination with the polymers, whereas the best PV performances were obtained with ab lend of each polymerw ith specific fullerened erivatives possessing better-suiting molecularstructures. Herein, we describe afulleropyrrolid...

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“…In 1985, fullerene was discovered as a third allotrope of carbon [12]. Because of its unusual spherical structure and unique physical and chemical properties, fullerene has attracted much attention for applications in life science and material science [13][14][15][16][17][18][19]. The desensitizing effects of fullerene and nitrofullerene derivatives on octogen (HMX) were investigated by our research group, and positive results have been obtained [20,21].…”

Section: Introductionmentioning

confidence: 99%

Combustion Effects of Nitrofulleropyrrolidine on RDX‐CMDB Propellants

Jin

Peng

Zhao

et al. 2014

Propellants Explo Pyrotec

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The effect of N‐methyl‐2‐(3‐nitrophenyl)pyrrolidino[3′,4′:1,2]fullerene (mNPF) on the decomposition characteristics of hexogen (RDX) was investigated using differential scanning calorimetry (DSC). The results show that mNPF can accelerate the decomposition of RDX, the peak temperature (Tp) of the exothermal decomposition is reduced by 6.4 K, and the corresponding apparent activation energy (Ea) is decreased by 8.7 kJ mol−1. N‐methyl‐2‐(3‐nitrophenyl)pyrrolidino[3′,4′:1,2]fullerene (mNPF), carbon black (CB), and C60 were used as combustion catalysts to improve the combustion performance of a composite modified double‐base propellant containing RDX (RDX‐CMDB). The burning rate experimental results show that mNPF has a stronger catalytic effect than C60 and CB. The magnitude of the effect of the three carbon substances on the enhancement of the burning rate is as follows: mNPF>C60>CB. The catalytic effects of different contents of mNPF on the burning rates of RDX‐CMDB propellants were also studied, and the results show that the burning rates of RDX‐CMDB propellants are improved with increasing mNPF content. The plateau burning rate of a RDX‐CMDB propellant can be increased to 19.6 mm s−1 when 1.0 % mNPF is added, and the corresponding plateau combustion region occurs at 8–22 MPa.

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Solution processable C60 fullerene-hydrazone dyads for optoelectronics

Cited by 12 publications

References 41 publications

Synthesis and Characterization of [60]Fullerene-Poly(glycidyl nitrate) and Its Thermal Decomposition

Synthesis and Characterization of [60]Fullerene-Poly(glycidyl nitrate) and Its Thermal Decomposition

Novel 5‐(Benzo[b]thiophen‐3‐yl)pyridine‐3‐carbaldehyde (BTPA) Functionalization Framework For Modulating Fullerene Electronics

Combustion Effects of Nitrofulleropyrrolidine on RDX‐CMDB Propellants

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