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Chernogolovka 2005

Poly(2-methoxy-5-(2`-ethyl-hexyloxy)-1,4-phenylene vinylene) (MEH-PPV)/nitrogen containing derivatives of fullerene composites: optical characterization and application in flexible polymer solar cells. N.G. Spitsina. Institute of Problems of Chemical Physics, Russian Academy of Sciences.

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Chernogolovka 2005

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  1. Poly(2-methoxy-5-(2`-ethyl-hexyloxy)-1,4-phenylene vinylene) (MEH-PPV)/nitrogen containing derivatives of fullerene composites: optical characterization and application in flexible polymer solar cells N.G. Spitsina Institute of Problems of Chemical Physics, Russian Academy of Sciences Chernogolovka 2005

  2. Milestones in Fullerene science 1985 “ this is the first example of a spferical aromatic molecule” 1990 Effective method of synthesis and purification 1991 Superconductivity of Na3C60 1993 Discovery of Photovoltaic (PV) phenomena in MEH-PPV/C60 Status now: the most promising application C60 is believed to be in photovoltaics Problems: Optimise the molecular ensembles Optimise the band structure Disorder in the polymer matrices The level of complexity approaching living cells

  3. Photovoltaic cell Photoinduced charge transfer. • Bilayer heterojunction – a donor and an • acceptor materials are stacked together • with a planar interface 2. “Bulk heterojunction” – adonor and an acceptor materials mix in the bulk • High Efficiency: • The compatibility between the conjugated polymer and the fullerene components • The morphology of the blend.

  4. azafulleroids aminofullerenes R N Nitrogen containing derivatives of [60]fullerene + +

  5. The cycloaddition reactions of C60 with organic azides 2-(Azahomo[60]fullereno)-5-nitropyrimidine (AFNP) 5-[5’-(azahomofullereno)pentyl]-1,3-diallyl-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione (AFDPIP) O,O-Dibutyl(azahomo[60]fullereno)phosphate (AFDBP) The reaction temperature: 100 to 180 C Solvent: o-dichlorobenzene Purification: column chromatography. The structure of the adducts: 13C NMR, 1H NMR, UV and IR spectroscopy. All = СН2СН=СН2 I. Romanova, O. Sinyashin, et.all. Mendeleev Commun, 2002, 51-5; Mendeleev Commun, 2000, 61-63; Russian Chemical Bulletin, Int. Ed., 2004, V. 53, No. 1. PP. 144-147.

  6. The reactions of C60 with cycloamines 1.tris(cyclopentilamine)hexahydrofullerene C60H3[NH(C5H9)]3 (CPA) 3.tetrakis(dibenzylamine)octahydrofullerene C60H4[NH(CH2-C6H5)]4 (BA) 2. tetrakis(benzylamine)octahydrofullerene C60H4[N(CH2-C6H5)2]4(DBA) The reaction temperature: 25 to 80 C Solvent: clorobenzene Purification: column chromatography. The structure of the adducts: 13C NMR, 1H NMR, UV and IR spectroscopy. N. Spitsina, I. Romanova, A. Lobach, et.all. Rus. Patent No. 2005122356. P.Deplano, E. Yagubskii, A.Lobach, N. Spitsina. Design and synthesis of molecular materials for optics and electronics, (2003) 360-364 Peak potentials of the first waves in the Cyclic voltamperometry of AFNP, AFDPIP, AFDBP, C60(BA)4, C60(DBA)4, C60(CPA)3 are 10 – 120 mV less negative than that of parent C60. (The peak potential of C60 measured in the same conditions is –0.83V.)

  7. Poly(2-methoxy-5-(2`-ethyl-hexyloxy)-1,4-phenylene vinylene) (MEH-PPV) AFM images of the surface morphology of MEH-PPV films Mn = 17400 - 40300 Mw= 76900 – 188500 [ŋ] = 0.46 – 5.16 dl/g I-V characteristics for the MEH-PPV film spun-cast from chlorobenzene solution. Belov M.Yu., Yakushchenko I.K., Kaplunov M.G.,et.all, Russian Patent No. 99125284 (1999), 2186821, RF 22 (2002).

  8. MEH-PPV/C60 composites were spin cast from solution into thin films. The host-guest structures of composites from different solvents.

  9. А) В) AFM images of the surface morphology of MEH-PPV/C60films (50 w.%) with thickness of ca. 100 nm

  10. . UV and IR spectra of MEH-PV/fullerene composite films Optical absorption spectraof MEH-PPV (solid line) MEH-PPV/AFNP(50 w.%) (dashed line) films onquarts. Infrared spectra of MEH-PPV film (1), AFNP in KBr pellet (2) and MEH-PPV/AFNP films with 5% (3) and 50% (4) AFNP The UV and IR spectra of MEH-PPV/fullerene films are simple superpositions of the spectra of the constituents: no ground-state interaction between the components

  11. Detector. Quarts box Argon atmos. Light filters vacuum 10-5 torr sample Magnetic field lens Polymer photoluminescence quenching by C60 Block-diagram of the photoluminescence setup The intensity of the 585 nm MEH-PPV PL band in MEH-PPV/fullerene as a function of the content of the fullerene Light irradiation Light source: 450 nm LED or a xenon lamp and a set of interference filters (400–650 nm), 20 mW/cm2 PC1000 plug-in spectrometer (Ocean Optics). Cell ressure: ~10-5 torr Room temperature Current measurements: Keithly 617 electrometer. AFNP (); AFDBP (); AFDPIP (); C60(DBA)4 (); C60(DBA)4 (+); C60(CPA)3 ().

  12. Transmission electron microphotographs of the MEH-PPV/C60 films Transmission electron microphotographs of the films of MEH-PPV/C60(50%) “Philips -301”, V=60 - 80 kV

  13. Transmission electron microphotographs of the MEH-PPV/AFN films (C) 30 % AFNP At high concentrations (about 50%), the C60 in the composite the film is weakly aggregated. On the contrary, AFNP at high concentration in the composite film forms large spherical agglomerates about 100-400 nm size. (A) 10 % AFNP; (Б) 50 % AFNP

  14. The photocurrent – voltage characteristics photovoltaic devices • I-V characteristics for the MEH-PPV() and MEH-PPV/AFNP photovoltaic devices with AFNP contents 10 (), 50 () and 75 ()%. • I-V characteristics for the MEH-PPV()and MEH-PPV/C60 photovoltaic devices with C60 contents 10 (--), 50 (o) and 75 (x) %.

  15. Conclusion • New soluble nitrogen containing organofullerenes of the organic amines and azides with the [60]fullerene. • The photocurrent in the PV with fullerene derivatives is two orders of magnitude higher than in the pure MEH-PPV. • The variation of the photoluminescence intensity with the volume percent of the C60 and the nitrogen containing organofullerenes offers a useful tool to control the charge transfer processes. • MEH-PPV polymer and the fullerene derivatives are promising materials for optoelectronic applications and for organic solar cells.

  16. Colaborators • M. Kaplunov, A. Lobach, I. Yakuschenko Institute of Problems of Chemical Physics, Russian Academy of Sciences, 142432 Chernogolovka, Russia; • I. Romanova A.E.Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Centre of Russian Academy of Sciences, Acad. Arbuzov str, 8, 420088 Kazan, Russia; • I. Tolstov, M. Triebel, E. Frankevich Institute of Energy Problems of Chemical Physics, Russian Academy of Sciences, Leninsky pr. 38/2, Moscow, 119334, Russia

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