Synthesis and Photoinduced Intramolecular Processes of Fulleropyrrolidine–Oligothienylenevinylene–Ferrocene Triads

作者: Frédéric Oswald , D.-M. Shafiqul Islam , Yasuyuki Araki , Vincent Troiani , Pilar de la Cruz

DOI: 10.1002/CHEM.200601889

关键词:

摘要: Two new triads based on N-methylfulleropyrolidine, oligothienylenevinylenes (nTV) and ferrocene (Fc), namely C(60)-nTV-Fc (n=2, 4) have been synthesized. A HOMO-LUMO gap as low 1.09-1.11 eV was experimentally determined by cyclic voltammetry. In both polar nonpolar solvents, photoinduced charge-separation (CS) processes in predominantly take place from the singlet excited states of C(60) nTV; this result indicated steady time-resolved emission spectroscopy. case C(60)-4TV-Fc, CS state nanosecond transient absorption spectra. C(60)-2TV-Fc, although process also confirmed fluorescence quenching lifetimes were shorter than those C(60)-4TV-Fc. It revealed that introduction Fc donor moiety at end longer nTV chain C(60)-nTV dyad systems effectively increases efficiency states.

参考文章(62)
H. W. Kroto, J. R. Heath, S. C. O’Brien, R. F. Curl, R. E. Smalley, C 60 : Buckminsterfullerene Nature. ,vol. 318, pp. 162- 163 ,(1985) , 10.1038/318162A0
James W. Arbogast, Christopher S. Foote, Michelle Kao, Electron transfer to triplet fullerene C60 Journal of the American Chemical Society. ,vol. 114, pp. 2277- 2279 ,(1992) , 10.1021/JA00032A063
K. Tamao, S. Kodama, I. Nakajima, M. Kumada, A. Minato, K. Suzuki, Nickel-phosphine complex-catalyzed Grignard coupling—II Tetrahedron. ,vol. 38, pp. 3347- 3354 ,(1982) , 10.1016/0040-4020(82)80117-8
Emmanuel Allard, Jack Cousseau, Jesus Ordúna, Javier Garín, Hongxia Luo, Yasuyuki Araki, Osamu Ito, Photoinduced electron-transfer processes in C60-tetrathiafulvalene dyads containing a short or long flexible spacer Physical Chemistry Chemical Physics. ,vol. 4, pp. 5944- 5951 ,(2002) , 10.1039/B206668H
Francis D'Souza, Melvin E. Zandler, Phillip M. Smith, Gollapalli R. Deviprasad, Klykov Arkady, Mamoru Fujitsuka, Osamu Ito, A Ferrocene-C60-Dinitrobenzene Triad: Synthesis and Computational, Electrochemical, and Photochemical Studies Journal of Physical Chemistry A. ,vol. 106, pp. 649- 656 ,(2002) , 10.1021/JP0136415
Emmanuel Allard, Jacques Delaunay, Fuyong Cheng, Jack Cousseau, Jesus Ordúna, Javier Garín, Novel C60-Based Building Blocks Derived from C602- Anion Organic Letters. ,vol. 3, pp. 3503- 3506 ,(2001) , 10.1021/OL0101786
A. Samanta, P.V. Kamat, Qenching of fullerene triplets by stable nitroxide radicals Chemical Physics Letters. ,vol. 199, pp. 635- 639 ,(1992) , 10.1016/0009-2614(92)85023-4
C. Martineau, P. Blanchard, D. Rondeau, J. Delaunay, J. Roncali, Synthesis and electronic properties of adducts of oligothienylenevinylenes and fullerene C60 Advanced Materials. ,vol. 14, pp. 283- 287 ,(2002) , 10.1002/1521-4095(20020219)14:4<283::AID-ADMA283>3.0.CO;2-M
K. George Thomas, V. Biju, M. V. George, Dirk M. Guldi, Prashant V. Kamat, Excited-State Interactions in Pyrrolidinofullerenes Journal of Physical Chemistry A. ,vol. 102, pp. 5341- 5348 ,(1998) , 10.1021/JP972756Z
Mamoru Fujitsuka, Akito Masuhara, Hitoshi Kasai, Hidetoshi Oikawa, Hachiro Nakanishi, Osamu Ito, Takashi Yamashiro, Yoshio Aso, Tetsuo Otsubo, None, Photoinduced charge separation and recombination processes in fine particles of oligothiophene-C60 dyad molecules Journal of Physical Chemistry B. ,vol. 105, pp. 9930- 9934 ,(2001) , 10.1021/JP0115796